3-(2-(dimethylamino)ethyl)-1H-indol-4-ol [Psilocin] by Asch

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Date

7 substances in Reaxys

2016-06-08 03h:05m:29s (EST)

N OH

1. Query

Search as: As drawn

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Reaxys ID 160503 View in Reaxys

1/7 CAS Registry Number: 520-53-6 Chemical Name: psilocin; Psilocine; PAL-153; 4-hydroxy-N,Ndimethyltryptamine; Psilocin; 3-(2-dimethylamino-ethyl)-indol-4ol; 3-(2-Dimethylamino-aethyl)-indol-4-ol Linear Structure Formula: C12H16N2O Molecular Formula: C12H16N2O Molecular Weight: 204.272 Type of Substance: heterocyclic InChI Key: SPCIYGNTAMCTRO-UHFFFAOYSA-N Note:

N OH

Substance Label (14) Label References 7

Furman, Svetlana; Nissim-Bardugo, Elinor; Zeeli, Shani; Weitman, Michal; Nudelman, Abraham; Finkin-Groner, Efrat; Moradov, Dorit; Shifrin, Helena; Schorer-Apelbaum, Donna; Weinstock, Marta; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 10; (2014); p. 2283 - 2287, View in Reaxys

Parker, Matthew A.; Kurrasch, Deborah M.; Nichols, David E.; Bioorganic and Medicinal Chemistry; vol. 16; nb. 8; (2008); p. 4661 - 4669, View in Reaxys; Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Casale, Rosario; Cautela, Domenico; Castaldo, Domenico; Journal of Agricultural and Food Chemistry; vol. 61; nb. 21; (2013); p. 5156 - 5162, View in Reaxys

Sard, Howard; Kumaran, Govindaraj; Morency, Cynthia; Roth, Bryan L.; Toth, Beth Ann; He, Ping; Shuster, Louis; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 20; (2005); p. 4555 - 4559, View in Reaxys

Yamada, Fumio; Tamura, Mayumi; Somei, Masanori; Heterocycles; vol. 49; nb. 1; (1998); p. 451 - 457, View in Reaxys; Sogawa, Kazuyo; Hashimoto, Kimiko; Shirahama, Haruhisa; Heterocycles; vol. 50; nb. 2; (1999); p. 657 - 660, View in Reaxys; Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 51; nb. 5; (1999); p. 1131 - 1135, View in Reaxys; Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 - 887, View in Reaxys

Yamada, Fumio; Tamura, Mayumi; Hasegawa, Atsuko; Somei, Masanori; Chemical and pharmaceutical bulletin; vol. 50; nb. 1; (2002); p. 92 - 99, View in Reaxys

Blair; Kurrasch-Orbaugh; Marona-Lewicka; Gumbay; Watts; Barker; Nichols; Journal of Medicinal Chemistry; vol. 43; nb. 24; (2000); p. 4701 - 4710, View in Reaxys

Nichols, David E.; Frescas, Stewart; Synthesis; nb. 6; (1999); p. 935 - 938, View in Reaxys

4-OH-DMT

Gerasimov, Madina; Marona-Lewicka, Danuta; Kurrasch-Orbaugh, Deborah M.; Qandil, Amjad M.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 42; nb. 20; (1999); p. 4257 - 4263, View in Reaxys

Merck 8110

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys

Patent; Sandoz Ltd.; US3075992; (1958); Chem.Abstr.; vol. 61; nb. 5613e; (1964), View in Reaxys; Migliaccio; Shieh; Byrn; Hathaway; Nichols; Journal of Medicinal Chemistry; vol. 24; nb. 2; (1981); p. 206 - 209, View in Reaxys

12a

Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys; Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys

VIII

Adron Harris; Homfeld; Campaigne; Journal of Pharmacy and Pharmacology; vol. 33; nb. 5; (1981); p. 320 - 322, View in Reaxys

Kuhnert-Brandstaetter et al.; Pharmaceutica Acta Helvetiae; vol. 50; (1975); p. 360,364, View in Reaxys

Patent; Sandoz Ltd.; GB912715; (1958); Chem.Abstr.; vol. 58; nb. 12516; (1963), View in Reaxys

