KR20100137473A

KR20100137473A - 동통 치료를 위한 벨록세핀, 이의 거울상이성질체, 및 이의 유사체

동통 치료를 위한 벨록세핀, 이의 거울상이성질체, 및 이의 유사체 Download PDF

Info

Publication number: KR20100137473A
Authority: KR; South Korea
Prior art keywords: beloxepin; pain; composition; mammal; enantiomerically pure
Prior art date: 2008-02-19
Legal status : Withdrawn

Application number

KR1020107021010A

Other languages

English (en)

Korean (ko)

Inventor

부르도넥 베르트랑 르

롤랜드 돌

Original Assignee

아돌로 코포레이션

Priority date

2008-02-19

Filing date

2009-02-19

Publication date

2010-12-30

2009-02-19 Application filed by 아돌로 코포레이션 filed Critical 아돌로 코포레이션

2010-12-30 Publication of KR20100137473A publication Critical patent/KR20100137473A/ko

Status Withdrawn legal-status Critical Current

Links

229950003852 beloxepin Drugs 0.000 title claims abstract description 565
RPMDQAYGQBREBS-LPHOPBHVSA-N beloxepin Chemical compound O1C2=CC=CC=C2[C@@]2(O)CCN(C)C[C@H]2C2=CC=CC(C)=C21 RPMDQAYGQBREBS-LPHOPBHVSA-N 0.000 title claims abstract description 308
208000002193 Pain Diseases 0.000 title claims abstract description 275
230000036407 pain Effects 0.000 title claims abstract description 238
238000011282 treatment Methods 0.000 title claims description 93
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title claims description 41
238000000034 method Methods 0.000 claims abstract description 110
239000000203 mixture Substances 0.000 claims description 229
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 103
150000001875 compounds Chemical class 0.000 claims description 80
201000010099 disease Diseases 0.000 claims description 70
150000003839 salts Chemical class 0.000 claims description 48
241000124008 Mammalia Species 0.000 claims description 33
208000035475 disorder Diseases 0.000 claims description 33
239000005557 antagonist Substances 0.000 claims description 32
230000003040 nociceptive effect Effects 0.000 claims description 28
208000004296 neuralgia Diseases 0.000 claims description 26
208000033808 peripheral neuropathy Diseases 0.000 claims description 24
208000019901 Anxiety disease Diseases 0.000 claims description 23
208000000094 Chronic Pain Diseases 0.000 claims description 21
201000001119 neuropathy Diseases 0.000 claims description 21
230000007823 neuropathy Effects 0.000 claims description 21
206010065390 Inflammatory pain Diseases 0.000 claims description 20
230000001154 acute effect Effects 0.000 claims description 19
208000021722 neuropathic pain Diseases 0.000 claims description 19
241000282412 Homo Species 0.000 claims description 16
208000002551 irritable bowel syndrome Diseases 0.000 claims description 16
208000001294 Nociceptive Pain Diseases 0.000 claims description 14
208000005298 acute pain Diseases 0.000 claims description 14
208000032131 Diabetic Neuropathies Diseases 0.000 claims description 13
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 13
206010022437 insomnia Diseases 0.000 claims description 13
238000001727 in vivo Methods 0.000 claims description 11
201000000980 schizophrenia Diseases 0.000 claims description 10
102000056834 5-HT2 Serotonin Receptors Human genes 0.000 claims description 9
108091005479 5-HT2 receptors Proteins 0.000 claims description 9
208000019022 Mood disease Diseases 0.000 claims description 9
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 9
208000010877 cognitive disease Diseases 0.000 claims description 9
208000019695 Migraine disease Diseases 0.000 claims description 8
208000010886 Peripheral nerve injury Diseases 0.000 claims description 8
208000028017 Psychotic disease Diseases 0.000 claims description 8
201000006417 multiple sclerosis Diseases 0.000 claims description 8
201000008482 osteoarthritis Diseases 0.000 claims description 8
208000019906 panic disease Diseases 0.000 claims description 8
206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
206010044652 trigeminal neuralgia Diseases 0.000 claims description 8
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
208000030814 Eating disease Diseases 0.000 claims description 7
208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
235000014632 disordered eating Nutrition 0.000 claims description 7
206010027599 migraine Diseases 0.000 claims description 7
239000003215 serotonin 5-HT2 receptor antagonist Substances 0.000 claims description 7
208000000103 Anorexia Nervosa Diseases 0.000 claims description 6
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
208000001640 Fibromyalgia Diseases 0.000 claims description 6
208000020339 Spinal injury Diseases 0.000 claims description 6
208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 6
230000009977 dual effect Effects 0.000 claims description 6
238000000338 in vitro Methods 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
208000028173 post-traumatic stress disease Diseases 0.000 claims description 6
206010006550 Bulimia nervosa Diseases 0.000 claims description 5
206010026749 Mania Diseases 0.000 claims description 5
206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 5
208000006673 asthma Diseases 0.000 claims description 5
201000002859 sleep apnea Diseases 0.000 claims description 5
208000009935 visceral pain Diseases 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 4
206010069632 Bladder dysfunction Diseases 0.000 claims description 4
208000005171 Dysmenorrhea Diseases 0.000 claims description 4
201000009273 Endometriosis Diseases 0.000 claims description 4
206010021639 Incontinence Diseases 0.000 claims description 4
208000006399 Premature Obstetric Labor Diseases 0.000 claims description 4
208000007536 Thrombosis Diseases 0.000 claims description 4
201000001881 impotence Diseases 0.000 claims description 4
206010027175 memory impairment Diseases 0.000 claims description 4
238000007634 remodeling Methods 0.000 claims description 4
239000002400 serotonin 2A antagonist Substances 0.000 claims description 4
208000018737 Parkinson disease Diseases 0.000 claims description 3
230000003042 antagnostic effect Effects 0.000 claims description 3
238000007911 parenteral administration Methods 0.000 claims description 3
208000022821 personality disease Diseases 0.000 claims description 3
239000002891 serotonin 2B antagonist Substances 0.000 claims description 3
239000002484 serotonin 2C antagonist Substances 0.000 claims description 3
206010001497 Agitation Diseases 0.000 claims description 2
206010013935 Dysmenorrhoea Diseases 0.000 claims description 2
208000010228 Erectile Dysfunction Diseases 0.000 claims description 2
206010036618 Premenstrual syndrome Diseases 0.000 claims description 2
208000003251 Pruritus Diseases 0.000 claims description 2
208000013403 hyperactivity Diseases 0.000 claims description 2
208000028867 ischemia Diseases 0.000 claims description 2
208000016686 tic disease Diseases 0.000 claims description 2
206010058019 Cancer Pain Diseases 0.000 claims 4
206010067269 Uterine fibrosis Diseases 0.000 claims 1
230000002085 persistent effect Effects 0.000 claims 1
208000016153 withdrawal disease Diseases 0.000 claims 1
241000700159 Rattus Species 0.000 description 87
239000003814 drug Substances 0.000 description 44
230000003574 anti-allodynic effect Effects 0.000 description 42
239000002253 acid Substances 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
102000005962 receptors Human genes 0.000 description 39
108020003175 receptors Proteins 0.000 description 39
230000000694 effects Effects 0.000 description 34
238000001356 surgical procedure Methods 0.000 description 34
208000024891 symptom Diseases 0.000 description 34
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
101000896576 Homo sapiens Putative cytochrome P450 2D7 Proteins 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
229940079593 drug Drugs 0.000 description 33
102100021702 Putative cytochrome P450 2D7 Human genes 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
208000004454 Hyperalgesia Diseases 0.000 description 28
238000002648 combination therapy Methods 0.000 description 28
238000012360 testing method Methods 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
238000002474 experimental method Methods 0.000 description 27
241001465754 Metazoa Species 0.000 description 26
230000005764 inhibitory process Effects 0.000 description 26
