JP2010504367A - 性機能障害、認知障害、精神病性障害、不安、鬱病などを処置するための５ｈｔ１ａ受容体モジュレーターとしての５−｛２−［４−（２−メチル−５−キノリニル）−ｌ−ピペリジニル］エチル｝キノリノン誘導体 - Google Patents

Info

Publication number

JP2010504367A

JP2010504367A JP2009529679A JP2009529679A JP2010504367A JP 2010504367 A JP2010504367 A JP 2010504367A JP 2009529679 A JP2009529679 A JP 2009529679A JP 2009529679 A JP2009529679 A JP 2009529679A JP 2010504367 A JP2010504367 A JP 2010504367A

Authority

JP

Japan

Prior art keywords

compound

methyl

alkyl

ethyl

quinolinyl

Prior art date

2006-09-26

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

Links

• Espacenet
• Global Dossier
• Discuss

• -1 2-methyl-5-quinolinyl Chemical group 0.000 title claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims description 7
• 208000019901 Anxiety disease Diseases 0.000 title description 16
• 208000028017 Psychotic disease Diseases 0.000 title description 15
• 208000010877 cognitive disease Diseases 0.000 title description 15
• 208000028698 Cognitive impairment Diseases 0.000 title description 13
• 201000001880 Sexual dysfunction Diseases 0.000 title description 8
• 231100000872 sexual dysfunction Toxicity 0.000 title description 8
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title description 6
• 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 title 1
• 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 title 1
• 230000036506 anxiety Effects 0.000 title 1
• 229940075993 receptor modulator Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 200
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 57
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
• 239000001257 hydrogen Substances 0.000 claims abstract description 28
• 125000005843 halogen group Chemical group 0.000 claims abstract description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
• 125000004429 atom Chemical group 0.000 claims abstract description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 6
• 125000001475 halogen functional group Chemical group 0.000 claims abstract description 4
• 229940125904 compound 1 Drugs 0.000 claims description 11
• 150000003839 salts Chemical class 0.000 claims description 11
• 150000002431 hydrogen Chemical class 0.000 claims description 9
• PDLXDQOODGXTSQ-UHFFFAOYSA-N 1,6-dimethyl-5-[2-[4-(2-methylquinolin-5-yl)piperazin-1-yl]ethyl]-3,4-dihydroquinolin-2-one Chemical compound CC1=CC=C2C(N3CCN(CC3)CCC3=C4CCC(=O)N(C4=CC=C3C)C)=CC=CC2=N1 PDLXDQOODGXTSQ-UHFFFAOYSA-N 0.000 claims description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
• 229940126639 Compound 33 Drugs 0.000 claims description 5
• PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 claims description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims description 5
• GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 5
• BZFUYHDDVGBTOS-UHFFFAOYSA-N 6-methyl-5-[2-[4-(2-methylquinolin-5-yl)piperazin-1-yl]ethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C1C=CC(C)=C2CCN(CC1)CCN1C1=CC=CC2=NC(C)=CC=C21 BZFUYHDDVGBTOS-UHFFFAOYSA-N 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 229910052757 nitrogen Inorganic materials 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims description 2
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims description 2
• UUWQIBYZFVEIMA-NRFANRHFSA-N 1,6-dimethyl-5-[2-[(2s)-2-methyl-4-(2-methylquinolin-5-yl)piperazin-1-yl]ethyl]quinolin-2-one Chemical compound CC1=CC=C2C(N3C[C@@H](N(CC3)CCC=3C=4C=CC(=O)N(C)C=4C=CC=3C)C)=CC=CC2=N1 UUWQIBYZFVEIMA-NRFANRHFSA-N 0.000 claims description 2
• ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims description 2
• XDDBLROZRANMSE-XOYNAWAESA-N 3,6-dimethyl-7-[2-[(2s)-2-methyl-4-(2-methylquinolin-5-yl)piperazin-1-yl]ethyl]-1a,7b-dihydro-1h-cyclopropa[c]quinolin-2-one Chemical compound CC1=CC=C2C(N3C[C@@H](N(CC3)CCC=3C=4C5CC5C(=O)N(C)C=4C=CC=3C)C)=CC=CC2=N1 XDDBLROZRANMSE-XOYNAWAESA-N 0.000 claims description 2
• XBOCLCGHZJWWCY-FQEVSTJZSA-N 5-[2-[(2s)-4-(7-fluoro-2-methylquinolin-5-yl)-2-methylpiperazin-1-yl]ethyl]-1,6-dimethylquinolin-2-one Chemical compound CC1=CC=C2C(N3C[C@@H](N(CC3)CCC=3C=4C=CC(=O)N(C)C=4C=CC=3C)C)=CC(F)=CC2=N1 XBOCLCGHZJWWCY-FQEVSTJZSA-N 0.000 claims description 2
• LDPZTEPHJATCEM-IBGZPJMESA-N 5-[2-[(2s)-4-(7-fluoro-2-methylquinolin-5-yl)-2-methylpiperazin-1-yl]ethyl]-6-methyl-3,4-dihydro-1h-quinolin-2-one Chemical compound CC1=CC=C2C(N3C[C@@H](N(CC3)CCC=3C=4CCC(=O)NC=4C=CC=3C)C)=CC(F)=CC2=N1 LDPZTEPHJATCEM-IBGZPJMESA-N 0.000 claims description 2
• HRWBYOOBXRZGGR-UHFFFAOYSA-N 5-[2-[4-(7-fluoro-2-methylquinolin-5-yl)piperazin-1-yl]ethyl]-1,6-dimethylquinolin-2-one Chemical compound CN1C(=O)C=CC2=C1C=CC(C)=C2CCN(CC1)CCN1C1=CC(F)=CC2=NC(C)=CC=C21 HRWBYOOBXRZGGR-UHFFFAOYSA-N 0.000 claims description 2
• GOTWNFPSUDVYGZ-UHFFFAOYSA-N 5-[2-[4-(7-fluoro-2-methylquinolin-5-yl)piperazin-1-yl]ethyl]-6-methyl-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C1C=CC(C)=C2CCN(CC1)CCN1C1=CC(F)=CC2=NC(C)=CC=C21 GOTWNFPSUDVYGZ-UHFFFAOYSA-N 0.000 claims description 2
• WJEBTWQLGLLSGW-UHFFFAOYSA-N 6-methyl-5-[2-[4-(2-methylquinolin-5-yl)piperazin-1-yl]ethyl]-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C1C=CC(C)=C2CCN(CC1)CCN1C1=CC=CC2=NC(C)=CC=C21 WJEBTWQLGLLSGW-UHFFFAOYSA-N 0.000 claims description 2
• WYKBJZPYLVTTKC-UHFFFAOYSA-N 6-methyl-5-[2-[4-(2-methylquinolin-5-yl)piperidin-1-yl]ethyl]-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C1C=CC(C)=C2CCN(CC1)CCC1C1=CC=CC2=NC(C)=CC=C21 WYKBJZPYLVTTKC-UHFFFAOYSA-N 0.000 claims description 2
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
• 239000005977 Ethylene Substances 0.000 claims description 2
• OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 claims description 2
• KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 claims description 2
• 229940126543 compound 14 Drugs 0.000 claims description 2
• 229940125758 compound 15 Drugs 0.000 claims description 2
• 229940126142 compound 16 Drugs 0.000 claims description 2
• 229940125782 compound 2 Drugs 0.000 claims description 2
• 229940126086 compound 21 Drugs 0.000 claims description 2
• 229940125833 compound 23 Drugs 0.000 claims description 2
• GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
• 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
• 239000000543 intermediate Substances 0.000 description 66
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 48
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 46
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
• 208000035475 disorder Diseases 0.000 description 36
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
• 238000000034 method Methods 0.000 description 29
• 238000006243 chemical reaction Methods 0.000 description 27
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
• 239000000203 mixture Substances 0.000 description 25
• 239000000243 solution Substances 0.000 description 25
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
• 239000012458 free base Substances 0.000 description 21
• 238000001819 mass spectrum Methods 0.000 description 21
• 239000000546 pharmaceutical excipient Substances 0.000 description 20
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
• 238000003556 assay Methods 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
• 239000002249 anxiolytic agent Substances 0.000 description 17
• 108020003175 receptors Proteins 0.000 description 17
• 102000005962 receptors Human genes 0.000 description 17