Derivative (1) Comment (Derivative)

References

Oxalat: F: 239-240grad

Patent; Sandoz Ltd.; GB912715; (1958); Chem.Abstr.; vol. 58; nb. 12516; (1963), View in Reaxys

Melting Point (8) 1 of 8

Melting Point [°C]

173 - 176

Hu, Chunmei; Qin, Hua; Cui, Yuxin; Jia, Yanxing; Tetrahedron; vol. 65; nb. 45; (2009); p. 9075 - 9080, View in Reaxys 2 of 8

Melting Point [°C]

161

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Kuhnert-Brandstaetter et al.; Pharmaceutica Acta Helvetiae; vol. 50; (1975); p. 360,364, View in Reaxys; Kuhnert-Brandstaetter; Heindl; Archiv der Pharmazie (Weinheim, Germany); vol. 309; (1976); p. 625,627,628,630, View in Reaxys 3 of 8

Melting Point [°C]

170 - 173

Kuhnert-Brandstaetter; Heindl; Archiv der Pharmazie (Weinheim, Germany); vol. 309; (1976); p. 625,627,628,630, View in Reaxys 4 of 8

Melting Point [°C]

174

Kuhnert-Brandstaetter et al.; Pharmaceutica Acta Helvetiae; vol. 50; (1975); p. 360,364, View in Reaxys 5 of 8

Melting Point [°C]

173

Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys 6 of 8

Melting Point [°C]

172

Julia; Ricalens; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 269; (1969); p. 51, View in Reaxys 7 of 8

Melting Point [°C]

173 - 176

Patent; Sandoz; US3078214; (1963); Chem.Abstr.; vol. 59; nb. 8707a; (1963), View in Reaxys; Patent; Sandoz Ltd.; US3075992; (1958); Chem.Abstr.; vol. 61; nb. 5613e; (1964), View in Reaxys; Patent; Sandoz Ltd.; GB912715; (1958); Chem.Abstr.; vol. 58; nb. 12516; (1963), View in Reaxys; Patent; Sandoz Ltd.; DE1087321; Chem.Abstr.; nb. 27768; (1961), View in Reaxys 8 of 8

Melting Point [°C]

173 - 176

Solvent (Melting Point)

methanol; ethyl acetate

Hoffmann et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 1557,1563,1570, View in Reaxys; Troxler et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 2073,2098, View in Reaxys Density (1) 1 of 1

Density [g·cm-3]

1.19

Type (Density)

crystallographic

Petcher; Weber; J.C.S.; Perkin II 1974 946, View in Reaxys Chromatographic Data (1) Chromatographic References data LC (Liquid chromatography)

Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Casale, Rosario; Cautela, Domenico; Castaldo, Domenico; Journal of Agricultural and Food Chemistry; vol. 61; nb. 21; (2013); p. 5156 - 5162, View in Reaxys

Conformation (1) Object of Investi- References gation Conformation

Migliaccio; Shieh; Byrn; Hathaway; Nichols; Journal of Medicinal Chemistry; vol. 24; nb. 2; (1981); p. 206 - 209, View in Reaxys

Crystal Phase (3) Description (Crys- Comment (Crystal References tal Phase) Phase) Crystal structure determination

Petcher; Weber; J.C.S.; Perkin II 1974 946, View in Reaxys; Petcher; Weber; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1974); p. 946, View in Reaxys

Solid state structure properties

Petcher; Weber; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1974); p. 946, View in Reaxys

Crystal structure determination

β=91.3 grad, a=10.6 Angstroem, b=8.53 Angstroem, c=12.51 Angstroem, n=4.