239000003981 vehicle Substances 0.000 description 26
-1 quetierine Chemical compound 0.000 description 25
239000003795 chemical substances by application Substances 0.000 description 22
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 20
230000001225 therapeutic effect Effects 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 18
238000002360 preparation method Methods 0.000 description 18
239000000243 solution Substances 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
239000010410 layer Substances 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
238000003556 assay Methods 0.000 description 15
229930003827 cannabinoid Natural products 0.000 description 15
239000003557 cannabinoid Substances 0.000 description 15
108010078791 Carrier Proteins Proteins 0.000 description 14
239000003112 inhibitor Substances 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 14
238000005481 NMR spectroscopy Methods 0.000 description 13
102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 description 13
108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
230000036506 anxiety Effects 0.000 description 13
229940065144 cannabinoids Drugs 0.000 description 13
230000000875 corresponding effect Effects 0.000 description 13
238000011808 rodent model Methods 0.000 description 13
208000011580 syndromic disease Diseases 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
230000004044 response Effects 0.000 description 12
230000003502 anti-nociceptive effect Effects 0.000 description 11
230000002981 neuropathic effect Effects 0.000 description 11
229940005483 opioid analgesics Drugs 0.000 description 11
208000019116 sleep disease Diseases 0.000 description 11
206010028980 Neoplasm Diseases 0.000 description 10
201000011510 cancer Diseases 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
208000037765 diseases and disorders Diseases 0.000 description 10
229910052739 hydrogen Inorganic materials 0.000 description 10
230000001404 mediated effect Effects 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
102100033928 Sodium-dependent dopamine transporter Human genes 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000000730 antalgic agent Substances 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
239000012458 free base Substances 0.000 description 9
229960005181 morphine Drugs 0.000 description 9
239000000047 product Substances 0.000 description 9
229940076279 serotonin Drugs 0.000 description 9
238000010561 standard procedure Methods 0.000 description 9
229940124597 therapeutic agent Drugs 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
229940035676 analgesics Drugs 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
238000010171 animal model Methods 0.000 description 8
230000004071 biological effect Effects 0.000 description 8
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 8
238000011534 incubation Methods 0.000 description 8
238000001990 intravenous administration Methods 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
150000007524 organic acids Chemical class 0.000 description 8
208000020016 psychiatric disease Diseases 0.000 description 8
229960003770 reboxetine Drugs 0.000 description 8
CBQGYUDMJHNJBX-RTBURBONSA-N reboxetine Chemical compound CCOC1=CC=CC=C1O[C@H](C=1C=CC=CC=1)[C@@H]1OCCNC1 CBQGYUDMJHNJBX-RTBURBONSA-N 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 description 7
208000020401 Depressive disease Diseases 0.000 description 7
108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 description 7
MKXZASYAUGDDCJ-SZMVWBNQSA-N LSM-2525 Chemical compound C1CCC[C@H]2[C@@]3([H])N(C)CC[C@]21C1=CC(OC)=CC=C1C3 MKXZASYAUGDDCJ-SZMVWBNQSA-N 0.000 description 7
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
230000027455 binding Effects 0.000 description 7
229960001985 dextromethorphan Drugs 0.000 description 7
229960002866 duloxetine Drugs 0.000 description 7
208000014674 injury Diseases 0.000 description 7
230000000670 limiting effect Effects 0.000 description 7
238000005259 measurement Methods 0.000 description 7
230000036470 plasma concentration Effects 0.000 description 7
230000003389 potentiating effect Effects 0.000 description 7
229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 7
239000007787 solid Substances 0.000 description 7
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 6
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
206010053552 allodynia Diseases 0.000 description 6
239000000935 antidepressant agent Substances 0.000 description 6
229940005513 antidepressants Drugs 0.000 description 6
230000008901 benefit Effects 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
210000004978 chinese hamster ovary cell Anatomy 0.000 description 6
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 6
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 6
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
230000007774 longterm Effects 0.000 description 6
239000012528 membrane Substances 0.000 description 6
150000007522 mineralic acids Chemical class 0.000 description 6
TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical group OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 6
230000009871 nonspecific binding Effects 0.000 description 6
235000005985 organic acids Nutrition 0.000 description 6
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical group OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 6
238000000926 separation method Methods 0.000 description 6
230000002889 sympathetic effect Effects 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
230000009278 visceral effect Effects 0.000 description 6
208000035154 Hyperesthesia Diseases 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 5
229960000836 amitriptyline Drugs 0.000 description 5
208000022531 anorexia Diseases 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
230000006378 damage Effects 0.000 description 5
206010061428 decreased appetite Diseases 0.000 description 5
231100000673 dose–response relationship Toxicity 0.000 description 5
201000006549 dyspepsia Diseases 0.000 description 5
208000021302 gastroesophageal reflux disease Diseases 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
230000003834 intracellular effect Effects 0.000 description 5
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
230000007958 sleep Effects 0.000 description 5
239000000126 substance Substances 0.000 description 5
230000000699 topical effect Effects 0.000 description 5
230000008733 trauma Effects 0.000 description 5
TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 description 4
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
206010002650 Anorexia nervosa and bulimia Diseases 0.000 description 4
206010012289 Dementia Diseases 0.000 description 4
206010020772 Hypertension Diseases 0.000 description 4
108010044467 Isoenzymes Proteins 0.000 description 4
PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 4
101150053185 P450 gene Proteins 0.000 description 4
206010041250 Social phobia Diseases 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
229940123445 Tricyclic antidepressant Drugs 0.000 description 4
230000009102 absorption Effects 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
239000002671 adjuvant Substances 0.000 description 4
230000006399 behavior Effects 0.000 description 4
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
230000001684 chronic effect Effects 0.000 description 4
229960004126 codeine Drugs 0.000 description 4
238000010520 demethylation reaction Methods 0.000 description 4
XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
239000000835 fiber Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
238000007912 intraperitoneal administration Methods 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
230000001537 neural effect Effects 0.000 description 4
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000000159 protein binding assay Methods 0.000 description 4
230000035945 sensitivity Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000004611 spectroscopical analysis Methods 0.000 description 4
230000000638 stimulation Effects 0.000 description 4
208000011117 substance-related disease Diseases 0.000 description 4
230000002194 synthesizing effect Effects 0.000 description 4
