IL299451A - מיצוי אלקלואיד פסיכואקטיבי מפוספס בעיקר באמצעות אלקלי - Google Patents
מיצוי אלקלואיד פסיכואקטיבי מפוספס בעיקר באמצעות אלקליInfo
- Publication number
- IL299451A IL299451A IL299451A IL29945122A IL299451A IL 299451 A IL299451 A IL 299451A IL 299451 A IL299451 A IL 299451A IL 29945122 A IL29945122 A IL 29945122A IL 299451 A IL299451 A IL 299451A
- Authority
- IL
- Israel
- Prior art keywords
- psychoactive
- alkaloid
- solvent
- weight
- psychoactive alkaloid
- Prior art date
Links
- 229930013930 alkaloid Natural products 0.000 title claims description 1073
- 150000003797 alkaloid derivatives Chemical class 0.000 title claims description 962
- 238000000605 extraction Methods 0.000 title description 171
- 239000003513 alkali Substances 0.000 title description 4
- 239000002904 solvent Substances 0.000 claims description 377
- 239000000203 mixture Substances 0.000 claims description 367
- 239000000284 extract Substances 0.000 claims description 330
- 238000000034 method Methods 0.000 claims description 172
- 239000002002 slurry Substances 0.000 claims description 137
- 239000002028 Biomass Substances 0.000 claims description 126
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 114
- QVDSEJDULKLHCG-UHFFFAOYSA-N Psilocybine Natural products C1=CC(OP(O)(O)=O)=C2C(CCN(C)C)=CNC2=C1 QVDSEJDULKLHCG-UHFFFAOYSA-N 0.000 claims description 104
- 229910001868 water Inorganic materials 0.000 claims description 96
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 66
- 239000007788 liquid Substances 0.000 claims description 65
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 51
- 238000001704 evaporation Methods 0.000 claims description 49
- WTPBXXCVZZZXKR-UHFFFAOYSA-N baeocystin Chemical compound C1=CC(OP(O)(O)=O)=C2C(CCNC)=CNC2=C1 WTPBXXCVZZZXKR-UHFFFAOYSA-N 0.000 claims description 46
- 239000007787 solid Substances 0.000 claims description 45
- SPCIYGNTAMCTRO-UHFFFAOYSA-N Psilocine Natural products C1=CC(O)=C2C(CCN(C)C)=CNC2=C1 SPCIYGNTAMCTRO-UHFFFAOYSA-N 0.000 claims description 44
- ZBWSBXGHYDWMAK-UHFFFAOYSA-N psilocin Chemical compound C1=CC=C(O)[C]2C(CCN(C)C)=CN=C21 ZBWSBXGHYDWMAK-UHFFFAOYSA-N 0.000 claims description 44
- IKQGYCWFBVEAKF-UHFFFAOYSA-N norbaeocystin Chemical compound C1=CC(OP(O)(O)=O)=C2C(CCN)=CNC2=C1 IKQGYCWFBVEAKF-UHFFFAOYSA-N 0.000 claims description 42
- WVVSZNPYNCNODU-CJBNDPTMSA-N Ergometrine Natural products C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-CJBNDPTMSA-N 0.000 claims description 33
- WVVSZNPYNCNODU-XTQGRXLLSA-N Lysergic acid propanolamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-XTQGRXLLSA-N 0.000 claims description 33
- ZSTKHSQDNIGFLM-UHFFFAOYSA-N 5-methoxy-N,N-dimethyltryptamine Chemical compound COC1=CC=C2NC=C(CCN(C)C)C2=C1 ZSTKHSQDNIGFLM-UHFFFAOYSA-N 0.000 claims description 32
- 238000001035 drying Methods 0.000 claims description 31
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 30
- 150000002576 ketones Chemical class 0.000 claims description 29
- 235000019832 sodium triphosphate Nutrition 0.000 claims description 27
- DMULVCHRPCFFGV-UHFFFAOYSA-N N,N-dimethyltryptamine Chemical compound C1=CC=C2C(CCN(C)C)=CNC2=C1 DMULVCHRPCFFGV-UHFFFAOYSA-N 0.000 claims description 25
- 241001062357 Psilocybe cubensis Species 0.000 claims description 25
- VTTONGPRPXSUTJ-UHFFFAOYSA-N bufotenin Chemical compound C1=C(O)C=C2C(CCN(C)C)=CNC2=C1 VTTONGPRPXSUTJ-UHFFFAOYSA-N 0.000 claims description 22
- 229960001405 ergometrine Drugs 0.000 claims description 22
- WYTJZJPVCDWOOI-KANYHAFZSA-N lysergic acid hydroxyethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@@H](O)C)C2)=C3C2=CNC3=C1 WYTJZJPVCDWOOI-KANYHAFZSA-N 0.000 claims description 22
- ZJQHPWUVQPJPQT-UHFFFAOYSA-N muscimol Chemical compound NCC1=CC(=O)NO1 ZJQHPWUVQPJPQT-UHFFFAOYSA-N 0.000 claims description 22
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 20
- 230000008020 evaporation Effects 0.000 claims description 20
- MTJOWJUQGYWRHT-UHFFFAOYSA-N 3-[2-(methylamino)ethyl]-1h-indol-4-ol Chemical compound C1=CC(O)=C2C(CCNC)=CNC2=C1 MTJOWJUQGYWRHT-UHFFFAOYSA-N 0.000 claims description 19
- OIIPFLWAQQNCHA-UHFFFAOYSA-N aeruginascin Chemical compound C1=CC(OP(O)([O-])=O)=C2C(CC[N+](C)(C)C)=CNC2=C1 OIIPFLWAQQNCHA-UHFFFAOYSA-N 0.000 claims description 19
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 claims description 18