Petcher; Weber; J.C.S.; Perkin II 1974 946, View in Reaxys

Crystal Property Description (2) Colour & Other References Properties

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yellow

Bartolucci, Silvia; Mari, Michele; Di Gregorio, Giovanni; Piersanti, Giovanni; Tetrahedron; vol. 72; nb. 18; (2016); p. 2233 - 2238, View in Reaxys

white

Manevski, Nenad; Kurkela, Mika; Hoeglund, Camilla; Mauriala, Timo; Court, Michael H.; Yli-Kauhaluoma, Jari; Finel, Moshe; Drug Metabolism and Disposition; vol. 38; nb. 3; (2010); p. 386 - 395, View in Reaxys

Crystal System (1) Crystal System References monoclinic

Petcher; Weber; J.C.S.; Perkin II 1974 946, View in Reaxys

Dissociation Exponent (1) 1 of 1

Dissociation Exponent (pK)

8.47

Dissociation Group

Temperature (Dissociation Exponent) [°C]

Solvent (Dissociation Exponent)

H2O

Method (Dissociation Exponent)

potentiometric

Type (Dissociation Exponent)

a1/apparent

Migliaccio; Shieh; Byrn; Hathaway; Nichols; Journal of Medicinal Chemistry; vol. 24; nb. 2; (1981); p. 206 - 209, View in Reaxys Interatomic Distances and Angles (1) Description Comment (Intera- References tomic Distances and Angles) Interatomic distances and angles

Roentgen-Diagramm.

Petcher; Weber; J.C.S.; Perkin II 1974 946, View in Reaxys

Liquid/Liquid Systems (MCS) (1) 1 of 1

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Partner (Liquid/Liquid Systems (MCS))

octanol; H2O

Migliaccio; Shieh; Byrn; Hathaway; Nichols; Journal of Medicinal Chemistry; vol. 24; nb. 2; (1981); p. 206 - 209, View in Reaxys Liquid/Solid Systems (MCS) (1) 1 of 1

Description (Liquid/Solid Eutectic Systems (MCS)) Kuhnert-Brandstaetter et al.; Pharmaceutica Acta Helvetiae; vol. 50; (1975); p. 360,364, View in Reaxys

Solubility (MCS) (1) 1 of 1

Comment (Solubility (MCS))

in verd. aq. Saeuren loesl.

Patent; Sandoz Ltd.; DE1087321; Chem.Abstr.; nb. 27768; (1961), View in Reaxys Space Group (1) Space Group

References

14; 14

Petcher; Weber; J.C.S.; Perkin II 1974 946, View in Reaxys

NMR Spectroscopy (14) 1 of 14

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy)

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Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

Location

supporting information

Signals [ppm]

2.39; 2.71 - 2.73; 2.95 - 2.97; 6.58; 6.84; 6.87; 7.04 - 7.08; 8.03

Kind of signal

s, 6H; m, 2H; m, 2H; dd, 1H, J&1%=0.5, J&2%=7.5 Hz; d, 1H, J=2.0 Hz; dd, 1H, J&1%=0.5, J&2%=8.0 Hz; m, 1H; brs, 1H

NMR (400 MHz, CDCl3): δ 2.39 (s, 6H), 2.71-2.73 (m, 2H), 2.95-2.97 (m, 2H), 6.58 (dd, 1H, J1=0.5, J2=7.5 Hz), 6.84 (d, 1H, J=2.0 Hz), 6.87 (dd, 1H, J1=0.5, J2=8.0 Hz), 7.04-7.08 (m, 1H), 8.03 (brs, 1H)

Bartolucci, Silvia; Mari, Michele; Di Gregorio, Giovanni; Piersanti, Giovanni; Tetrahedron; vol. 72; nb. 18; (2016); p. 2233 - 2238, View in Reaxys 2 of 14

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Original Text (NMR Spectroscopy)

13C NMR (100 MHz, CDCl ): δ 25.1, 45.3, 61.6, 102.5, 106.4, 114.4, 117.5, 120.9, 123.5, 3 139.1, 152.1

Location

supporting information

Signals [ppm]

25.1; 45.3; 61.6; 102.5; 106.4; 114.4; 117.5; 120.9; 123.5; 139.1; 152.1

Bartolucci, Silvia; Mari, Michele; Di Gregorio, Giovanni; Piersanti, Giovanni; Tetrahedron; vol. 72; nb. 18; (2016); p. 2233 - 2238, View in Reaxys 3 of 14

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Hu, Chunmei; Qin, Hua; Cui, Yuxin; Jia, Yanxing; Tetrahedron; vol. 65; nb. 45; (2009); p. 9075 - 9080, View in Reaxys 4 of 14