239000003826 tablet Substances 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
229960004380 tramadol Drugs 0.000 description 4
TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 description 4
239000003029 tricyclic antidepressant agent Substances 0.000 description 4
AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 3
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 3
SSNHGLKFJISNTR-FWUPRJFYSA-N (6ar,10ar)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol;2-[(6r)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol Chemical compound OC1=CC(CCCCC)=CC(O)=C1C1[C@H](C(C)=C)CCC(C)=C1.C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 SSNHGLKFJISNTR-FWUPRJFYSA-N 0.000 description 3
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 3
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
RGSVXQJPSWZXOP-UHFFFAOYSA-N 1-[1-(1-benzothiophen-2-yl)cyclohexyl]piperidine Chemical compound C1CCCCN1C1(C=2SC3=CC=CC=C3C=2)CCCCC1 RGSVXQJPSWZXOP-UHFFFAOYSA-N 0.000 description 3
AMMPLVWPWSYRDR-UHFFFAOYSA-N 1-methylbicyclo[2.2.2]oct-2-ene-4-carboxylic acid Chemical compound C1CC2(C(O)=O)CCC1(C)C=C2 AMMPLVWPWSYRDR-UHFFFAOYSA-N 0.000 description 3
UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical group C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 3
XLZYKTYMLBOINK-UHFFFAOYSA-N 3-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C(=O)C=2C=CC(O)=CC=2)=C1 XLZYKTYMLBOINK-UHFFFAOYSA-N 0.000 description 3
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 3
JTWMBPZRYBLNNG-UHFFFAOYSA-N 4-(aminomethyl)-7-methoxychromen-2-one Chemical compound NCC1=CC(=O)OC2=CC(OC)=CC=C21 JTWMBPZRYBLNNG-UHFFFAOYSA-N 0.000 description 3
RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
208000024172 Cardiovascular disease Diseases 0.000 description 3
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 3
208000007220 Cytochrome P-450 CYP2D6 Inhibitors Diseases 0.000 description 3
108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 3
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Chemical group OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 3
206010012374 Depressed mood Diseases 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
206010016654 Fibrosis Diseases 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
208000010412 Glaucoma Diseases 0.000 description 3
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Chemical group OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
206010019196 Head injury Diseases 0.000 description 3
GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 3
208000033830 Hot Flashes Diseases 0.000 description 3
206010060800 Hot flush Diseases 0.000 description 3
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical group OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
206010027304 Menopausal symptoms Diseases 0.000 description 3
TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Chemical group OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
235000021314 Palmitic acid Nutrition 0.000 description 3
206010033645 Pancreatitis Diseases 0.000 description 3
206010033647 Pancreatitis acute Diseases 0.000 description 3
AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 3
206010039897 Sedation Diseases 0.000 description 3
201000001880 Sexual dysfunction Diseases 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
102100028874 Sodium-dependent serotonin transporter Human genes 0.000 description 3
208000010040 Sprains and Strains Diseases 0.000 description 3
235000021355 Stearic acid Nutrition 0.000 description 3
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
201000004810 Vascular dementia Diseases 0.000 description 3
201000003229 acute pancreatitis Diseases 0.000 description 3
238000005273 aeration Methods 0.000 description 3
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
230000004075 alteration Effects 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
230000003070 anti-hyperalgesia Effects 0.000 description 3
229940121363 anti-inflammatory agent Drugs 0.000 description 3
239000002260 anti-inflammatory agent Substances 0.000 description 3
238000013459 approach Methods 0.000 description 3
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 3
229940092714 benzenesulfonic acid Drugs 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 3
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
239000000969 carrier Substances 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
235000013985 cinnamic acid Nutrition 0.000 description 3
229930016911 cinnamic acid Natural products 0.000 description 3
235000015165 citric acid Nutrition 0.000 description 3
229960003920 cocaine Drugs 0.000 description 3
239000002475 cognitive enhancer Substances 0.000 description 3
238000012875 competitive assay Methods 0.000 description 3
229960002069 diamorphine Drugs 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
238000001647 drug administration Methods 0.000 description 3
230000002996 emotional effect Effects 0.000 description 3
206010015037 epilepsy Diseases 0.000 description 3
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 3
230000004761 fibrosis Effects 0.000 description 3
238000012921 fluorescence analysis Methods 0.000 description 3
239000001530 fumaric acid Substances 0.000 description 3
235000011087 fumaric acid Nutrition 0.000 description 3
230000006870 function Effects 0.000 description 3
230000030135 gastric motility Effects 0.000 description 3
210000001035 gastrointestinal tract Anatomy 0.000 description 3
239000000174 gluconic acid Chemical group 0.000 description 3
235000012208 gluconic acid Nutrition 0.000 description 3
239000004220 glutamic acid Chemical group 0.000 description 3
235000013922 glutamic acid Nutrition 0.000 description 3
208000003906 hydrocephalus Diseases 0.000 description 3
230000004941 influx Effects 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
230000004410 intraocular pressure Effects 0.000 description 3
239000004310 lactic acid Substances 0.000 description 3
235000014655 lactic acid Nutrition 0.000 description 3
239000007788 liquid Substances 0.000 description 3
210000001853 liver microsome Anatomy 0.000 description 3
208000024714 major depressive disease Diseases 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
239000011976 maleic acid Substances 0.000 description 3
239000001630 malic acid Substances 0.000 description 3
235000011090 malic acid Nutrition 0.000 description 3
229960002510 mandelic acid Drugs 0.000 description 3
230000015654 memory Effects 0.000 description 3
239000003695 memory enhancer Substances 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
230000004899 motility Effects 0.000 description 3
208000010125 myocardial infarction Diseases 0.000 description 3
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 3
201000003631 narcolepsy Diseases 0.000 description 3
210000005036 nerve Anatomy 0.000 description 3
239000003176 neuroleptic agent Substances 0.000 description 3
230000000926 neurological effect Effects 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 3
229960002748 norepinephrine Drugs 0.000 description 3
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 3
229960001158 nortriptyline Drugs 0.000 description 3
231100000862 numbness Toxicity 0.000 description 3
230000000414 obstructive effect Effects 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Chemical group OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
229960002296 paroxetine Drugs 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000006187 pill Substances 0.000 description 3
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
206010035653 pneumoconiosis Diseases 0.000 description 3
WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 3
239000000651 prodrug Substances 0.000 description 3
229940002612 prodrug Drugs 0.000 description 3
230000000069 prophylactic effect Effects 0.000 description 3
235000019260 propionic acid Nutrition 0.000 description 3
208000002815 pulmonary hypertension Diseases 0.000 description 3
229940107700 pyruvic acid Drugs 0.000 description 3
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
238000001525 receptor binding assay Methods 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