• 230000000949 anxiolytic effect Effects 0.000 description 16
• 238000002360 preparation method Methods 0.000 description 16
• 239000000126 substance Substances 0.000 description 16
• 230000000147 hypnotic effect Effects 0.000 description 15
• 239000008194 pharmaceutical composition Substances 0.000 description 15
• 239000011541 reaction mixture Substances 0.000 description 15
• 239000000932 sedative agent Substances 0.000 description 15
• 208000019116 sleep disease Diseases 0.000 description 15
• 208000019022 Mood disease Diseases 0.000 description 13
• 239000011734 sodium Substances 0.000 description 13
• 206010012218 Delirium Diseases 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• 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 12
• 239000012043 crude product Substances 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• 238000005481 NMR spectroscopy Methods 0.000 description 11
• 238000005160 1H NMR spectroscopy Methods 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 10
• 210000004027 cell Anatomy 0.000 description 10
• 201000010099 disease Diseases 0.000 description 10
• 230000001624 sedative effect Effects 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• 239000000380 hallucinogen Substances 0.000 description 9
• 238000004519 manufacturing process Methods 0.000 description 9
• 230000002085 persistent effect Effects 0.000 description 9
• 208000022821 personality disease Diseases 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• 239000002904 solvent Substances 0.000 description 9
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 8
• 206010012289 Dementia Diseases 0.000 description 8
• 239000007983 Tris buffer Substances 0.000 description 8
• 229940025084 amphetamine Drugs 0.000 description 8
• 239000003814 drug Substances 0.000 description 8
• 239000012528 membrane Substances 0.000 description 8
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• 239000012044 organic layer Substances 0.000 description 7
• 229940002612 prodrug Drugs 0.000 description 7
• 239000000651 prodrug Substances 0.000 description 7
• 208000020016 psychiatric disease Diseases 0.000 description 7
• 238000006268 reductive amination reaction Methods 0.000 description 7
• 238000002821 scintillation proximity assay Methods 0.000 description 7
• 208000011117 substance-related disease Diseases 0.000 description 7
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 7
• WSEQXVZVJXJVFP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WSEQXVZVJXJVFP-UHFFFAOYSA-N 0.000 description 6
• 208000022497 Cocaine-Related disease Diseases 0.000 description 6
• 208000026251 Opioid-Related disease Diseases 0.000 description 6
• 208000005374 Poisoning Diseases 0.000 description 6
• 239000012131 assay buffer Substances 0.000 description 6
• 239000000872 buffer Substances 0.000 description 6
• 229960003920 cocaine Drugs 0.000 description 6
• 239000002552 dosage form Substances 0.000 description 6
• 229940079593 drug Drugs 0.000 description 6
• 230000004064 dysfunction Effects 0.000 description 6
• 230000014759 maintenance of location Effects 0.000 description 6
• 239000003607 modifier Substances 0.000 description 6
• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 6
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
• 231100000572 poisoning Toxicity 0.000 description 6
• 230000000607 poisoning effect Effects 0.000 description 6
• 238000000159 protein binding assay Methods 0.000 description 6
• 229920006395 saturated elastomer Polymers 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• 208000031091 Amnestic disease Diseases 0.000 description 5
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
• 206010013654 Drug abuse Diseases 0.000 description 5
• 101000631929 Homo sapiens Sodium-dependent serotonin transporter Proteins 0.000 description 5
• LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 5
• 238000007792 addition Methods 0.000 description 5
• 239000000935 antidepressant agent Substances 0.000 description 5
• 229940005513 antidepressants Drugs 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• 229960001948 caffeine Drugs 0.000 description 5
• VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 5
• 238000003818 flash chromatography Methods 0.000 description 5
• 239000003326 hypnotic agent Substances 0.000 description 5
• JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 5
• 229950010883 phencyclidine Drugs 0.000 description 5
• 230000002265 prevention Effects 0.000 description 5
• 229940125723 sedative agent Drugs 0.000 description 5
• 208000020685 sleep-wake disease Diseases 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• SRZAJIYEMAZWPF-UHFFFAOYSA-N 2-(1,6-dimethyl-2-oxo-3,4-dihydroquinolin-5-yl)acetaldehyde Chemical compound CC1=CC=C2N(C)C(=O)CCC2=C1CC=O SRZAJIYEMAZWPF-UHFFFAOYSA-N 0.000 description 4
• JWCDUUFOAZFFMX-UHFFFAOYSA-N 2-ethenoxy-n,n-dimethylethanamine Chemical compound CN(C)CCOC=C JWCDUUFOAZFFMX-UHFFFAOYSA-N 0.000 description 4
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
• 208000007848 Alcoholism Diseases 0.000 description 4
• 208000029197 Amphetamine-Related disease Diseases 0.000 description 4
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 4
• 208000020925 Bipolar disease Diseases 0.000 description 4
• 241000218236 Cannabis Species 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• 206010026749 Mania Diseases 0.000 description 4
• 208000003863 Marijuana Abuse Diseases 0.000 description 4
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 4
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 4
• 239000000556 agonist Substances 0.000 description 4
• 239000005557 antagonist Substances 0.000 description 4
• 239000000164 antipsychotic agent Substances 0.000 description 4
• 229940005529 antipsychotics Drugs 0.000 description 4
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 4
• 239000000460 chlorine Substances 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 238000007796 conventional method Methods 0.000 description 4
• 239000006185 dispersion Substances 0.000 description 4
• 206010013663 drug dependence Diseases 0.000 description 4
• IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
• 230000006870 function Effects 0.000 description 4
• 238000004128 high performance liquid chromatography Methods 0.000 description 4
• 102000055801 human SLC6A4 Human genes 0.000 description 4
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
• 230000000155 isotopic effect Effects 0.000 description 4
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
• 208000024714 major depressive disease Diseases 0.000 description 4
• 239000002480 mineral oil Substances 0.000 description 4
• 235000010446 mineral oil Nutrition 0.000 description 4
• 239000006186 oral dosage form Substances 0.000 description 4
• 229910052763 palladium Inorganic materials 0.000 description 4
• 208000007100 phencyclidine abuse Diseases 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 206010036596 premature ejaculation Diseases 0.000 description 4
• 230000002829 reductive effect Effects 0.000 description 4
• 239000011780 sodium chloride Substances 0.000 description 4
• 239000012312 sodium hydride Substances 0.000 description 4
• 229910000104 sodium hydride Inorganic materials 0.000 description 4
• 208000024891 symptom Diseases 0.000 description 4
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 3
• ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 3
• STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 3
• MQBDZZNHXVZHPX-UHFFFAOYSA-N (6-chloro-2-oxo-1h-quinolin-5-yl) trifluoromethanesulfonate Chemical compound N1C(=O)C=CC2=C1C=CC(Cl)=C2OS(=O)(=O)C(F)(F)F MQBDZZNHXVZHPX-UHFFFAOYSA-N 0.000 description 3
• 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 3
• MKCDJVNZNIVWTH-UHFFFAOYSA-N 1,6-dimethyl-5-prop-2-enylquinolin-2-one Chemical compound CN1C(=O)C=CC2=C(CC=C)C(C)=CC=C21 MKCDJVNZNIVWTH-UHFFFAOYSA-N 0.000 description 3
• NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 3
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
• 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 description 3
• 208000000044 Amnesia Diseases 0.000 description 3
• 208000004230 Gender Dysphoria Diseases 0.000 description 3
• 208000029810 Gender identity disease Diseases 0.000 description 3
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 3
• SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 3
• 230000006986 amnesia Effects 0.000 description 3
• 238000004458 analytical method Methods 0.000 description 3
• 229940005530 anxiolytics Drugs 0.000 description 3
• 230000027455 binding Effects 0.000 description 3
• 239000011230 binding agent Substances 0.000 description 3
• 210000004978 chinese hamster ovary cell Anatomy 0.000 description 3
• 238000002983 circular dichroism Methods 0.000 description 3
• 201000006145 cocaine dependence Diseases 0.000 description 3
• 229940125878 compound 36 Drugs 0.000 description 3
• 230000006735 deficit Effects 0.000 description 3
• 239000003085 diluting agent Substances 0.000 description 3
• 239000007884 disintegrant Substances 0.000 description 3
• 235000014632 disordered eating Nutrition 0.000 description 3
• 238000005516 engineering process Methods 0.000 description 3
• 238000001704 evaporation Methods 0.000 description 3
• 239000000945 filler Substances 0.000 description 3
• 238000001914 filtration Methods 0.000 description 3
• 229960002464 fluoxetine Drugs 0.000 description 3
• 230000036541 health Effects 0.000 description 3
• 206010020765 hypersomnia Diseases 0.000 description 3
• 206010022437 insomnia Diseases 0.000 description 3
• 239000000314 lubricant Substances 0.000 description 3
• 239000011777 magnesium Substances 0.000 description 3
• 229960002715 nicotine Drugs 0.000 description 3
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 3
• 239000012285 osmium tetroxide Substances 0.000 description 3
• 229910000489 osmium tetroxide Inorganic materials 0.000 description 3
• 208000019906 panic disease Diseases 0.000 description 3
• 238000002953 preparative HPLC Methods 0.000 description 3
• 201000000980 schizophrenia Diseases 0.000 description 3
• 230000000698 schizophrenic effect Effects 0.000 description 3
• 238000011894 semi-preparative HPLC Methods 0.000 description 3
• 239000003772 serotonin uptake inhibitor Substances 0.000 description 3
• 230000001568 sexual effect Effects 0.000 description 3
• 239000000377 silicon dioxide Substances 0.000 description 3
• 239000012453 solvate Substances 0.000 description 3
• 201000009032 substance abuse Diseases 0.000 description 3
• 238000001665 trituration Methods 0.000 description 3
• 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 2
• SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
• FGFKSBOBRKEBRK-UHFFFAOYSA-N (2-methylquinolin-5-yl) trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC2=NC(C)=CC=C21 FGFKSBOBRKEBRK-UHFFFAOYSA-N 0.000 description 2
• WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 2
• JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
• BUEXSXNHWQJDSA-UHFFFAOYSA-N 2-(1,6-dimethyl-2-oxoquinolin-5-yl)acetaldehyde Chemical compound CN1C(=O)C=CC2=C(CC=O)C(C)=CC=C21 BUEXSXNHWQJDSA-UHFFFAOYSA-N 0.000 description 2
• IYZBWXXLAQGRSL-UHFFFAOYSA-N 2-(6-chloro-1-methyl-2-oxoquinolin-5-yl)acetaldehyde Chemical compound C1=C(Cl)C(CC=O)=C2C=CC(=O)N(C)C2=C1 IYZBWXXLAQGRSL-UHFFFAOYSA-N 0.000 description 2
• XBQMOTAGNJWMQB-UHFFFAOYSA-N 2-(6-methyl-2-oxo-1h-quinolin-5-yl)acetaldehyde Chemical compound N1C(=O)C=CC2=C(CC=O)C(C)=CC=C21 XBQMOTAGNJWMQB-UHFFFAOYSA-N 0.000 description 2
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
• PZNAAXFCMFHGNR-UHFFFAOYSA-N 2-methyl-5-piperazin-1-ylquinoline Chemical compound C=1C=CC2=NC(C)=CC=C2C=1N1CCNCC1 PZNAAXFCMFHGNR-UHFFFAOYSA-N 0.000 description 2
• POSYFQIUELKNKR-UHFFFAOYSA-N 5-bromo-1,6-dimethylquinolin-2-one Chemical compound CN1C(=O)C=CC2=C(Br)C(C)=CC=C21 POSYFQIUELKNKR-UHFFFAOYSA-N 0.000 description 2
• NBROUSPITUKLCY-UHFFFAOYSA-N 5-bromo-6-methyl-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C(Br)C(C)=CC=C21 NBROUSPITUKLCY-UHFFFAOYSA-N 0.000 description 2
• ZISKJANYWYMNSA-UHFFFAOYSA-N 6-chloro-1-methyl-5-prop-2-enylquinolin-2-one Chemical compound C1=C(Cl)C(CC=C)=C2C=CC(=O)N(C)C2=C1 ZISKJANYWYMNSA-UHFFFAOYSA-N 0.000 description 2
• VIGVOBKAAGSKOY-UHFFFAOYSA-N 6-chloro-5-methoxy-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C1C=CC(Cl)=C2OC VIGVOBKAAGSKOY-UHFFFAOYSA-N 0.000 description 2
• GWEKWUIJZUEFER-UHFFFAOYSA-N 6-chloro-5-prop-2-enyl-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C(CC=C)C(Cl)=CC=C21 GWEKWUIJZUEFER-UHFFFAOYSA-N 0.000 description 2
• LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
• 208000008811 Agoraphobia Diseases 0.000 description 2
• 208000024827 Alzheimer disease Diseases 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 208000020706 Autistic disease Diseases 0.000 description 2
• 206010006550 Bulimia nervosa Diseases 0.000 description 2
• 229920002261 Corn starch Polymers 0.000 description 2
• 206010012239 Delusion Diseases 0.000 description 2
• 206010012335 Dependence Diseases 0.000 description 2
• 208000020401 Depressive disease Diseases 0.000 description 2
• 208000007590 Disorders of Excessive Somnolence Diseases 0.000 description 2
• 208000030814 Eating disease Diseases 0.000 description 2
• 208000019454 Feeding and Eating disease Diseases 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 230000005526 G1 to G0 transition Effects 0.000 description 2
• UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 2
• 239000007995 HEPES buffer Substances 0.000 description 2
• 208000004547 Hallucinations Diseases 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
• 206010021030 Hypomania Diseases 0.000 description 2
• 206010057672 Male sexual dysfunction Diseases 0.000 description 2
• 241000124008 Mammalia Species 0.000 description 2
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
• 229920000881 Modified starch Polymers 0.000 description 2
• WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
• 229910002651 NO3 Inorganic materials 0.000 description 2
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
• GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
• 208000006199 Parasomnias Diseases 0.000 description 2
• AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 2
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 229920002873 Polyethylenimine Polymers 0.000 description 2
• 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 description 2
• 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 description 2
• 206010041250 Social phobia Diseases 0.000 description 2
• 229920002472 Starch Polymers 0.000 description 2
• 208000011962 Substance-induced mood disease Diseases 0.000 description 2