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 18
- 239000001099 ammonium carbonate Substances 0.000 claims description 18
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 claims description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
- 239000001540 sodium lactate Substances 0.000 claims description 18
- 235000011088 sodium lactate Nutrition 0.000 claims description 18
- 229940005581 sodium lactate Drugs 0.000 claims description 18
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 claims description 18
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 18
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 17
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 14
- IRJCBFDCFXCWGO-BYPYZUCNSA-N (2s)-2-amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid Chemical compound OC(=O)[C@@H](N)C1=CC(=O)NO1 IRJCBFDCFXCWGO-BYPYZUCNSA-N 0.000 claims description 13
- IRJCBFDCFXCWGO-UHFFFAOYSA-N Ibotenic acid Natural products OC(=O)C(N)C1=CC(=O)NO1 IRJCBFDCFXCWGO-UHFFFAOYSA-N 0.000 claims description 13
- 229940078495 calcium phosphate dibasic Drugs 0.000 claims description 13
- YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 claims description 12
- FKIRTWDHOWAQGX-UHFFFAOYSA-N 4-hydroxytryptamine Chemical compound C1=CC(O)=C2C(CCN)=CNC2=C1 FKIRTWDHOWAQGX-UHFFFAOYSA-N 0.000 claims description 11
- GENAHGKEFJLNJB-QMTHXVAHSA-N Ergine Natural products C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(N)=O)=C3C2=CNC3=C1 GENAHGKEFJLNJB-QMTHXVAHSA-N 0.000 claims description 11
- SAHHMCVYMGARBT-UHFFFAOYSA-N Isochanoclavine I Natural products C1=CC(C(C(NC)C2)C=C(C)CO)=C3C2=CNC3=C1 SAHHMCVYMGARBT-UHFFFAOYSA-N 0.000 claims description 11
- GENAHGKEFJLNJB-UHFFFAOYSA-N Lysergsaeure-amid Natural products C1=CC(C2=CC(CN(C2C2)C)C(N)=O)=C3C2=CNC3=C1 GENAHGKEFJLNJB-UHFFFAOYSA-N 0.000 claims description 11
- HIYGARYIJIZXGW-UHFFFAOYSA-N bufotenidine Chemical compound C1=C([O-])C=C2C(CC[N+](C)(C)C)=CNC2=C1 HIYGARYIJIZXGW-UHFFFAOYSA-N 0.000 claims description 11
- SAHHMCVYMGARBT-HEESEWQSSA-N chanoclavine-I Chemical compound C1=CC([C@H]([C@H](NC)C2)\C=C(/C)CO)=C3C2=CNC3=C1 SAHHMCVYMGARBT-HEESEWQSSA-N 0.000 claims description 11
- DAVNRFCJMIONPO-UHFFFAOYSA-N elymoclavine Natural products C1=CC(C2C=C(CO)CN(C2C2)C)=C3C2=CNC3=C1 DAVNRFCJMIONPO-UHFFFAOYSA-N 0.000 claims description 11
- IAOSEBXZNXDPEE-UKRRQHHQSA-N elymoclavine Chemical compound C1=CC=C2[C@H]3C=C(CO)CN(C)[C@@H]3CC3=CN=C1[C]32 IAOSEBXZNXDPEE-UKRRQHHQSA-N 0.000 claims description 11
- YDPHSKXTPWQXBA-QMTHXVAHSA-N ergine Chemical compound C1=CC=C2C3=C[C@@H](C(N)=O)CN(C)[C@@H]3CC3=CN=C1[C]32 YDPHSKXTPWQXBA-QMTHXVAHSA-N 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 241000134914 Amanita muscaria Species 0.000 claims description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 10
- 241000332761 Psilocybe cyanescens Species 0.000 claims description 10
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 10
- 239000000908 ammonium hydroxide Substances 0.000 claims description 10
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 10
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 10
- 235000010216 calcium carbonate Nutrition 0.000 claims description 10
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 10
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims description 9
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 9
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 9
- ZQKXOSJYJMDROL-UHFFFAOYSA-H aluminum;trisodium;diphosphate Chemical compound [Na+].[Na+].[Na+].[Al+3].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O ZQKXOSJYJMDROL-UHFFFAOYSA-H 0.000 claims description 9
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims description 9
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 9
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims description 9
- 235000011092 calcium acetate Nutrition 0.000 claims description 9
- 239000001639 calcium acetate Substances 0.000 claims description 9
- 229960005147 calcium acetate Drugs 0.000 claims description 9
- 239000001110 calcium chloride Substances 0.000 claims description 9
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 9
- 235000011148 calcium chloride Nutrition 0.000 claims description 9