208000023504 respiratory system disease Diseases 0.000 description 3
229960004889 salicylic acid Drugs 0.000 description 3
230000036280 sedation Effects 0.000 description 3
231100000872 sexual dysfunction Toxicity 0.000 description 3
239000008117 stearic acid Chemical group 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000758 substrate Substances 0.000 description 3
230000002459 sustained effect Effects 0.000 description 3
230000009885 systemic effect Effects 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
230000008719 thickening Effects 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
238000012546 transfer Methods 0.000 description 3
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
CBQGYUDMJHNJBX-OALUTQOASA-N (2S)-2-[(S)-(2-ethoxyphenoxy)-phenylmethyl]morpholine Chemical compound CCOC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 CBQGYUDMJHNJBX-OALUTQOASA-N 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
LVYLCBNXHHHPSB-UHFFFAOYSA-N 2-hydroxyethyl salicylate Chemical compound OCCOC(=O)C1=CC=CC=C1O LVYLCBNXHHHPSB-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 2
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
108010087765 Antipain Proteins 0.000 description 2
206010002869 Anxiety symptoms Diseases 0.000 description 2
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
208000032841 Bulimia Diseases 0.000 description 2
239000002083 C09CA01 - Losartan Substances 0.000 description 2
108091006146 Channels Proteins 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
102000003849 Cytochrome P450 Human genes 0.000 description 2
OGDVEMNWJVYAJL-LEPYJNQMSA-N Ethyl morphine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OCC OGDVEMNWJVYAJL-LEPYJNQMSA-N 0.000 description 2
OGDVEMNWJVYAJL-UHFFFAOYSA-N Ethylmorphine Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OCC OGDVEMNWJVYAJL-UHFFFAOYSA-N 0.000 description 2
208000027776 Extrapyramidal disease Diseases 0.000 description 2
208000007882 Gastritis Diseases 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
206010019233 Headaches Diseases 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
206010020751 Hypersensitivity Diseases 0.000 description 2
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
208000005615 Interstitial Cystitis Diseases 0.000 description 2
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
206010027590 Middle insomnia Diseases 0.000 description 2
229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 2
206010027951 Mood swings Diseases 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
DEXMFYZAHXMZNM-UHFFFAOYSA-N Narceine Chemical compound OC(=O)C1=C(OC)C(OC)=CC=C1C(=O)CC1=C(CCN(C)C)C=C(OCO2)C2=C1OC DEXMFYZAHXMZNM-UHFFFAOYSA-N 0.000 description 2
206010029216 Nervousness Diseases 0.000 description 2
BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 description 2
RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229940124639 Selective inhibitor Drugs 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
101710114615 Sodium-dependent dopamine transporter Proteins 0.000 description 2
206010072005 Spinal pain Diseases 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
239000012317 TBTU Substances 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 2
229960001138 acetylsalicylic acid Drugs 0.000 description 2
230000009471 action Effects 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
230000001430 anti-depressive effect Effects 0.000 description 2
SDNYTAYICBFYFH-TUFLPTIASA-N antipain Chemical compound NC(N)=NCCC[C@@H](C=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 SDNYTAYICBFYFH-TUFLPTIASA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000006793 arrhythmia Effects 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
229960002430 atomoxetine Drugs 0.000 description 2
VHGCDTVCOLNTBX-QGZVFWFLSA-N atomoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=CC=C1C VHGCDTVCOLNTBX-QGZVFWFLSA-N 0.000 description 2
230000002567 autonomic effect Effects 0.000 description 2
230000004888 barrier function Effects 0.000 description 2
229940049706 benzodiazepine Drugs 0.000 description 2
150000001557 benzodiazepines Chemical class 0.000 description 2
230000000740 bleeding effect Effects 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
239000012267 brine Substances 0.000 description 2
229960001948 caffeine Drugs 0.000 description 2
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 2
210000001175 cerebrospinal fluid Anatomy 0.000 description 2
239000007958 cherry flavor Substances 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
238000000576 coating method Methods 0.000 description 2
230000019771 cognition Effects 0.000 description 2
230000008602 contraction Effects 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000003001 depressive effect Effects 0.000 description 2
229960004193 dextropropoxyphene Drugs 0.000 description 2
XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 2
229960001259 diclofenac Drugs 0.000 description 2
DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 2
RBOXVHNMENFORY-DNJOTXNNSA-N dihydrocodeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC RBOXVHNMENFORY-DNJOTXNNSA-N 0.000 description 2
229960000920 dihydrocodeine Drugs 0.000 description 2
239000002612 dispersion medium Substances 0.000 description 2
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical group CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
229940043264 dodecyl sulfate Drugs 0.000 description 2
229960003638 dopamine Drugs 0.000 description 2
206010013663 drug dependence Diseases 0.000 description 2
230000036267 drug metabolism Effects 0.000 description 2
230000008451 emotion Effects 0.000 description 2
238000003821 enantio-separation Methods 0.000 description 2
229950008247 esreboxetine Drugs 0.000 description 2
229960004578 ethylmorphine Drugs 0.000 description 2
229960002428 fentanyl Drugs 0.000 description 2
PJMPHNIQZUBGLI-UHFFFAOYSA-N fentanyl Chemical compound C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 PJMPHNIQZUBGLI-UHFFFAOYSA-N 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
231100000869 headache Toxicity 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
230000003054 hormonal effect Effects 0.000 description 2
LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 description 2
229960000240 hydrocodone Drugs 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
229940071870 hydroiodic acid Drugs 0.000 description 2
229960001680 ibuprofen Drugs 0.000 description 2
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
230000006872 improvement Effects 0.000 description 2
208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 2
230000002757 inflammatory effect Effects 0.000 description 2
210000000936 intestine Anatomy 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
FPCCSQOGAWCVBH-UHFFFAOYSA-N ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000003446 ligand Substances 0.000 description 2
KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 2
229960004773 losartan Drugs 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000012423 maintenance Methods 0.000 description 2
229960004090 maprotiline Drugs 0.000 description 2
QSLMDECMDJKHMQ-GSXCWMCISA-N maprotiline Chemical compound C12=CC=CC=C2[C@@]2(CCCNC)C3=CC=CC=C3[C@@H]1CC2 QSLMDECMDJKHMQ-GSXCWMCISA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
230000003340 mental effect Effects 0.000 description 2
230000002503 metabolic effect Effects 0.000 description 2
210000001589 microsome Anatomy 0.000 description 2
239000002899 monoamine oxidase inhibitor Substances 0.000 description 2
230000036651 mood Effects 0.000 description 2
238000002552 multiple reaction monitoring Methods 0.000 description 2
229960002715 nicotine Drugs 0.000 description 2
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
231100000957 no side effect Toxicity 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical group O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 description 2
229960002085 oxycodone Drugs 0.000 description 2
229960005489 paracetamol Drugs 0.000 description 2
239000002245 particle Substances 0.000 description 2
229960000762 perphenazine Drugs 0.000 description 2
208000019899 phobic disease Diseases 0.000 description 2
RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 2
239000000902 placebo Substances 0.000 description 2
229940068196 placebo Drugs 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
230000002335 preservative effect Effects 0.000 description 2
230000002265 prevention Effects 0.000 description 2
235000018102 proteins Nutrition 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
230000009103 reabsorption Effects 0.000 description 2
238000011160 research Methods 0.000 description 2
208000012672 seasonal affective disease Diseases 0.000 description 2
239000000932 sedative agent Substances 0.000 description 2
230000007281 self degradation Effects 0.000 description 2
230000035807 sensation Effects 0.000 description 2
235000019615 sensations Nutrition 0.000 description 2
239000003772 serotonin uptake inhibitor Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
238000003860 storage Methods 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
210000003568 synaptosome Anatomy 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
238000011200 topical administration Methods 0.000 description 2
LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 2
210000004291 uterus Anatomy 0.000 description 2
230000004580 weight loss Effects 0.000 description 2
208000016261 weight loss Diseases 0.000 description 2
UVITTYOJFDLOGI-UHFFFAOYSA-N (1,2,5-trimethyl-4-phenylpiperidin-4-yl) propanoate Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CC(C)N(C)CC1C UVITTYOJFDLOGI-UHFFFAOYSA-N 0.000 description 1
OQANPHBRHBJGNZ-FYJGNVAPSA-N (3e)-6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid Chemical compound C1=CC(=O)C(C(=O)O)=C\C1=N\NC1=CC=C(S(=O)(=O)NC=2N=CC=CC=2)C=C1 OQANPHBRHBJGNZ-FYJGNVAPSA-N 0.000 description 1
LGFMXOTUSSVQJV-NEYUFSEYSA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;(4r,4ar,7s,7ar,12bs)-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol;1-[(3,4-dimethoxyphenyl)methyl]-6 Chemical compound Cl.Cl.Cl.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 LGFMXOTUSSVQJV-NEYUFSEYSA-N 0.000 description 1
RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WFJFGMLKAISFOZ-UHFFFAOYSA-N 1-amino-3-iminourea Chemical compound NN=C(O)N=N WFJFGMLKAISFOZ-UHFFFAOYSA-N 0.000 description 1
GKHIHRYGKFTENO-UHFFFAOYSA-N 1-methyl-6h-benzo[b][1]benzoxepin-5-one Chemical compound O1C2=CC=CC=C2CC(=O)C2=C1C(C)=CC=C2 GKHIHRYGKFTENO-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
HJOCKFVCMLCPTP-UHFFFAOYSA-N 2-[(2-ethoxyphenoxy)methyl]morpholine;hydron;chloride Chemical compound Cl.CCOC1=CC=CC=C1OCC1OCCNC1 HJOCKFVCMLCPTP-UHFFFAOYSA-N 0.000 description 1
XLVXAUNDHWERBM-IVGWJTKZSA-N 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide Chemical compound CC1=C(CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 XLVXAUNDHWERBM-IVGWJTKZSA-N 0.000 description 1
POVNAACPWRUALM-UHFFFAOYSA-N 2-[2-(2-methylphenoxy)phenyl]acetic acid Chemical compound CC1=CC=CC=C1OC1=CC=CC=C1CC(O)=O POVNAACPWRUALM-UHFFFAOYSA-N 0.000 description 1
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
SHXWCVYOXRDMCX-UHFFFAOYSA-N 3,4-methylenedioxymethamphetamine Chemical compound CNC(C)CC1=CC=C2OCOC2=C1 SHXWCVYOXRDMCX-UHFFFAOYSA-N 0.000 description 1
ITJNARMNRKSWTA-RLXJOQACSA-N 3-(2-methoxyphenoxy)-3-phenyl-n-(tritritiomethyl)propan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC([3H])([3H])[3H])OC1=CC=CC=C1OC ITJNARMNRKSWTA-RLXJOQACSA-N 0.000 description 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
PMXMIIMHBWHSKN-UHFFFAOYSA-N 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCC(O)C4=NC=3C)=NOC2=C1 PMXMIIMHBWHSKN-UHFFFAOYSA-N 0.000 description 1
HVMBPUABKRKNPU-UHFFFAOYSA-N 4-(aminomethyl)-7-hydroxychromen-2-one Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2CN HVMBPUABKRKNPU-UHFFFAOYSA-N 0.000 description 1
SFLSHLFXELFNJZ-CMIMLBRMSA-N 4-[(1r)-2-amino-1-hydroxy-1-tritioethyl]benzene-1,2-diol Chemical compound NC[C@@](O)([3H])C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-CMIMLBRMSA-N 0.000 description 1
KNKRHSVKIORZQB-UHFFFAOYSA-N 4-bromo-2-(hydroxymethyl)phenol Chemical compound OCC1=CC(Br)=CC=C1O KNKRHSVKIORZQB-UHFFFAOYSA-N 0.000 description 1
IMKNHLPRDSWAHW-UHFFFAOYSA-N 4-butyl-1,2-diphenylpyrazolidine-3,5-dione;4,5-dihydro-1,3-thiazol-2-amine Chemical compound NC1=NCCS1.O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 IMKNHLPRDSWAHW-UHFFFAOYSA-N 0.000 description 1
102000049773 5-HT2A Serotonin Receptor Human genes 0.000 description 1
102000006969 5-HT2B Serotonin Receptor Human genes 0.000 description 1
DVEQCIBLXRSYPH-UHFFFAOYSA-N 5-butyl-1-cyclohexylbarbituric acid Chemical compound O=C1C(CCCC)C(=O)NC(=O)N1C1CCCCC1 DVEQCIBLXRSYPH-UHFFFAOYSA-N 0.000 description 1
SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
XKFPYPQQHFEXRZ-UHFFFAOYSA-N 5-methyl-N'-(phenylmethyl)-3-isoxazolecarbohydrazide Chemical compound O1C(C)=CC(C(=O)NNCC=2C=CC=CC=2)=N1 XKFPYPQQHFEXRZ-UHFFFAOYSA-N 0.000 description 1
LVRVABPNVHYXRT-BQWXUCBYSA-N 52906-92-0 Chemical compound C([C@H](N)C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(O)=O)C(C)C)C1=CC=CC=C1 LVRVABPNVHYXRT-BQWXUCBYSA-N 0.000 description 1
USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 1
208000007848 Alcoholism Diseases 0.000 description 1
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 description 1
206010003225 Arteriospasm coronary Diseases 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
206010003591 Ataxia Diseases 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
208000020925 Bipolar disease Diseases 0.000 description 1
241000167854 Bourreria succulenta Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
DXHRAGITLXXPCC-UHFFFAOYSA-N C(CCCCCCCCCCC)OS(O)(=O)=O.C(CCC)CC(=O)O Chemical group C(CCCCCCCCCCC)OS(O)(=O)=O.C(CCC)CC(=O)O DXHRAGITLXXPCC-UHFFFAOYSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
206010048610 Cardiotoxicity Diseases 0.000 description 1
206010008479 Chest Pain Diseases 0.000 description 1
108010009685 Cholinergic Receptors Proteins 0.000 description 1
OIRAEJWYWSAQNG-UHFFFAOYSA-N Clidanac Chemical compound ClC=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 OIRAEJWYWSAQNG-UHFFFAOYSA-N 0.000 description 1
208000003890 Coronary Vasospasm Diseases 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
241000699802 Cricetulus griseus Species 0.000 description 1
208000014311 Cushing syndrome Diseases 0.000 description 1
102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 1
HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
239000012848 Dextrorphan Substances 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
IJVCSMSMFSCRME-KBQPJGBKSA-N Dihydromorphine Chemical compound O([C@H]1[C@H](CC[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O IJVCSMSMFSCRME-KBQPJGBKSA-N 0.000 description 1
206010013654 Drug abuse Diseases 0.000 description 1
206010013980 Dyssomnias Diseases 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
208000017701 Endocrine disease Diseases 0.000 description 1
206010016275 Fear Diseases 0.000 description 1
241000233866 Fungi Species 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
240000001238 Gaultheria procumbens Species 0.000 description 1
235000007297 Gaultheria procumbens Nutrition 0.000 description 1
238000011992 High performance liquid chromatography with tandem mass spectrometry Methods 0.000 description 1
102000000543 Histamine Receptors Human genes 0.000 description 1
108010002059 Histamine Receptors Proteins 0.000 description 1
101000783617 Homo sapiens 5-hydroxytryptamine receptor 2A Proteins 0.000 description 1
101000761319 Homo sapiens 5-hydroxytryptamine receptor 2B Proteins 0.000 description 1
101100329196 Homo sapiens CYP2D6 gene Proteins 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
208000013016 Hypoglycemia Diseases 0.000 description 1
206010021518 Impaired gastric emptying Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 1
ALFGKMXHOUSVAD-UHFFFAOYSA-N Ketobemidone Chemical compound C=1C=CC(O)=CC=1C1(C(=O)CC)CCN(C)CC1 ALFGKMXHOUSVAD-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
NZDMFGKECODQRY-UHFFFAOYSA-N Maprotiline hydrochloride Chemical compound Cl.C12=CC=CC=C2C2(CCCNC)C3=CC=CC=C3C1CC2 NZDMFGKECODQRY-UHFFFAOYSA-N 0.000 description 1
SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 description 1
208000026139 Memory disease Diseases 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000016257 Mentha pulegium Nutrition 0.000 description 1
235000004357 Mentha x piperita Nutrition 0.000 description 1
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
206010027603 Migraine headaches Diseases 0.000 description 1
101800002372 Motilin Proteins 0.000 description 1
102000002419 Motilin Human genes 0.000 description 1
241000238367 Mya arenaria Species 0.000 description 1
IDBPHNDTYPBSNI-UHFFFAOYSA-N N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide Chemical compound C1CN(CCN2C(N(CC)N=N2)=O)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 IDBPHNDTYPBSNI-UHFFFAOYSA-N 0.000 description 1
HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 1
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
208000012902 Nervous system disease Diseases 0.000 description 1
208000025966 Neurological disease Diseases 0.000 description 1
108090000189 Neuropeptides Proteins 0.000 description 1
206010029412 Nightmare Diseases 0.000 description 1
102000008092 Norepinephrine Plasma Membrane Transport Proteins Human genes 0.000 description 1
108010049586 Norepinephrine Plasma Membrane Transport Proteins Proteins 0.000 description 1
239000008896 Opium Substances 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 description 1
206010033664 Panic attack Diseases 0.000 description 1
208000027089 Parkinsonian disease Diseases 0.000 description 1
206010034010 Parkinsonism Diseases 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
RXBKMJIPNDOHFR-UHFFFAOYSA-N Phenelzine sulfate Chemical compound OS(O)(=O)=O.NNCCC1=CC=CC=C1 RXBKMJIPNDOHFR-UHFFFAOYSA-N 0.000 description 1
CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
229920005372 Plexiglas® Polymers 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
241000288906 Primates Species 0.000 description 1
KXEMQEGRZWUKJS-UHFFFAOYSA-N Raufloridine Natural products COC1=CC=C2C(CCN3CC4C(C)OC=C(C4CC33)C(=O)OC)=C3NC2=C1 KXEMQEGRZWUKJS-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
MEFKEPWMEQBLKI-AIRLBKTGSA-N S-adenosyl-L-methioninate Chemical compound O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H](N)C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-N 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
208000027520 Somatoform disease Diseases 0.000 description 1
208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
101710164184 Synaptic vesicular amine transporter Proteins 0.000 description 1
102100034333 Synaptic vesicular amine transporter Human genes 0.000 description 1
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
208000000323 Tourette Syndrome Diseases 0.000 description 1
208000016620 Tourette disease Diseases 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
208000016599 Uterine disease Diseases 0.000 description 1
206010047139 Vasoconstriction Diseases 0.000 description 1
206010047163 Vasospasm Diseases 0.000 description 1
206010048010 Withdrawal syndrome Diseases 0.000 description 1
BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 description 1
VRFSMNHWWDKGQG-UHFFFAOYSA-M [O-]C(O)=O.OC(O)=O.N.[Cs+] Chemical compound [O-]C(O)=O.OC(O)=O.N.[Cs+] VRFSMNHWWDKGQG-UHFFFAOYSA-M 0.000 description 1
XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 1
210000001015 abdomen Anatomy 0.000 description 1
230000001594 aberrant effect Effects 0.000 description 1
229960004892 acemetacin Drugs 0.000 description 1
FSQKKOOTNAMONP-UHFFFAOYSA-N acemetacin Chemical compound CC1=C(CC(=O)OCC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 FSQKKOOTNAMONP-UHFFFAOYSA-N 0.000 description 1
102000034337 acetylcholine receptors Human genes 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
229960001570 ademetionine Drugs 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
229960002629 agomelatine Drugs 0.000 description 1
YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 description 1
239000000556 agonist Substances 0.000 description 1
201000007930 alcohol dependence Diseases 0.000 description 1
229960001391 alfentanil Drugs 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000007815 allergy Effects 0.000 description 1
KGYFOSCXVAXULR-UHFFFAOYSA-N allylprodine Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CCN(C)CC1CC=C KGYFOSCXVAXULR-UHFFFAOYSA-N 0.000 description 1
229950004361 allylprodine Drugs 0.000 description 1
UVAZQQHAVMNMHE-XJKSGUPXSA-N alphaprodine Chemical compound C=1C=CC=CC=1[C@@]1(OC(=O)CC)CCN(C)C[C@@H]1C UVAZQQHAVMNMHE-XJKSGUPXSA-N 0.000 description 1
229960001349 alphaprodine Drugs 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
LKYQLAWMNBFNJT-UHFFFAOYSA-N anileridine Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCC1=CC=C(N)C=C1 LKYQLAWMNBFNJT-UHFFFAOYSA-N 0.000 description 1
229960002512 anileridine Drugs 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
239000003416 antiarrhythmic agent Substances 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
239000003420 antiserotonin agent Substances 0.000 description 1
229940124584 antitussives Drugs 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
229940005530 anxiolytics Drugs 0.000 description 1
230000036528 appetite Effects 0.000 description 1
235000019789 appetite Nutrition 0.000 description 1
229960004372 aripiprazole Drugs 0.000 description 1
239000003693 atypical antipsychotic agent Substances 0.000 description 1
229940127236 atypical antipsychotics Drugs 0.000 description 1
239000011324 bead Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
RDJGWRFTDZZXSM-RNWLQCGYSA-N benzylmorphine Chemical compound O([C@@H]1[C@]23CCN([C@H](C4)[C@@H]3C=C[C@@H]1O)C)C1=C2C4=CC=C1OCC1=CC=CC=C1 RDJGWRFTDZZXSM-RNWLQCGYSA-N 0.000 description 1
239000002876 beta blocker Substances 0.000 description 1
229940097320 beta blocking agent Drugs 0.000 description 1
BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 1
FLKWNFFCSSJANB-UHFFFAOYSA-N bezitramide Chemical compound O=C1N(C(=O)CC)C2=CC=CC=C2N1C(CC1)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 FLKWNFFCSSJANB-UHFFFAOYSA-N 0.000 description 1
229960004611 bezitramide Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
208000028683 bipolar I disease Diseases 0.000 description 1
230000037396 body weight Effects 0.000 description 1
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
229950003872 bucolome Drugs 0.000 description 1
RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 description 1
229960001736 buprenorphine Drugs 0.000 description 1
IFKLAQQSCNILHL-QHAWAJNXSA-N butorphanol Chemical compound N1([C@@H]2CC3=CC=C(C=C3[C@@]3([C@]2(CCCC3)O)CC1)O)CC1CCC1 IFKLAQQSCNILHL-QHAWAJNXSA-N 0.000 description 1
229960001113 butorphanol Drugs 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
235000009120 camo Nutrition 0.000 description 1
229950011318 cannabidiol Drugs 0.000 description 1
QHMBSVQNZZTUGM-ZWKOTPCHSA-N cannabidiol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-ZWKOTPCHSA-N 0.000 description 1
ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 description 1
231100000259 cardiotoxicity Toxicity 0.000 description 1
230000007681 cardiovascular toxicity Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
238000000423 cell based assay Methods 0.000 description 1
208000015114 central nervous system disease Diseases 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
235000005607 chanvre indien Nutrition 0.000 description 1
235000019693 cherries Nutrition 0.000 description 1
229960004782 chlordiazepoxide Drugs 0.000 description 1
ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 1
229960003291 chlorphenamine Drugs 0.000 description 1
210000002987 choroid plexus Anatomy 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
230000002060 circadian Effects 0.000 description 1
229950010886 clidanac Drugs 0.000 description 1
229960004170 clozapine Drugs 0.000 description 1
QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 1
238000011260 co-administration Methods 0.000 description 1
230000001149 cognitive effect Effects 0.000 description 1
229940125846 compound 25 Drugs 0.000 description 1
238000004590 computer program Methods 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