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Hu, Chunmei; Qin, Hua; Cui, Yuxin; Jia, Yanxing; Tetrahedron; vol. 65; nb. 45; (2009); p. 9075 - 9080, View in Reaxys 5 of 14

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

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Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Comment (NMR Spectroscopy)

ambient temperature

Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 887, View in Reaxys 6 of 14

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Comment (NMR Spectroscopy)

ambient temperature

Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 887, View in Reaxys 7 of 14

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Comment (NMR Spectroscopy)

ambient temperature

Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 887, View in Reaxys 8 of 14

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Nichols, David E.; Frescas, Stewart; Synthesis; nb. 6; (1999); p. 935 - 938, View in Reaxys 9 of 14

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 51; nb. 5; (1999); p. 1131 - 1135, View in Reaxys 10 of 14

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 51; nb. 5; (1999); p. 1131 - 1135, View in Reaxys 11 of 14

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Yamada, Fumio; Tamura, Mayumi; Somei, Masanori; Heterocycles; vol. 49; nb. 1; (1998); p. 451 - 457, View in Reaxys 12 of 14

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Migliaccio; Shieh; Byrn; Hathaway; Nichols; Journal of Medicinal Chemistry; vol. 24; nb. 2; (1981); p. 206 - 209, View in Reaxys 13 of 14

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Migliaccio; Shieh; Byrn; Hathaway; Nichols; Journal of Medicinal Chemistry; vol. 24; nb. 2; (1981); p. 206 - 209, View in Reaxys 14 of 14

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Migliaccio; Shieh; Byrn; Hathaway; Nichols; Journal of Medicinal Chemistry; vol. 24; nb. 2; (1981); p. 206 - 209, View in Reaxys IR Spectroscopy (5) 1 of 5

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 887, View in Reaxys 2 of 5

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 51; nb. 5; (1999); p. 1131 - 1135, View in Reaxys 3 of 5

Description (IR Spectroscopy)

Bands

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Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3250 - 480 1/cm

Yamada, Fumio; Tamura, Mayumi; Somei, Masanori; Heterocycles; vol. 49; nb. 1; (1998); p. 451 - 457, View in Reaxys 4 of 5

Description (IR Spectroscopy)

Kuhnert-Brandstaetter; Heindl; Archiv der Pharmazie (Weinheim, Germany); vol. 309; (1976); p. 625,627,628,630, View in Reaxys 5 of 5

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

4000 - 625 cm**(-1)

Hoffmann et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 1557,1563,1570, View in Reaxys Mass Spectrometry (5) Description (Mass Peak Spectrometry) electrospray ionisation (ESI); spectrum

205 m/z

References Bartolucci, Silvia; Mari, Michele; Di Gregorio, Giovanni; Piersanti, Giovanni; Tetrahedron; vol. 72; nb. 18; (2016); p. 2233 - 2238, View in Reaxys

liquid chromatography mass spectrometry (LCMS); electrospray ionisation (ESI); tandem mass spectrometry; spectrum

ESI (Electrospray ionisation); Spectrum

Hu, Chunmei; Qin, Hua; Cui, Yuxin; Jia, Yanxing; Tetrahedron; vol. 65; nb. 45; (2009); p. 9075 - 9080, View in Reaxys

spectrum

Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 - 887, View in Reaxys Bellman; Journal - Association of Official Analytical Chemists; vol. 51; (1968); p. 164,169, View in Reaxys

UV/VIS Spectroscopy (4) 1 of 4

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 222.5; 268; 284.5; 294 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

35481.3; 5248.07; 4168.69; 3801.89

Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 887, View in Reaxys 2 of 4

Description (UV/VIS Spectroscopy)

Absorption maxima

Kuhnert-Brandstaetter et al.; Pharmaceutica Acta Helvetiae; vol. 50; (1975); p. 360,364, View in Reaxys 3 of 4

Description (UV/VIS Spectroscopy)

UV/VIS

Kuhnert-Brandstaetter et al.; Pharmaceutica Acta Helvetiae; vol. 50; (1975); p. 360,364, View in Reaxys; Patent; Sandoz Ltd.; DE1087321; Chem.Abstr.; nb. 27768; (1961), View in Reaxys

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4 of 4

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

methanol

Comment (UV/VIS Spectroscopy)