• 231100000395 Substance-induced mood disorder Toxicity 0.000 description 2
• 208000011963 Substance-induced psychotic disease Diseases 0.000 description 2
• 231100000393 Substance-induced psychotic disorder Toxicity 0.000 description 2
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 208000028505 alcohol-related disease Diseases 0.000 description 2
• 235000010443 alginic acid Nutrition 0.000 description 2
• 239000000783 alginic acid Substances 0.000 description 2
• 229920000615 alginic acid Polymers 0.000 description 2
• 229960001126 alginic acid Drugs 0.000 description 2
• 150000004781 alginic acids Chemical class 0.000 description 2
• 208000029560 autism spectrum disease Diseases 0.000 description 2
• 239000011324 bead Substances 0.000 description 2
• 230000003542 behavioural effect Effects 0.000 description 2
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 2
• 238000004166 bioassay Methods 0.000 description 2
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
• 229910000024 caesium carbonate Inorganic materials 0.000 description 2
• 201000001843 cannabis dependence Diseases 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• 229910052799 carbon Inorganic materials 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 239000001913 cellulose Substances 0.000 description 2
• 235000010980 cellulose Nutrition 0.000 description 2
• 229920002678 cellulose Polymers 0.000 description 2
• 229960001653 citalopram Drugs 0.000 description 2
• 230000019771 cognition Effects 0.000 description 2
• 229940125877 compound 31 Drugs 0.000 description 2
• 239000008120 corn starch Substances 0.000 description 2
• USRHYDPUVLEVMC-FQEVSTJZSA-N dapoxetine Chemical compound C1([C@H](CCOC=2C3=CC=CC=C3C=CC=2)N(C)C)=CC=CC=C1 USRHYDPUVLEVMC-FQEVSTJZSA-N 0.000 description 2
• 229960005217 dapoxetine Drugs 0.000 description 2
• 230000003412 degenerative effect Effects 0.000 description 2
• 231100000868 delusion Toxicity 0.000 description 2
• 230000001419 dependent effect Effects 0.000 description 2
• 230000003001 depressive effect Effects 0.000 description 2
• 238000013461 design Methods 0.000 description 2
• NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
• ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 2
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
• 239000003136 dopamine receptor stimulating agent Substances 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 239000000284 extract Substances 0.000 description 2
• OJSFTALXCYKKFQ-YLJYHZDGSA-N femoxetine Chemical compound C1=CC(OC)=CC=C1OC[C@@H]1[C@@H](C=2C=CC=CC=2)CCN(C)C1 OJSFTALXCYKKFQ-YLJYHZDGSA-N 0.000 description 2
• 229950003930 femoxetine Drugs 0.000 description 2
• 206010016531 fetishism Diseases 0.000 description 2
• 239000000796 flavoring agent Substances 0.000 description 2
• 229960004038 fluvoxamine Drugs 0.000 description 2
• 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 2
• 235000019253 formic acid Nutrition 0.000 description 2
• 125000000524 functional group Chemical group 0.000 description 2
• ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 description 2
• GVVPGTZRZFNKDS-JXMROGBWSA-N geranyl diphosphate Chemical compound CC(C)=CCC\C(C)=C\CO[P@](O)(=O)OP(O)(O)=O GVVPGTZRZFNKDS-JXMROGBWSA-N 0.000 description 2
• 125000004438 haloalkoxy group Chemical group 0.000 description 2
• 125000001188 haloalkyl group Chemical group 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
• 208000013403 hyperactivity Diseases 0.000 description 2
• 238000011534 incubation Methods 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• 239000003112 inhibitor Substances 0.000 description 2
• 208000014674 injury Diseases 0.000 description 2
• 230000003993 interaction Effects 0.000 description 2
• 210000003734 kidney Anatomy 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
• 206010027175 memory impairment Diseases 0.000 description 2
• TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 2
• 229960004503 metoclopramide Drugs 0.000 description 2
• 229940016286 microcrystalline cellulose Drugs 0.000 description 2
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
• 239000008108 microcrystalline cellulose Substances 0.000 description 2
• 230000036651 mood Effects 0.000 description 2
• 239000004050 mood stabilizer Substances 0.000 description 2
• 229940127237 mood stabilizer Drugs 0.000 description 2
• BNBNYJZSPJVDNQ-UHFFFAOYSA-N n-(4-chloro-2-formyl-3-methoxyphenyl)-2,2-dimethylpropanamide Chemical compound COC1=C(Cl)C=CC(NC(=O)C(C)(C)C)=C1C=O BNBNYJZSPJVDNQ-UHFFFAOYSA-N 0.000 description 2
• MOGZTRMVASFWHB-UHFFFAOYSA-N n-(4-chloro-3-methoxyphenyl)-2,2-dimethylpropanamide Chemical compound COC1=CC(NC(=O)C(C)(C)C)=CC=C1Cl MOGZTRMVASFWHB-UHFFFAOYSA-N 0.000 description 2
• 230000009871 nonspecific binding Effects 0.000 description 2
• 229960002748 norepinephrine Drugs 0.000 description 2
• SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
• 238000002414 normal-phase solid-phase extraction Methods 0.000 description 2
• 210000000056 organ Anatomy 0.000 description 2
• 208000024309 orgasm disease Diseases 0.000 description 2
• 229960002296 paroxetine Drugs 0.000 description 2
• 239000008188 pellet Substances 0.000 description 2
• 230000008447 perception Effects 0.000 description 2
• 239000002953 phosphate buffered saline Substances 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 229920001592 potato starch Polymers 0.000 description 2
• 102000004169 proteins and genes Human genes 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• 229960003770 reboxetine Drugs 0.000 description 2
• 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 2
• 229960002073 sertraline Drugs 0.000 description 2
• VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 2
• BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 description 2
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
• 239000007921 spray Substances 0.000 description 2
• 229940032147 starch Drugs 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• 239000011550 stock solution Substances 0.000 description 2
• 201000006152 substance dependence Diseases 0.000 description 2
• 230000001629 suppression Effects 0.000 description 2
• 239000006188 syrup Substances 0.000 description 2
• 235000020357 syrup Nutrition 0.000 description 2
• 239000003826 tablet Substances 0.000 description 2
• 229960003604 testosterone Drugs 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 230000008733 trauma Effects 0.000 description 2
• YLGRTLMDMVAFNI-UHFFFAOYSA-N tributyl(prop-2-enyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)CC=C YLGRTLMDMVAFNI-UHFFFAOYSA-N 0.000 description 2
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
• VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 2
• MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 2
• 229960000604 valproic acid Drugs 0.000 description 2
• 239000003039 volatile agent Substances 0.000 description 2
• 229960002791 zimeldine Drugs 0.000 description 2
• OYPPVKRFBIWMSX-SXGWCWSVSA-N zimeldine Chemical compound C=1C=CN=CC=1C(=C/CN(C)C)\C1=CC=C(Br)C=C1 OYPPVKRFBIWMSX-SXGWCWSVSA-N 0.000 description 2
• XOFLBQFBSOEHOG-UUOKFMHZSA-N γS-GTP Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=S)[C@@H](O)[C@H]1O XOFLBQFBSOEHOG-UUOKFMHZSA-N 0.000 description 2
• GJJFMKBJSRMPLA-HIFRSBDPSA-N (1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenyl-1-cyclopropanecarboxamide Chemical compound C=1C=CC=CC=1[C@@]1(C(=O)N(CC)CC)C[C@@H]1CN GJJFMKBJSRMPLA-HIFRSBDPSA-N 0.000 description 1