201000011634 coronary artery vasospasm Diseases 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
229940111134 coxibs Drugs 0.000 description 1
XBRXTUGRUXGBPX-DLBZAZTESA-N cyclazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N([C@@H]1CCCC[C@@H]11)CCN1C(=O)C1=CC=CO1 XBRXTUGRUXGBPX-DLBZAZTESA-N 0.000 description 1
239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000002950 deficient Effects 0.000 description 1
230000006735 deficit Effects 0.000 description 1
CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 1
230000017858 demethylation Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
229960003914 desipramine Drugs 0.000 description 1
LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 description 1
229950003851 desomorphine Drugs 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
WDEFBBTXULIOBB-WBVHZDCISA-N dextilidine Chemical compound C=1C=CC=CC=1[C@@]1(C(=O)OCC)CCC=C[C@H]1N(C)C WDEFBBTXULIOBB-WBVHZDCISA-N 0.000 description 1
JAQUASYNZVUNQP-PVAVHDDUSA-N dextrorphan Chemical compound C1C2=CC=C(O)C=C2[C@@]23CCN(C)[C@@H]1[C@H]2CCCC3 JAQUASYNZVUNQP-PVAVHDDUSA-N 0.000 description 1
229950006878 dextrorphan Drugs 0.000 description 1
RXTHKWVSXOIHJS-UHFFFAOYSA-N diampromide Chemical compound C=1C=CC=CC=1N(C(=O)CC)CC(C)N(C)CCC1=CC=CC=C1 RXTHKWVSXOIHJS-UHFFFAOYSA-N 0.000 description 1
229950001059 diampromide Drugs 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
230000029087 digestion Effects 0.000 description 1
PCXRACLQFPRCBB-ZWKOTPCHSA-N dihydrocannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)C)CCC(C)=C1 PCXRACLQFPRCBB-ZWKOTPCHSA-N 0.000 description 1
UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
RHUWRJWFHUKVED-UHFFFAOYSA-N dimenoxadol Chemical compound C=1C=CC=CC=1C(C(=O)OCCN(C)C)(OCC)C1=CC=CC=C1 RHUWRJWFHUKVED-UHFFFAOYSA-N 0.000 description 1
229950011187 dimenoxadol Drugs 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000009509 drug development Methods 0.000 description 1
239000003596 drug target Substances 0.000 description 1
230000008406 drug-drug interaction Effects 0.000 description 1
239000000975 dye Substances 0.000 description 1
235000005686 eating Nutrition 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
229960004756 ethanol Drugs 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
MORSAEFGQPDBKM-UHFFFAOYSA-N ethylmethylthiambutene Chemical compound C=1C=CSC=1C(=CC(C)N(C)CC)C1=CC=CS1 MORSAEFGQPDBKM-UHFFFAOYSA-N 0.000 description 1
229950006111 ethylmethylthiambutene Drugs 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000005284 excitation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
229960001395 fenbufen Drugs 0.000 description 1
ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 description 1
229950006236 fenclofenac Drugs 0.000 description 1
IDKAXRLETRCXKS-UHFFFAOYSA-N fenclofenac Chemical compound OC(=O)CC1=CC=CC=C1OC1=CC=C(Cl)C=C1Cl IDKAXRLETRCXKS-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
206010016766 flatulence Diseases 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229960002464 fluoxetine Drugs 0.000 description 1
229960004038 fluvoxamine Drugs 0.000 description 1
CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 1
230000004907 flux Effects 0.000 description 1
230000037406 food intake Effects 0.000 description 1
235000012631 food intake Nutrition 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
238000002825 functional assay Methods 0.000 description 1
230000004927 fusion Effects 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
208000001288 gastroparesis Diseases 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000003193 general anesthetic agent Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229960004410 glucametacin Drugs 0.000 description 1
229960002389 glycol salicylate Drugs 0.000 description 1
QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
239000000380 hallucinogen Substances 0.000 description 1
229960003878 haloperidol Drugs 0.000 description 1
230000036541 health Effects 0.000 description 1
239000011487 hemp Substances 0.000 description 1
NSILVESQCSUIAJ-UHFFFAOYSA-M hexocyclium methyl sulfate Chemical compound COS([O-])(=O)=O.C1C[N+](C)(C)CCN1CC(O)(C=1C=CC=CC=1)C1CCCCC1 NSILVESQCSUIAJ-UHFFFAOYSA-M 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
235000001050 hortel pimenta Nutrition 0.000 description 1
WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 description 1
229960001410 hydromorphone Drugs 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
208000031424 hyperprolactinemia Diseases 0.000 description 1
230000009610 hypersensitivity Effects 0.000 description 1
239000003326 hypnotic agent Substances 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
230000002267 hypothalamic effect Effects 0.000 description 1
230000002631 hypothermal effect Effects 0.000 description 1
229960002595 ibuproxam Drugs 0.000 description 1
BYPIURIATSUHDW-UHFFFAOYSA-N ibuproxam Chemical compound CC(C)CC1=CC=C(C(C)C(=O)NO)C=C1 BYPIURIATSUHDW-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229960004801 imipramine Drugs 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
239000007972 injectable composition Substances 0.000 description 1
208000003243 intestinal obstruction Diseases 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
208000023589 ischemic disease Diseases 0.000 description 1
229960002672 isocarboxazid Drugs 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
YYUAYBYLJSNDCX-UHFFFAOYSA-N isoxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC=1C=C(C)ON=1 YYUAYBYLJSNDCX-UHFFFAOYSA-N 0.000 description 1
229950002252 isoxicam Drugs 0.000 description 1
229960005417 ketanserin Drugs 0.000 description 1
229960003029 ketobemidone Drugs 0.000 description 1
229960004752 ketorolac Drugs 0.000 description 1
OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000013016 learning Effects 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
229950010274 lofentanil Drugs 0.000 description 1
IMYHGORQCPYVBZ-NLFFAJNJSA-N lofentanil Chemical compound CCC(=O)N([C@@]1([C@@H](CN(CCC=2C=CC=CC=2)CC1)C)C(=O)OC)C1=CC=CC=C1 IMYHGORQCPYVBZ-NLFFAJNJSA-N 0.000 description 1
229960001571 loperamide Drugs 0.000 description 1
RDOIQAHITMMDAJ-UHFFFAOYSA-N loperamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N(C)C)CCN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 RDOIQAHITMMDAJ-UHFFFAOYSA-N 0.000 description 1
210000003141 lower extremity Anatomy 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000004020 luminiscence type Methods 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
206010025482 malaise Diseases 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
229960003803 meclofenamic acid Drugs 0.000 description 1
KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
229960004963 mesalazine Drugs 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
YEOTYALSMRNXLJ-UHFFFAOYSA-N metazosin Chemical compound C1CN(C(=O)C(C)OC)CCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 YEOTYALSMRNXLJ-UHFFFAOYSA-N 0.000 description 1
229960001797 methadone Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 description 1
239000012569 microbial contaminant Substances 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
230000003228 microsomal effect Effects 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229960001785 mirtazapine Drugs 0.000 description 1
RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229960005285 mofebutazone Drugs 0.000 description 1
REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical compound O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
210000002464 muscle smooth vascular Anatomy 0.000 description 1
HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 description 1
229960000951 mycophenolic acid Drugs 0.000 description 1
229960000805 nalbuphine Drugs 0.000 description 1
NETZHAKZCGBWSS-CEDHKZHLSA-N nalbuphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]1(O)CC[C@@H]3O)CN2CC1CCC1 NETZHAKZCGBWSS-CEDHKZHLSA-N 0.000 description 1
CVRCFLFEGNKMEC-UHFFFAOYSA-N naphthalen-1-yl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC2=CC=CC=C12 CVRCFLFEGNKMEC-UHFFFAOYSA-N 0.000 description 1
229960002009 naproxen Drugs 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