210 - 300 nm

Hoffmann et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 1557,1563,1570, View in Reaxys; Troxler et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 2073,2098, View in Reaxys Fluorescence Spectroscopy (1) Description (Fluo- References rescence Spectroscopy) Fluorescence

Bridges; Williams; Biochemical Journal; vol. 107; (1968); p. 225,228, View in Reaxys; Aaron et al.; Clinica Chimica Acta; vol. 45; (1973); p. 375,379, View in Reaxys

Phosphorescence Spectroscopy (1) Description References (Phosphorescence Spectroscopy) Phosphorescence Aaron et al.; Clinica Chimica Acta; vol. 45; (1973); p. 375,379, View in Reaxys Pharmacological Data (25) 1 of 25

Comment (Pharmacological Data)

Bioactivities present

Patent; Day, Brian J.; Velsor, Leonard W.; US2004/87527; (2004); (A1) English, View in Reaxys; Hoffmann et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 1557,1563,1570, View in Reaxys; Troxler et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 2073,2098, View in Reaxys; Petcher; Weber; J.C.S.; Perkin II 1974 946, View in Reaxys; Bridges; Williams; Biochemical Journal; vol. 107; (1968); p. 225,228, View in Reaxys; Kuhnert-Brandstaetter et al.; Pharmaceutica Acta Helvetiae; vol. 50; (1975); p. 360,364, View in Reaxys; Patent; Sandoz; US3078214; (1963); Chem.Abstr.; vol. 59; nb. 8707a; (1963), View in Reaxys; Patent; Sandoz Ltd.; US3075992; (1958); Chem.Abstr.; vol. 61; nb. 5613e; (1964), View in Reaxys; Patent; Sandoz Ltd.; GB912715; (1958); Chem.Abstr.; vol. 58; nb. 12516; (1963), View in Reaxys; Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys; Julia; Ricalens; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 269; (1969); p. 51, View in Reaxys; Bellman; Journal - Association of Official Analytical Chemists; vol. 51; (1968); p. 164,169, View in Reaxys; Aaron et al.; Clinica Chimica Acta; vol. 45; (1973); p. 375,379, View in Reaxys; Kuhnert-Brandstaetter; Heindl; Archiv der Pharmazie (Weinheim, Germany); vol. 309; (1976); p. 625,627,628,630, View in Reaxys; Petcher; Weber; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1974); p. 946, View in Reaxys; Julia; Ricalens; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 275; (1972); p. 613, View in Reaxys; Agurell; Nilsson; Tetrahedron letters; vol. 9; (1968); p. 1063 - 1064, View in Reaxys; Hofmann et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 257; (1963); p. 10, View in Reaxys; Patent; Sandoz Ltd.; DE1087321; Chem.Abstr.; nb. 27768; (1961), View in Reaxys; Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys; Migliaccio; Shieh; Byrn; Hathaway; Nichols; Journal of Medicinal Chemistry; vol. 24; nb. 2; (1981); p. 206 - 209, View in Reaxys; Laubscher; Pletscher; Journal of Pharmacy and Pharmacology; vol. 32; nb. 8; (1980); p. 601 - 602, View in Reaxys; Adron Harris; Homfeld; Campaigne; Journal of Pharmacy and Pharmacology; vol. 33; nb. 5; (1981); p. 320 - 322, View in Reaxys; Yamada, Fumio; Tamura, Mayumi; Somei, Masanori; Heterocycles; vol. 49; nb. 1; (1998); p. 451 - 457, View in Reaxys; Sogawa, Kazuyo; Hashimoto, Kimiko; Shirahama, Haruhisa; Heterocycles; vol. 50; nb. 2; (1999); p. 657 - 660, View in Reaxys; Nichols, David E.; Frescas, Stewart; Synthesis; nb. 6; (1999); p. 935 - 938, View in Reaxys; Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 51; nb. 5; (1999); p. 1131 - 1135, View in Reaxys; Gerasimov, Madina; Marona-Lewicka, Danuta; Kurrasch-Orbaugh, Deborah M.; Qandil, Amjad M.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 42; nb. 20; (1999); p. 4257 - 4263, View in Reaxys; Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys; Blair; Kurrasch-Orbaugh; Marona-Lewicka; Gumbay; Watts; Barker; Nichols; Journal of Medicinal Chemistry; vol. 43; nb. 24; (2000); p. 4701 - 4710, View in Reaxys; Yamada, Fumio; Tamura, Mayumi; Hasegawa, Atsuko; Somei, Masanori; Chemical and pharmaceutical bulletin; vol. 50; nb. 1; (2002); p. 92 - 99, View in Reaxys; Ebersole, Barbara J.; Visiers, Irache; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 63; nb. 1; (2003); p. 36 - 43, View in Reaxys; Chambers, James J.; Parrish, Jason C.; Jensen, Niels H.; Kurrasch-Orbaugh, Deborah M.; Marona-Lewicka, Danuta; Nichols, David E.; Journal of Medicinal Chemistry; vol. 46; nb. 16; (2003); p. 3526 - 3535, View in Reaxys; Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 - 887, View in Reaxys; Sard, Howard; Kumaran, Govindaraj; Morency, Cynthia; Roth, Bryan L.; Toth, Beth Ann; He, Ping; Shuster, Louis; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 20; (2005); p. 4555 - 4559, View in Reaxys; McLean, Thomas H.; Chambers, James J.; Parrish, Jason C.; Braden, Michael R.; Marona-Lewicka, Danuta; Kurrasch-Orbaugh, Deborah; Nichols, David E.; Journal of Medicinal Chemistry; vol. 49; nb. 14; (2006); p. 4269 - 4274, View in Reaxys; Parker, Matthew A.; Kurrasch, Deborah M.; Nichols, David E.; Bioorganic and Medicinal Chem-