• IGLYMJRIWWIQQE-QUOODJBBSA-N (1S,2R)-2-phenylcyclopropan-1-amine (1R,2S)-2-phenylcyclopropan-1-amine Chemical compound N[C@H]1C[C@@H]1C1=CC=CC=C1.N[C@@H]1C[C@H]1C1=CC=CC=C1 IGLYMJRIWWIQQE-QUOODJBBSA-N 0.000 description 1
• WYDUSKDSKCASEF-LJQANCHMSA-N (1s)-1-cyclohexyl-1-phenyl-3-pyrrolidin-1-ylpropan-1-ol Chemical compound C([C@](O)(C1CCCCC1)C=1C=CC=CC=1)CN1CCCC1 WYDUSKDSKCASEF-LJQANCHMSA-N 0.000 description 1
• JOMNTHCQHJPVAZ-YFKPBYRVSA-N (2s)-2-methylpiperazine Chemical compound C[C@H]1CNCCN1 JOMNTHCQHJPVAZ-YFKPBYRVSA-N 0.000 description 1
• IFNWESYYDINUHV-OLQVQODUSA-N (2s,6r)-2,6-dimethylpiperazine Chemical compound C[C@H]1CNC[C@@H](C)N1 IFNWESYYDINUHV-OLQVQODUSA-N 0.000 description 1
• FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 description 1
• DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 1
• GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 1
• 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 1
• XIGAHNVCEFUYOV-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n-pyridin-2-ylcyclohexanecarboxamide Chemical compound OC(=O)\C=C/C(O)=O.COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCCCC2)C=2N=CC=CC=2)CC1 XIGAHNVCEFUYOV-BTJKTKAUSA-N 0.000 description 1
• DIOHEXPTUTVCNX-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenyl-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 DIOHEXPTUTVCNX-UHFFFAOYSA-N 0.000 description 1
• OQTWHTXLMLMKCA-UHFFFAOYSA-N 1,6-dimethyl-5-[2-[4-(2-methylquinolin-5-yl)piperazin-1-yl]ethyl]-3,4-dihydroquinolin-2-one;dihydrochloride Chemical compound Cl.Cl.CC1=CC=C2C(N3CCN(CC3)CCC3=C4CCC(=O)N(C4=CC=C3C)C)=CC=CC2=N1 OQTWHTXLMLMKCA-UHFFFAOYSA-N 0.000 description 1
• BHUMVBWYOJQMHQ-UHFFFAOYSA-N 1,6-dimethyl-5-[2-[4-(2-methylquinolin-5-yl)piperidin-1-yl]ethyl]-3,4-dihydroquinolin-2-one;dihydrochloride Chemical compound Cl.Cl.CC1=CC=C2C(C3CCN(CC3)CCC3=C(C)C=CC4=C3CCC(=O)N4C)=CC=CC2=N1 BHUMVBWYOJQMHQ-UHFFFAOYSA-N 0.000 description 1
• BBJGFWURZYLXTC-UHFFFAOYSA-N 1,6-dimethyl-5-prop-2-enyl-3,4-dihydroquinolin-2-one Chemical compound CC1=CC=C2N(C)C(=O)CCC2=C1CC=C BBJGFWURZYLXTC-UHFFFAOYSA-N 0.000 description 1
• UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
• IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
• VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
• HTRHNJKNDSYOKP-UHFFFAOYSA-N 1h-quinolin-2-one;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2NC(=O)C=CC2=C1 HTRHNJKNDSYOKP-UHFFFAOYSA-N 0.000 description 1
• PIPWSBOFSUJCCO-UHFFFAOYSA-N 2,2-dimethylpiperazine Chemical compound CC1(C)CNCCN1 PIPWSBOFSUJCCO-UHFFFAOYSA-N 0.000 description 1
• GJPVEZPWJHAMDI-UHFFFAOYSA-N 2-(3,6-dimethyl-2-oxo-1a,7b-dihydro-1h-cyclopropa[c]quinolin-7-yl)acetaldehyde Chemical compound C12=C(CC=O)C(C)=CC=C2N(C)C(=O)C2C1C2 GJPVEZPWJHAMDI-UHFFFAOYSA-N 0.000 description 1
• LSAIZUSCYGYEHF-UHFFFAOYSA-N 2-(6-methyl-2-oxo-3,4-dihydro-1h-quinolin-5-yl)acetaldehyde Chemical compound N1C(=O)CCC2=C(CC=O)C(C)=CC=C21 LSAIZUSCYGYEHF-UHFFFAOYSA-N 0.000 description 1
• SPCKHVPPRJWQRZ-UHFFFAOYSA-N 2-benzhydryloxy-n,n-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 SPCKHVPPRJWQRZ-UHFFFAOYSA-N 0.000 description 1
• DIPSNMBMRJTXDW-UHFFFAOYSA-N 3,6-dimethyl-7-prop-2-enyl-1a,7b-dihydro-1h-cyclopropa[c]quinolin-2-one Chemical compound C12=C(CC=C)C(C)=CC=C2N(C)C(=O)C2C1C2 DIPSNMBMRJTXDW-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
• LNKBDFVSILQKSI-UHFFFAOYSA-N 4-Chloro-3-methoxyaniline Chemical compound COC1=CC(N)=CC=C1Cl LNKBDFVSILQKSI-UHFFFAOYSA-N 0.000 description 1
• PSWDUSVQENSHKZ-UHFFFAOYSA-N 5-(3,3-dimethylpiperazin-1-yl)-2-methylquinoline Chemical compound C=1C=CC2=NC(C)=CC=C2C=1N1CCNC(C)(C)C1 PSWDUSVQENSHKZ-UHFFFAOYSA-N 0.000 description 1
• ZTCXTOCPMMQYQO-UHFFFAOYSA-N 5-(3,8-diazabicyclo[3.2.1]octan-3-yl)-2-methylquinoline Chemical compound C1C(N2)CCC2CN1C1=CC=CC2=NC(C)=CC=C21 ZTCXTOCPMMQYQO-UHFFFAOYSA-N 0.000 description 1
• WAAWQXBTQIEGEL-UHFFFAOYSA-N 5-bromo-6-methyl-1-oxidoquinolin-1-ium Chemical compound [O-][N+]1=CC=CC2=C(Br)C(C)=CC=C21 WAAWQXBTQIEGEL-UHFFFAOYSA-N 0.000 description 1
• CHONOBMGSBMLDE-UHFFFAOYSA-N 5-bromo-6-methylquinoline Chemical compound N1=CC=CC2=C(Br)C(C)=CC=C21 CHONOBMGSBMLDE-UHFFFAOYSA-N 0.000 description 1
• 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
• 108091032151 5-hydroxytryptamine receptor family Proteins 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
• DWUWPEUTFLWDHK-UHFFFAOYSA-N 6-chloro-5-hydroxy-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C1C=CC(Cl)=C2O DWUWPEUTFLWDHK-UHFFFAOYSA-N 0.000 description 1
• LYRFHQXQXXNQST-UHFFFAOYSA-N 6-methyl-5-prop-2-enyl-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C(CC=C)C(C)=CC=C21 LYRFHQXQXXNQST-UHFFFAOYSA-N 0.000 description 1
• FXRAZEGGBZUFBB-UHFFFAOYSA-N 7-bromo-3,6-dimethyl-1a,7b-dihydro-1h-cyclopropa[c]quinolin-2-one Chemical compound C12=C(Br)C(C)=CC=C2N(C)C(=O)C2C1C2 FXRAZEGGBZUFBB-UHFFFAOYSA-N 0.000 description 1
• 206010065040 AIDS dementia complex Diseases 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• 208000000103 Anorexia Nervosa Diseases 0.000 description 1
• 201000006062 Asperger syndrome Diseases 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 208000027448 Attention Deficit and Disruptive Behavior disease Diseases 0.000 description 1
• 206010003805 Autism Diseases 0.000 description 1
• 208000032841 Bulimia Diseases 0.000 description 1
• OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
• 206010008027 Cerebellar atrophy Diseases 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 description 1
• 241000699802 Cricetulus griseus Species 0.000 description 1
• 229920002785 Croscarmellose sodium Polymers 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
• 206010012225 Delirium tremens Diseases 0.000 description 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
• 201000010374 Down Syndrome 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
• 208000027534 Emotional disease Diseases 0.000 description 1
• 208000010228 Erectile Dysfunction Diseases 0.000 description 1
• 208000026097 Factitious disease Diseases 0.000 description 1
• 206010057671 Female sexual dysfunction Diseases 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 description 1
• 208000010235 Food Addiction Diseases 0.000 description 1
• 201000011240 Frontotemporal dementia Diseases 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• 208000011688 Generalised anxiety disease Diseases 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 229920002907 Guar gum Polymers 0.000 description 1
• 206010019196 Head injury Diseases 0.000 description 1
• 208000023105 Huntington disease Diseases 0.000 description 1
• 206010020880 Hypertrophy Diseases 0.000 description 1
• 208000016588 Idiopathic hypersomnia Diseases 0.000 description 1
• 206010061216 Infarction Diseases 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
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 206010026864 Masochism Diseases 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 description 1
• 239000004909 Moisturizer Substances 0.000 description 1
• 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
• BATFHSIVMJJJAF-UHFFFAOYSA-N Morindone Chemical compound OC1=CC=C2C(=O)C3=C(O)C(C)=CC=C3C(=O)C2=C1O BATFHSIVMJJJAF-UHFFFAOYSA-N 0.000 description 1
• 208000016285 Movement disease Diseases 0.000 description 1