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 9
- 239000000920 calcium hydroxide Substances 0.000 claims description 9
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 9
- 235000011116 calcium hydroxide Nutrition 0.000 claims description 9
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 claims description 9
- 239000001527 calcium lactate Substances 0.000 claims description 9
- 235000011086 calcium lactate Nutrition 0.000 claims description 9
- 229960002401 calcium lactate Drugs 0.000 claims description 9
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000292 calcium oxide Substances 0.000 claims description 9
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 9
- 235000012255 calcium oxide Nutrition 0.000 claims description 9
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 9
- 235000019820 disodium diphosphate Nutrition 0.000 claims description 9
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 9
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 9
- 235000019800 disodium phosphate Nutrition 0.000 claims description 9
- GYQBBRRVRKFJRG-UHFFFAOYSA-L disodium pyrophosphate Chemical compound [Na+].[Na+].OP([O-])(=O)OP(O)([O-])=O GYQBBRRVRKFJRG-UHFFFAOYSA-L 0.000 claims description 9
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 9
- 239000001095 magnesium carbonate Substances 0.000 claims description 9
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 9
- 239000011591 potassium Substances 0.000 claims description 9
- 229910052700 potassium Inorganic materials 0.000 claims description 9
- GRLPQNLYRHEGIJ-UHFFFAOYSA-J potassium aluminium sulfate Chemical compound [Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRLPQNLYRHEGIJ-UHFFFAOYSA-J 0.000 claims description 9
- 239000011736 potassium bicarbonate Substances 0.000 claims description 9
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 9
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
- 235000011181 potassium carbonates Nutrition 0.000 claims description 9
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 9
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 claims description 9
- 235000011085 potassium lactate Nutrition 0.000 claims description 9
- 239000001521 potassium lactate Substances 0.000 claims description 9
- 229960001304 potassium lactate Drugs 0.000 claims description 9
- 239000001632 sodium acetate Substances 0.000 claims description 9
- 235000017281 sodium acetate Nutrition 0.000 claims description 9
- GJPYYNMJTJNYTO-UHFFFAOYSA-J sodium aluminium sulfate Chemical compound [Na+].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GJPYYNMJTJNYTO-UHFFFAOYSA-J 0.000 claims description 9
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 claims description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 9
- 235000017550 sodium carbonate Nutrition 0.000 claims description 9
- 235000019982 sodium hexametaphosphate Nutrition 0.000 claims description 9
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 claims description 9
- 229940083608 sodium hydroxide Drugs 0.000 claims description 9
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 claims description 9
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 claims description 9
- 229910000404 tripotassium phosphate Inorganic materials 0.000 claims description 9
- 235000019798 tripotassium phosphate Nutrition 0.000 claims description 9
- 229910000406 trisodium phosphate Inorganic materials 0.000 claims description 9
- 238000010298 pulverizing process Methods 0.000 claims description 8
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 8
- 235000019801 trisodium phosphate Nutrition 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019797 dipotassium phosphate Nutrition 0.000 claims description 4
- 229910000396 dipotassium phosphate Inorganic materials 0.000 claims description 4
- 239000012260 resinous material Substances 0.000 claims description 2
- QKTAAWLCLHMUTJ-UHFFFAOYSA-N psilocybin Chemical compound C1C=CC(OP(O)(O)=O)=C2C(CCN(C)C)=CN=C21 QKTAAWLCLHMUTJ-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 202
- 230000008569 process Effects 0.000 description 115
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- 239000002253 acid Substances 0.000 description 72
- 239000000243 solution Substances 0.000 description 72