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istry; vol. 16; nb. 8; (2008); p. 4661 - 4669, View in Reaxys; Patent; Bristol, David William; King, Clifford Riley; Mitchener, JR., Joseph Pike; Audia, Vicki Haynes; US2008/293695; (2008); (A1) English, View in Reaxys; Hu, Chunmei; Qin, Hua; Cui, Yuxin; Jia, Yanxing; Tetrahedron; vol. 65; nb. 45; (2009); p. 9075 - 9080, View in Reaxys; Manevski, Nenad; Kurkela, Mika; Hoeglund, Camilla; Mauriala, Timo; Court, Michael H.; YliKauhaluoma, Jari; Finel, Moshe; Drug Metabolism and Disposition; vol. 38; nb. 3; (2010); p. 386 - 395, View in Reaxys; Wu, Baojian; Wang, Xiaoqiang; Zhang, Shuxing; Hu, Ming; Pharmaceutical Research; vol. 29; nb. 6; (2012); p. 1544 - 1561, View in Reaxys; Rothman, Richard B.; Partilla, John S.; Baumann, Michael H.; Lightfoot-Siordia, Catrissa; Blough, Bruce E.; Journal of Pharmacology and Experimental Therapeutics; vol. 341; nb. 1; (2012); p. 251 - 262, View in Reaxys; Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Casale, Rosario; Cautela, Domenico; Castaldo, Domenico; Journal of Agricultural and Food Chemistry; vol. 61; nb. 21; (2013); p. 5156 - 5162, View in Reaxys; Daly; Creveling; Witkop; Journal of medicinal chemistry; vol. 9; nb. 3; (1966); p. 273 - 280, View in Reaxys; Lovell; Freedman; Molecular Pharmacology; vol. 12; nb. 4; (1976); p. 620 630, View in Reaxys; Kier; Hall; Journal of Medicinal Chemistry; vol. 20; nb. 12; (1977); p. 1631 - 1636, View in Reaxys; Peroutka; McCarthy; Guan; Life Sciences; vol. 49; nb. 6; (1991); p. 409 - 418, View in Reaxys; McKenna; Repke; Lo; Peroutka; Neuropharmacology; vol. 29; nb. 3; (1990); p. 193 - 198, View in Reaxys; Johnson; Mathis; Shulgin; Hoffman; Nichols; Pharmacology, biochemistry, and behavior; vol. 35; nb. 1; (1990); p. 211 - 217, View in Reaxys; McKenna; Peroutka; The Journal of neuroscience : the official journal of the Society for Neuroscience; vol. 9; nb. 10; (1989); p. 3482 - 3490, View in Reaxys; Glennon; Young; Rosecrans; Kallman; Psychopharmacology; vol. 68; nb. 2; (1980); p. 155 - 158, View in Reaxys; Glennon; Gessner; Journal of Medicinal Chemistry; vol. 22; nb. 4; (1979); p. 428 - 432, View in Reaxys; Dyer, D C; Gant, D W; The Journal of pharmacology and experimental therapeutics; vol. 184; nb. 2; (1973); p. 366 - 75, View in Reaxys; ROBERT G. TABORSKY; PETER DELVIGS; DJURO PALAIC; MERLIN BUMPUS; Journal of medicinal chemistry; vol. 10; nb. 3; (1967); p. 403 - 407, View in Reaxys; SHEILA M. BOCKS; Phytochemistry; vol. 6; nb. 12; (1967); p. 1629 - 1631, View in Reaxys; Psychotropic Drugs and Related Compounds, 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972; (1972), View in Reaxys; USDIN E; AMAI RL; Psychopharmacology bulletin; vol. 2; (1963); p. 17 - 93, View in Reaxys; Furman, Svetlana; Nissim-Bardugo, Elinor; Zeeli, Shani; Weitman, Michal; Nudelman, Abraham; Finkin-Groner, Efrat; Moradov, Dorit; Shifrin, Helena; Schorer-Apelbaum, Donna; Weinstock, Marta; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 10; (2014); p. 2283 - 2287, View in Reaxys; Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys; Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127556; (2015); (A1) English, View in Reaxys; Bartolucci, Silvia; Mari, Michele; Di Gregorio, Giovanni; Piersanti, Giovanni; Tetrahedron; vol. 72; nb. 18; (2016); p. 2233 - 2238, View in Reaxys 2 of 25