• SBPRIAGPYFYCRT-UHFFFAOYSA-N N-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-N-(2-pyridinyl)cyclohexanecarboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCCCC2)C=2N=CC=CC=2)CC1 SBPRIAGPYFYCRT-UHFFFAOYSA-N 0.000 description 1
• 238000007126 N-alkylation reaction Methods 0.000 description 1
• 150000001204 N-oxides Chemical class 0.000 description 1
• 206010057852 Nicotine dependence Diseases 0.000 description 1
• 206010029412 Nightmare Diseases 0.000 description 1
• PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 1
• 208000008589 Obesity Diseases 0.000 description 1
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
• 235000019502 Orange oil Nutrition 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 206010033664 Panic attack Diseases 0.000 description 1
• 208000027099 Paranoid disease Diseases 0.000 description 1
• DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• 208000027089 Parkinsonian disease Diseases 0.000 description 1
• 206010034010 Parkinsonism Diseases 0.000 description 1
• 208000032769 Pedophilia Diseases 0.000 description 1
• RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 description 1
• 208000012202 Pervasive developmental disease Diseases 0.000 description 1
• RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 1
• 206010034912 Phobia Diseases 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
• 208000000609 Pick Disease of the Brain Diseases 0.000 description 1
• 206010052276 Pseudodementia Diseases 0.000 description 1
• 208000006262 Psychological Sexual Dysfunctions Diseases 0.000 description 1
• 208000006289 Rett Syndrome Diseases 0.000 description 1
• 208000036353 Rett disease Diseases 0.000 description 1
• XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 description 1
• 206010039367 Sadism Diseases 0.000 description 1
• 208000029899 Sexual aversion disease Diseases 0.000 description 1
• 208000030047 Sexual desire disease Diseases 0.000 description 1
• 208000019568 Shared Paranoid disease Diseases 0.000 description 1
• 206010041347 Somnambulism Diseases 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 208000006011 Stroke Diseases 0.000 description 1
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• 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 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
• KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 description 1
• GFBKORZTTCHDGY-UWVJOHFNSA-N Thiothixene Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2\C1=C\CCN1CCN(C)CC1 GFBKORZTTCHDGY-UWVJOHFNSA-N 0.000 description 1
• 208000025569 Tobacco Use disease Diseases 0.000 description 1
• KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 208000005386 Transient Global Amnesia Diseases 0.000 description 1
• 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
• 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
• HWHLPVGTWGOCJO-UHFFFAOYSA-N Trihexyphenidyl Chemical group C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 HWHLPVGTWGOCJO-UHFFFAOYSA-N 0.000 description 1
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
• SECKRCOLJRRGGV-UHFFFAOYSA-N Vardenafil Chemical compound CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 SECKRCOLJRRGGV-UHFFFAOYSA-N 0.000 description 1
• 108010046516 Wheat Germ Agglutinins Proteins 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
• 230000005856 abnormality Effects 0.000 description 1
• VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 238000001467 acupuncture Methods 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 208000026345 acute stress disease Diseases 0.000 description 1
• 239000000674 adrenergic antagonist Substances 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 230000007000 age related cognitive decline Effects 0.000 description 1
• 230000032683 aging Effects 0.000 description 1
• 206010001584 alcohol abuse Diseases 0.000 description 1
• 201000007930 alcohol dependence Diseases 0.000 description 1
• 208000025746 alcohol use disease Diseases 0.000 description 1
• 208000029650 alcohol withdrawal Diseases 0.000 description 1
• 208000006246 alcohol withdrawal delirium Diseases 0.000 description 1
• 230000001476 alcoholic effect Effects 0.000 description 1
• 125000003545 alkoxy group Chemical group 0.000 description 1
• 102000004305 alpha Adrenergic Receptors Human genes 0.000 description 1
• 108090000861 alpha Adrenergic Receptors Proteins 0.000 description 1
• 229960004538 alprazolam Drugs 0.000 description 1
• VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
• 229960000711 alprostadil Drugs 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
• 229960003805 amantadine Drugs 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 229960003036 amisulpride Drugs 0.000 description 1
• NTJOBXMMWNYJFB-UHFFFAOYSA-N amisulpride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC NTJOBXMMWNYJFB-UHFFFAOYSA-N 0.000 description 1
• 229960000836 amitriptyline Drugs 0.000 description 1
• KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
• 235000011114 ammonium hydroxide Nutrition 0.000 description 1
• 201000002472 amphetamine abuse Diseases 0.000 description 1
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
• 239000003263 anabolic agent Substances 0.000 description 1
• 229940070021 anabolic steroids Drugs 0.000 description 1
• 230000008485 antagonism Effects 0.000 description 1
• 229940125713 antianxiety drug Drugs 0.000 description 1
• 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
• 229940125715 antihistaminic agent Drugs 0.000 description 1
• 239000000739 antihistaminic agent Substances 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 230000003078 antioxidant effect Effects 0.000 description 1
• 235000006708 antioxidants Nutrition 0.000 description 1
• 239000003420 antiserotonin agent Substances 0.000 description 1
• 208000024823 antisocial personality disease Diseases 0.000 description 1
• 229960004046 apomorphine Drugs 0.000 description 1
• VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 229940072107 ascorbate Drugs 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• 239000003693 atypical antipsychotic agent Substances 0.000 description 1
• 229940127236 atypical antipsychotics Drugs 0.000 description 1
• GIJXKZJWITVLHI-PMOLBWCYSA-N benzatropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(C=1C=CC=CC=1)C1=CC=CC=C1 GIJXKZJWITVLHI-PMOLBWCYSA-N 0.000 description 1
• 229960001081 benzatropine Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• 229940049706 benzodiazepine Drugs 0.000 description 1
• 150000001557 benzodiazepines Chemical class 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 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
• 230000015572 biosynthetic process Effects 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 239000012267 brine Substances 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• 229960001058 bupropion Drugs 0.000 description 1
• SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• 235000013539 calcium stearate Nutrition 0.000 description 1
• GJYLKIZKRHDRER-UHFFFAOYSA-N calcium;sulfuric acid Chemical compound [Ca].OS(O)(=O)=O GJYLKIZKRHDRER-UHFFFAOYSA-N 0.000 description 1
• 201000009322 cannabis abuse Diseases 0.000 description 1
• 239000007894 caplet Substances 0.000 description 1
• 229960000623 carbamazepine Drugs 0.000 description 1
• FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