- 239000000706 filtrate Substances 0.000 description 68
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 60
- 239000003755 preservative agent Substances 0.000 description 60
- 239000011347 resin Substances 0.000 description 59
- 229920005989 resin Polymers 0.000 description 59
- 239000002585 base Substances 0.000 description 54
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 48
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 45
- 239000003795 chemical substances by application Substances 0.000 description 45
- 241000233866 Fungi Species 0.000 description 35
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- 239000000463 material Substances 0.000 description 30
- 238000001914 filtration Methods 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 28
- 230000002335 preservative effect Effects 0.000 description 27
- 238000000746 purification Methods 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 24
- 235000011007 phosphoric acid Nutrition 0.000 description 24
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 23
- 235000010323 ascorbic acid Nutrition 0.000 description 23
- 239000011668 ascorbic acid Substances 0.000 description 23
- 229960005070 ascorbic acid Drugs 0.000 description 23
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 23
- 230000001337 psychedelic effect Effects 0.000 description 23
- 239000003463 adsorbent Substances 0.000 description 22
- 239000012535 impurity Substances 0.000 description 22
- 239000002245 particle Substances 0.000 description 21
- 229920002774 Maltodextrin Polymers 0.000 description 20
- 239000005913 Maltodextrin Substances 0.000 description 20
- 229960004106 citric acid Drugs 0.000 description 20
- 229940035034 maltodextrin Drugs 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- 238000005406 washing Methods 0.000 description 19
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 18
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 18
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 18
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 18
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 17
- 239000004615 ingredient Substances 0.000 description 17
- 230000002829 reductive effect Effects 0.000 description 17
- 235000011167 hydrochloric acid Nutrition 0.000 description 16
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 16
- 238000002156 mixing Methods 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- 238000001223 reverse osmosis Methods 0.000 description 16
- 239000001509 sodium citrate Substances 0.000 description 16
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 16
- 235000011083 sodium citrates Nutrition 0.000 description 16
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Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
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| US202063040317P | 2020-06-17 | 2020-06-17 | |
| US202063046089P | 2020-06-30 | 2020-06-30 | |
| CA3088384A CA3088384C (en) | 2020-06-17 | 2020-07-29 | Extraction of psychoactive compounds from psilocybin fungus |
| CA3089455A CA3089455C (en) | 2020-06-17 | 2020-08-07 | Methanol-based extraction of psychoactive compounds from fungus |
| CA3097246A CA3097246C (en) | 2020-10-23 | 2020-10-23 | Process for obtaining a purified psychoactive alkaloid solution |
| CA3101765A CA3101765A1 (en) | 2020-12-04 | 2020-12-04 | Psychoactive alkaloid extraction and composition with controlled dephosphorylation |
| CA3103707A CA3103707C (en) | 2020-12-18 | 2020-12-18 | Standardized psychoactive alkaloid extract composition |
| PCT/CA2021/050813 WO2021253116A1 (en) | 2020-06-17 | 2021-06-14 | Compositions comprising psychoactive compounds from psychoactive organisms |
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| IL297791A IL297791A (he) | 2020-06-17 | 2021-06-14 | תרכובות המורכבות תרכובות פסיכואקטיביות מאורגניזמים פסיכואקטיביים |
| IL299451A IL299451A (he) | 2020-06-17 | 2021-06-14 | מיצוי אלקלואיד פסיכואקטיבי מפוספס בעיקר באמצעות אלקלי |
| IL299450A IL299450A (he) | 2020-06-17 | 2021-06-14 | מיצוי מבוקרת דה-פוספורילציה של אלקלואידים פסיכואקטיביים הניתנים לזרחני |
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| IL299453A IL299453A (he) | 2020-06-17 | 2021-06-14 | מיצוי והרכב אלקלואידים פסיכואקטיביים עם דה-פוספורילציה מעוכבת |