Comment (Pharmacological Data)

physiological behaviour discussed

Effect (Pharmacological Data)

5-hydroxytryptamine transporter-mediated release; effect on

Species or Test-System (Pharmacological Data)

brain synaptosomes of Sprague-Dawley rat

Sex

male

Further Details (Pharmacological Data)

transporter-mediated release assay; radioligand: 5 nM [3H]5-hydroxytryptamine; synaptosomal preparation from whole brain minus cerebellum and caudate used

Results

molecular target: rat 5-hydroxytryptamine transporter

Rothman, Richard B.; Partilla, John S.; Baumann, Michael H.; Lightfoot-Siordia, Catrissa; Blough, Bruce E.; Journal of Pharmacology and Experimental Therapeutics; vol. 341; nb. 1; (2012); p. 251 - 262, View in Reaxys 4 of 25

Effect (Pharmacological Data)

5-hydroxytryptamine transporter-mediated release; effect on

Species or Test-System (Pharmacological Data)

brain synaptosomes of Sprague-Dawley rat

Sex

male

Further Details (Pharmacological Data)

transporter-mediated release assay; radioligand: 5 nM [3H]5-hydroxytryptamine; synaptosomal preparation from whole brain minus cerebellum and caudate used; effective concentration (EC)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

561 nmol/l

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5 of 25

Effect (Pharmacological Data)

5-hydroxytryptamine transporter-mediated release; effect on

Species or Test-System (Pharmacological Data)

brain synaptosomes of Sprague-Dawley rat

Sex

male

Further Details (Pharmacological Data)

transporter-mediated release assay; radioligand: 5 nM [3H]5-hydroxytryptamine; synaptosomal preparation from whole brain minus cerebellum and caudate used; maximal release rate (Emax)

Type (Pharmacological Data)

Emax

Value of Type (Pharmacological Data)

54 percent

Effect (Pharmacological Data)

dopamine transporter-mediated release; effect on

Species or Test-System (Pharmacological Data)

brain synaptosomes of Sprague-Dawley rat

Sex

male

Further Details (Pharmacological Data)

transporter-mediated release assay; radioligand: 5 nM [3H]1-methyl-4-phenylpyridinium; synaptosomal preparation from caudate used; effective concentration (EC)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