• 150000001721 carbon Chemical group 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 238000006555 catalytic reaction Methods 0.000 description 1
• 210000000170 cell membrane Anatomy 0.000 description 1
• 238000005119 centrifugation Methods 0.000 description 1
• 150000001793 charged compounds Chemical class 0.000 description 1
• 239000002738 chelating agent Substances 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 239000003638 chemical reducing agent Substances 0.000 description 1
• 208000024825 childhood disintegrative disease Diseases 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 229960001076 chlorpromazine Drugs 0.000 description 1
• ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
• 239000000812 cholinergic antagonist Substances 0.000 description 1
• 239000000544 cholinesterase inhibitor Substances 0.000 description 1
• 238000011097 chromatography purification Methods 0.000 description 1
• 230000027288 circadian rhythm Effects 0.000 description 1
• 229940001468 citrate Drugs 0.000 description 1
• 229960004606 clomipramine 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
• 239000011248 coating agent Substances 0.000 description 1
• 201000001272 cocaine abuse Diseases 0.000 description 1
• 230000006999 cognitive decline Effects 0.000 description 1
• 230000037410 cognitive enhancement Effects 0.000 description 1
• 230000003920 cognitive function Effects 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 239000006184 cosolvent Substances 0.000 description 1
• 235000019788 craving Nutrition 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 229960005168 croscarmellose Drugs 0.000 description 1
• 229960000913 crospovidone Drugs 0.000 description 1
• 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 208000030964 dependent personality disease Diseases 0.000 description 1
• 238000010511 deprotection reaction Methods 0.000 description 1
• 230000001066 destructive effect Effects 0.000 description 1
• 229910052805 deuterium Inorganic materials 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• 239000008121 dextrose Substances 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
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
• 229940038472 dicalcium phosphate Drugs 0.000 description 1
• 229960000520 diphenhydramine Drugs 0.000 description 1
• 208000035548 disruptive behavior disease Diseases 0.000 description 1
• 238000009826 distribution Methods 0.000 description 1
• 229960003530 donepezil Drugs 0.000 description 1
• 229960003638 dopamine Drugs 0.000 description 1
• 229940052760 dopamine agonists Drugs 0.000 description 1
• 229960002866 duloxetine Drugs 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 239000003480 eluent Substances 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 230000002708 enhancing effect Effects 0.000 description 1
• 206010015037 epilepsy Diseases 0.000 description 1
• 210000000981 epithelium Anatomy 0.000 description 1
• 229960005309 estradiol Drugs 0.000 description 1
• 229930182833 estradiol Natural products 0.000 description 1
• 229940011871 estrogen Drugs 0.000 description 1
• 239000000262 estrogen Substances 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 235000019634 flavors Nutrition 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 229960002690 fluphenazine Drugs 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 238000009472 formulation Methods 0.000 description 1
• 229960002870 gabapentin Drugs 0.000 description 1
• 229960003980 galantamine Drugs 0.000 description 1
• ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 208000029364 generalized anxiety disease Diseases 0.000 description 1
• 229940050410 gluconate Drugs 0.000 description 1
• MFWNKCLOYSRHCJ-BTTYYORXSA-N granisetron Chemical compound C1=CC=C2C(C(=O)N[C@H]3C[C@H]4CCC[C@@H](C3)N4C)=NN(C)C2=C1 MFWNKCLOYSRHCJ-BTTYYORXSA-N 0.000 description 1
• 229960003727 granisetron Drugs 0.000 description 1
• 239000003979 granulating agent Substances 0.000 description 1
• 239000000665 guar gum Substances 0.000 description 1
• 235000010417 guar gum Nutrition 0.000 description 1
• 229960002154 guar gum Drugs 0.000 description 1
• 201000002270 hallucinogen abuse Diseases 0.000 description 1
• 229960003878 haloperidol Drugs 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 229940071870 hydroiodic acid Drugs 0.000 description 1
• 208000003532 hypothyroidism Diseases 0.000 description 1
• 230000002989 hypothyroidism Effects 0.000 description 1
• 229960004801 imipramine Drugs 0.000 description 1
• BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
• 230000001771 impaired effect Effects 0.000 description 1
• 201000001881 impotence Diseases 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• SADQVAVFGNTEOD-UHFFFAOYSA-N indalpine Chemical compound C=1NC2=CC=CC=C2C=1CCC1CCNCC1 SADQVAVFGNTEOD-UHFFFAOYSA-N 0.000 description 1
• 229950002473 indalpine Drugs 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 230000007574 infarction Effects 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 230000035987 intoxication Effects 0.000 description 1
• 231100000566 intoxication Toxicity 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• 238000005342 ion exchange Methods 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• 229960002672 isocarboxazid Drugs 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 description 1
• 229960001848 lamotrigine Drugs 0.000 description 1
• 230000008449 language Effects 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 229960004391 lorazepam Drugs 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 229960000423 loxapine Drugs 0.000 description 1
• XJGVXQDUIWGIRW-UHFFFAOYSA-N loxapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 XJGVXQDUIWGIRW-UHFFFAOYSA-N 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 208000015421 male orgasm disease Diseases 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 229960004090 maprotiline Drugs 0.000 description 1
• 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 1
• 230000000873 masking effect Effects 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• 229960000300 mesoridazine Drugs 0.000 description 1
• SLVMESMUVMCQIY-UHFFFAOYSA-N mesoridazine Chemical compound CN1CCCCC1CCN1C2=CC(S(C)=O)=CC=C2SC2=CC=CC=C21 SLVMESMUVMCQIY-UHFFFAOYSA-N 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 229960003955 mianserin Drugs 0.000 description 1
• 208000027061 mild cognitive impairment Diseases 0.000 description 1
• 229960000600 milnacipran Drugs 0.000 description 1
• 150000007522 mineralic acids Chemical class 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
• 241000514897 mixed subtypes Species 0.000 description 1
• 230000001333 moisturizer Effects 0.000 description 1
• 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
• 201000003631 narcolepsy Diseases 0.000 description 1
• 230000004770 neurodegeneration Effects 0.000 description 1
• 239000003176 neuroleptic agent Substances 0.000 description 1
• 230000000701 neuroleptic effect Effects 0.000 description 1
• 231100000189 neurotoxic Toxicity 0.000 description 1
• 230000002887 neurotoxic effect Effects 0.000 description 1
• 239000001272 nitrous oxide Substances 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 239000002664 nootropic agent Substances 0.000 description 1
• 230000001777 nootropic effect Effects 0.000 description 1
• 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 1