229960001800 nefazodone Drugs 0.000 description 1
VRBKIVRKKCLPHA-UHFFFAOYSA-N nefazodone Chemical compound O=C1N(CCOC=2C=CC=CC=2)C(CC)=NN1CCCN(CC1)CCN1C1=CC=CC(Cl)=C1 VRBKIVRKKCLPHA-UHFFFAOYSA-N 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
229960004300 nicomorphine Drugs 0.000 description 1
HNDXBGYRMHRUFN-CIVUWBIHSA-N nicomorphine Chemical compound O([C@H]1C=C[C@H]2[C@H]3CC=4C5=C(C(=CC=4)OC(=O)C=4C=NC=CC=4)O[C@@H]1[C@]52CCN3C)C(=O)C1=CC=CN=C1 HNDXBGYRMHRUFN-CIVUWBIHSA-N 0.000 description 1
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
229960000965 nimesulide Drugs 0.000 description 1
HYWYRSMBCFDLJT-UHFFFAOYSA-N nimesulide Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1=CC=CC=C1 HYWYRSMBCFDLJT-UHFFFAOYSA-N 0.000 description 1
230000000422 nocturnal effect Effects 0.000 description 1
229940121367 non-opioid analgesics Drugs 0.000 description 1
239000002767 noradrenalin uptake inhibitor Substances 0.000 description 1
230000000966 norepinephrine reuptake Effects 0.000 description 1
229960004013 normethadone Drugs 0.000 description 1
WCJFBSYALHQBSK-UHFFFAOYSA-N normethadone Chemical compound C=1C=CC=CC=1C(CCN(C)C)(C(=O)CC)C1=CC=CC=C1 WCJFBSYALHQBSK-UHFFFAOYSA-N 0.000 description 1
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
229960005017 olanzapine Drugs 0.000 description 1
KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
QQBDLJCYGRGAKP-FOCLMDBBSA-N olsalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=C(C(O)=CC=2)C(O)=O)=C1 QQBDLJCYGRGAKP-FOCLMDBBSA-N 0.000 description 1
229960004110 olsalazine Drugs 0.000 description 1
229960000381 omeprazole Drugs 0.000 description 1
229940127240 opiate Drugs 0.000 description 1
229960001027 opium Drugs 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000007935 oral tablet Substances 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000008520 organization Effects 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
229960000273 oxametacin Drugs 0.000 description 1
AJRNYCDWNITGHF-UHFFFAOYSA-N oxametacin Chemical compound CC1=C(CC(=O)NO)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 AJRNYCDWNITGHF-UHFFFAOYSA-N 0.000 description 1
229960002739 oxaprozin Drugs 0.000 description 1
OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 description 1
150000007978 oxazole derivatives Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229960005118 oxymorphone Drugs 0.000 description 1
229960000649 oxyphenbutazone Drugs 0.000 description 1
HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
229960001057 paliperidone Drugs 0.000 description 1
229960003294 papaveretum Drugs 0.000 description 1
208000011906 peptic ulcer disease Diseases 0.000 description 1
230000008447 perception Effects 0.000 description 1
229960000482 pethidine Drugs 0.000 description 1
238000009522 phase III clinical trial Methods 0.000 description 1
LOXCOAXRHYDLOW-UHFFFAOYSA-N phenadoxone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)CC)CC(C)N1CCOCC1 LOXCOAXRHYDLOW-UHFFFAOYSA-N 0.000 description 1
229950004540 phenadoxone Drugs 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
229960002695 phenobarbital Drugs 0.000 description 1
229960003742 phenol Drugs 0.000 description 1
150000007965 phenolic acids Chemical class 0.000 description 1
CFBQYWXPZVQQTN-QPTUXGOLSA-N phenomorphan Chemical compound C([C@]12CCCC[C@H]1[C@H]1CC3=CC=C(C=C32)O)CN1CCC1=CC=CC=C1 CFBQYWXPZVQQTN-QPTUXGOLSA-N 0.000 description 1
229950011496 phenomorphan Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
229960001802 phenylephrine Drugs 0.000 description 1
DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 1
229960000395 phenylpropanolamine Drugs 0.000 description 1
229960002036 phenytoin Drugs 0.000 description 1
FIADGNVRKBPQEU-UHFFFAOYSA-N pizotifen Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CCC2=C1C=CS2 FIADGNVRKBPQEU-UHFFFAOYSA-N 0.000 description 1
229960004572 pizotifen Drugs 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
235000020004 porter Nutrition 0.000 description 1
239000008057 potassium phosphate buffer Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
201000009395 primary hyperaldosteronism Diseases 0.000 description 1
229960000825 proglumetacin Drugs 0.000 description 1
PTXGHCGBYMQQIG-UHFFFAOYSA-N proglumetacin Chemical compound C=1C=CC=CC=1C(=O)NC(C(=O)N(CCC)CCC)CCC(=O)OCCCN(CC1)CCN1CCOC(=O)CC(C1=CC(OC)=CC=C11)=C(C)N1C(=O)C1=CC=C(Cl)C=C1 PTXGHCGBYMQQIG-UHFFFAOYSA-N 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
229960005385 proguanil Drugs 0.000 description 1
XJKQCILVUHXVIQ-UHFFFAOYSA-N properidine Chemical compound C=1C=CC=CC=1C1(C(=O)OC(C)C)CCN(C)CC1 XJKQCILVUHXVIQ-UHFFFAOYSA-N 0.000 description 1
229950004345 properidine Drugs 0.000 description 1
ZBAFFZBKCMWUHM-UHFFFAOYSA-N propiram Chemical compound C=1C=CC=NC=1N(C(=O)CC)C(C)CN1CCCCC1 ZBAFFZBKCMWUHM-UHFFFAOYSA-N 0.000 description 1
229950003779 propiram Drugs 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229960002466 proquazone Drugs 0.000 description 1
JTIGKVIOEQASGT-UHFFFAOYSA-N proquazone Chemical compound N=1C(=O)N(C(C)C)C2=CC(C)=CC=C2C=1C1=CC=CC=C1 JTIGKVIOEQASGT-UHFFFAOYSA-N 0.000 description 1
230000006920 protein precipitation Effects 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
238000003908 quality control method Methods 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
230000036385 rapid eye movement (rem) sleep Effects 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
229960001534 risperidone Drugs 0.000 description 1
RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
150000003872 salicylic acid derivatives Chemical class 0.000 description 1
230000000698 schizophrenic effect Effects 0.000 description 1
238000012216 screening Methods 0.000 description 1
230000028327 secretion Effects 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
230000001953 sensory effect Effects 0.000 description 1
239000003244 serotonin 2B agonist Substances 0.000 description 1
GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
230000035939 shock Effects 0.000 description 1
230000016160 smooth muscle contraction Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
230000000392 somatic effect Effects 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
208000020431 spinal cord injury Diseases 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
229960004739 sufentanil Drugs 0.000 description 1
GGCSSNBKKAUURC-UHFFFAOYSA-N sufentanil Chemical group C1CN(CCC=2SC=CC=2)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 GGCSSNBKKAUURC-UHFFFAOYSA-N 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
229960001940 sulfasalazine Drugs 0.000 description 1
NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
229960000894 sulindac Drugs 0.000 description 1
MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
210000002820 sympathetic nervous system Anatomy 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
229960001402 tilidine Drugs 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
229960005371 tolbutamide Drugs 0.000 description 1
229960001017 tolmetin Drugs 0.000 description 1
UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
OOGJQPCLVADCPB-HXUWFJFHSA-N tolterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-HXUWFJFHSA-N 0.000 description 1
229960004045 tolterodine Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
230000009898 traumatic memory Effects 0.000 description 1
229960003991 trazodone Drugs 0.000 description 1
PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
FYZXEMANQYHCFX-UHFFFAOYSA-K tripotassium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxymethyl)amino]acetate Chemical compound [K+].[K+].[K+].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O FYZXEMANQYHCFX-UHFFFAOYSA-K 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
210000001364 upper extremity Anatomy 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
230000025033 vasoconstriction Effects 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
229960005080 warfarin Drugs 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
229960000317 yohimbine Drugs 0.000 description 1
AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
229960000607 ziprasidone Drugs 0.000 description 1
MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1