| IL298561A IL298561A (he) | 2020-06-17 | 2021-06-14 | מיצוי על בסיס מתנול של תרכובות פסיכואקטיביות מפטריה |
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| IL297791A IL297791A (he) | 2020-06-17 | 2021-06-14 | תרכובות המורכבות תרכובות פסיכואקטיביות מאורגניזמים פסיכואקטיביים |
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| IL299448A IL299448A (he) | 2020-06-17 | 2021-06-14 | תהליך להשגת תמיסת אלקלואיד פסיכואקטיבית מטוהרת |
| IL299453A IL299453A (he) | 2020-06-17 | 2021-06-14 | מיצוי והרכב אלקלואידים פסיכואקטיביים עם דה-פוספורילציה מעוכבת |
| IL298561A IL298561A (he) | 2020-06-17 | 2021-06-14 | מיצוי על בסיס מתנול של תרכובות פסיכואקטיביות מפטריה |
| IL299449A IL299449A (he) | 2020-06-17 | 2021-06-14 | הרכב תמצית אלקלואיד פסיכואקטיבי סטנדרטי |
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| EP (1) | EP4161546A1 (he) |
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| KR20220092509A (ko) | 2019-10-01 | 2022-07-01 | 엠피리언 뉴로사이언스, 인크. | 트립타민 발현을 조절하는 균류의 유전자 공학 |
| CA3197443A1 (en) | 2020-12-28 | 2022-06-28 | Psilo Scientific Ltd. | Processes for extracting psychoactive alkaloids and preparation thereof into transmucosal forms |
| WO2023225186A1 (en) * | 2022-05-18 | 2023-11-23 | Chemtor, Lp | Extraction of psilocybin and psilocin |
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| GB911946A (en) | 1958-02-21 | 1962-12-05 | Sandoz Ltd | Psilocybin and psilocin and processes for their preparation |
| LU36879A1 (he) | 1958-02-21 | |||
| DD264023A1 (de) * | 1987-07-17 | 1989-01-18 | Akad Wissenschaften Ddr | Verfahren zur extraktion von indolalkaloiden aus pilzmaterial |
| US6596298B2 (en) | 1998-09-25 | 2003-07-22 | Warner-Lambert Company | Fast dissolving orally comsumable films |
| US7671203B2 (en) | 2002-02-28 | 2010-03-02 | Mallinckrodt Inc. | Method and system for separation and purification of at least one narcotic alkaloid using reverse phase preparative chromatography |
| SE0302947D0 (sv) | 2003-01-24 | 2003-11-07 | Magle Ab | A composition material for transmucosal delivery |
| PL2063861T3 (pl) | 2006-09-15 | 2015-07-31 | Echo Pharmaceuticals Bv | Jednostka dawkowania do podawania podjęzykowego, podpoliczkowego lub doustnego nierozpuszczalnych w wodzie substancji aktywnych farmaceutycznie |
| CN101292727A (zh) | 2008-05-30 | 2008-10-29 | 曹晋忠 | 菌类乙醇提取物的粉体制备方法 |
| ES2829386T3 (es) | 2010-03-30 | 2021-05-31 | Phosphagenics Ltd | Parche de administración transdérmica |
| PL3160565T3 (pl) | 2014-06-30 | 2022-01-10 | Syqe Medical Ltd. | Urządzenia i systemy do dopłucnego dostarczania środków aktywnych |
| US20180021326A1 (en) | 2016-07-23 | 2018-01-25 | Paul Edward Stamets | Compositions and methods for enhancing neuroregeneration and cognition by combining mushroom extracts containing active ingredients psilocin or psilocybin with erinacines or hericenones enhanced with niacin |
| NL2018190B1 (en) | 2017-01-18 | 2018-07-26 | Procare Beheer B V | Psilocybin or psilocin in combination with cannabinoid |
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| US20190142851A1 (en) | 2017-11-16 | 2019-05-16 | CaaMTech, LLC | Compositions comprising a psilocybin derivative and a cannabinoid |
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| KR20210141968A (ko) | 2019-03-07 | 2021-11-23 | 아보멘티스 엘엘씨 | 비-환각/정신병유사 투여량 및 제형으로 투여되는 신경 가소성 작용을 갖는 물질을 포함하는 조성물 및 사용 방법 |
| US20220194992A1 (en) | 2019-04-26 | 2022-06-23 | The University Of North Carolina At Chapel Hill | Methods and compositions for dual glycan binding aav2.5 vector |
| CA3097246C (en) | 2020-10-23 | 2023-03-28 | Psilo Scientific Ltd. | Process for obtaining a purified psychoactive alkaloid solution |
| CA3088384C (en) | 2020-06-17 | 2021-08-03 | Psilo Scientific Ltd. | Extraction of psychoactive compounds from psilocybin fungus |
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| US20220054402A1 (en) | 2020-11-05 | 2022-02-24 | Richard C Kaufman | Compositions and methods for extracting, stabilizing, and manufacturing stable dosage forms of psilocin, psychedelic drugs, entheogens, and medicinal mushrooms as nano-dimensional drug delivery structures |
| US20220331292A1 (en) | 2021-04-16 | 2022-10-20 | Callitas Health Inc. | Compositions and methods for delivery of psilocin and prodrugs thereof |
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