• 229960001158 nortriptyline Drugs 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 235000020824 obesity Nutrition 0.000 description 1
• 208000030459 obsessive-compulsive personality disease Diseases 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 239000003921 oil Substances 0.000 description 1
• 235000019198 oils Nutrition 0.000 description 1
• 239000002674 ointment Substances 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
• 229960005343 ondansetron Drugs 0.000 description 1
• 201000005040 opiate dependence Diseases 0.000 description 1
• 201000000988 opioid abuse Diseases 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 239000010502 orange oil Substances 0.000 description 1
• 229910000487 osmium oxide Inorganic materials 0.000 description 1
• 210000001672 ovary Anatomy 0.000 description 1
• JIWAALDUIFCBLV-UHFFFAOYSA-N oxoosmium Chemical compound [Os]=O JIWAALDUIFCBLV-UHFFFAOYSA-N 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 229960001779 pargyline Drugs 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 229960000762 perphenazine Drugs 0.000 description 1
• 229940124531 pharmaceutical excipient Drugs 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 229960000964 phenelzine Drugs 0.000 description 1
• 229960001999 phentolamine Drugs 0.000 description 1
• MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
• RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 239000002590 phosphodiesterase V inhibitor Substances 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• 208000024335 physical disease Diseases 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 239000004014 plasticizer Substances 0.000 description 1
• 229920001992 poloxamer 407 Polymers 0.000 description 1
• 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
• 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 208000028173 post-traumatic stress disease Diseases 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 229940069328 povidone Drugs 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 239000002243 precursor Substances 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 229960003111 prochlorperazine Drugs 0.000 description 1
• WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 1
• 229960005253 procyclidine Drugs 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
• 150000003180 prostaglandins Chemical class 0.000 description 1
• 229960004431 quetiapine Drugs 0.000 description 1
• URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
• 229930185107 quinolinone Natural products 0.000 description 1
• 230000002285 radioactive effect Effects 0.000 description 1
• 239000002287 radioligand Substances 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 239000013557 residual solvent Substances 0.000 description 1
• 230000000241 respiratory effect Effects 0.000 description 1
• 238000012552 review Methods 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
• 229960004136 rivastigmine Drugs 0.000 description 1
• 239000012047 saturated solution Substances 0.000 description 1
• 238000003345 scintillation counting Methods 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 238000013207 serial dilution Methods 0.000 description 1
• 229940076279 serotonin Drugs 0.000 description 1
• 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 1
• 239000000952 serotonin receptor agonist Substances 0.000 description 1
• 208000012201 sexual and gender identity disease Diseases 0.000 description 1
• 230000035946 sexual desire Effects 0.000 description 1
• 208000015891 sexual disease Diseases 0.000 description 1
• 201000005814 sexual masochism Diseases 0.000 description 1
• 208000027599 sexual masochism disease Diseases 0.000 description 1
• 201000005841 sexual sadism Diseases 0.000 description 1
• 208000027596 sexual sadism disease Diseases 0.000 description 1
• 230000035939 shock Effects 0.000 description 1
• 229960003310 sildenafil Drugs 0.000 description 1
• 235000010413 sodium alginate Nutrition 0.000 description 1
• 239000000661 sodium alginate Substances 0.000 description 1
• 229940005550 sodium alginate Drugs 0.000 description 1
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
• 239000008109 sodium starch glycolate Substances 0.000 description 1
• 229920003109 sodium starch glycolate Polymers 0.000 description 1
• 229940079832 sodium starch glycolate Drugs 0.000 description 1
• AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 1
• 229940084026 sodium valproate Drugs 0.000 description 1
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 235000010356 sorbitol Nutrition 0.000 description 1
• 201000001716 specific phobia Diseases 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 239000008174 sterile solution Substances 0.000 description 1
• 231100000736 substance abuse Toxicity 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 229910052717 sulfur Inorganic materials 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1
• KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 1
• 229960003708 sumatriptan Drugs 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 229960001685 tacrine Drugs 0.000 description 1
• YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• HNINFCBLGHCFOJ-UHFFFAOYSA-N tert-butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate Chemical compound C1NCC2CCC1N2C(=O)OC(C)(C)C HNINFCBLGHCFOJ-UHFFFAOYSA-N 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• 229960002784 thioridazine Drugs 0.000 description 1
• 229960001918 tiagabine Drugs 0.000 description 1
• PBJUNZJWGZTSKL-MRXNPFEDSA-N tiagabine Chemical compound C1=CSC(C(=CCCN2C[C@@H](CCC2)C(O)=O)C2=C(C=CS2)C)=C1C PBJUNZJWGZTSKL-MRXNPFEDSA-N 0.000 description 1
• 208000016686 tic disease Diseases 0.000 description 1
• 229960005013 tiotixene Drugs 0.000 description 1
• 210000001519 tissue Anatomy 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
• 238000011200 topical administration Methods 0.000 description 1
• 229960004394 topiramate Drugs 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 229960003741 tranylcypromine Drugs 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
• 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
• ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
• 229960002324 trifluoperazine Drugs 0.000 description 1
• 229960001032 trihexyphenidyl Drugs 0.000 description 1
• 229960002431 trimipramine Drugs 0.000 description 1
• ZSCDBOWYZJWBIY-UHFFFAOYSA-N trimipramine Chemical compound C1CC2=CC=CC=C2N(CC(CN(C)C)C)C2=CC=CC=C21 ZSCDBOWYZJWBIY-UHFFFAOYSA-N 0.000 description 1
• IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
• 229910052722 tritium Inorganic materials 0.000 description 1
• 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
• 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
• 238000002211 ultraviolet spectrum Methods 0.000 description 1
• 206010046947 vaginismus Diseases 0.000 description 1
• 229960002381 vardenafil Drugs 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 229960004688 venlafaxine Drugs 0.000 description 1
• PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
• 239000003643 water by type Substances 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 229940075420 xanthine Drugs 0.000 description 1
• 229960000317 yohimbine Drugs 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
• 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