> 10000 nmol/l

Effect (Pharmacological Data)

norepinephrine transporter-mediated release; effect on

Species or Test-System (Pharmacological Data)

brain synaptosomes of Sprague-Dawley rat

Sex

male

Further Details (Pharmacological Data)

transporter-mediated release assay; radioligand: 5 nM [3H]1-methyl-4-phenylpyridinium; synaptosomal preparation from whole brain minus cerebellum and caudate used; effective concentration (EC)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

> 10000 nmol/l

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

brain frontal cortex homogenate of Sprague-Dawley rat

Sex

male

Method (Pharmacological Data)

5-HT2A receptor binding assay; tissue homogenate, <3H>MDL 100,907 and title comp. incub. for 15 min at 37 deg C in a shaking water bath; vacuum filtration performed; radioactivity measured using liquid scintillation spectroscopy at 37percent efficiency

Further Details (Pharmacological Data)

non-specific binding was determined in the presence of cinanserin (10 μM); Ki: binding affinity

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Type (Pharmacological Data)

Value of Type (Pharmacological Data)

323 nmol/l

Parker, Matthew A.; Kurrasch, Deborah M.; Nichols, David E.; Bioorganic and Medicinal Chemistry; vol. 16; nb. 8; (2008); p. 4661 - 4669, View in Reaxys 9 of 25

Effect (Pharmacological Data)

functional activity

Species or Test-System (Pharmacological Data)

rat

Method (Pharmacological Data)

drug discrimination assay using rats trained to distinguish the 5-HT2A receptor agonist LSD from saline; rat behavior observed

Results

title comp. indirectly determined to be an agonist of 5-HT2A receptor

Parker, Matthew A.; Kurrasch, Deborah M.; Nichols, David E.; Bioorganic and Medicinal Chemistry; vol. 16; nb. 8; (2008); p. 4661 - 4669, View in Reaxys 10 of 25

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

cells expressing 5-HT2A receptor

Method (Pharmacological Data)

phosphoinositide hydrolysis assay; <3H>inositol-loaded cells; modified Krebs-biscarbonate buffer

Further Details (Pharmacological Data)

activation of phosphoinositide hydrolysis expressed relative to serotonin at 100 percent

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

24 nmol/l

Results

title comp. showed 43 percent receptor activation

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

cells expressing 5-HT2B receptor

Method (Pharmacological Data)

phosphoinositide hydrolysis assay; <3H>inositol-loaded cells; modified Krebs-biscarbonate buffer

Further Details (Pharmacological Data)

activation of phosphoinositide hydrolysis expressed relative to serotonin at 100 percent

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

58 nmol/l

Results

title comp. showed 45 percent receptor activation

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

cells expressing 5-HT2C receptor

Method (Pharmacological Data)

phosphoinositide hydrolysis assay; <3H>inositol-loaded cells; modified Krebs-biscarbonate buffer

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Further Details (Pharmacological Data)

activation of phosphoinositide hydrolysis expressed relative to serotonin at 100 percent

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

30 nmol/l

Results

title comp. showed 51 percent receptor activation

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

Swiss-Webster mouse

Sex

male

Concentration (Pharmacological Data)

0.5 mg

Kind of Dosing (Pharmacological Data)

injected in saline + ascorbic acid 5 min prior to serotonin administration

Method (Pharmacological Data)

5 mice (4-6 weeks old, 25-45 g) injected sc to the rostral back with 0.1 ml of 0.4 mg/ml of serotonin in saline solution with ascorbic acid; cumulative number of scratches recorded every 5 min for 30 min

Further Details (Pharmacological Data)

inhibition of serotonin-induced scratching evaluated

Results

title comp. inhibited scratching

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

NIH3T3 fibroblasts expressing rat 5-HT2A receptors

Method (Pharmacological Data)

in vitro; effect on phosphoinositol (IP) hydrolysis evaluated; cells prelabeled with <3H>myo-inositol; CRML-1066 medium; 37 deg C; pretreated for 15 min with 10 μmol/l pargyline and 10 μmol/l LiCl

Further Details (Pharmacological Data)

then title comp. added and incubation followed for further 30 min; accumulation of inositol phosphates determined; liquid scintillation counting; intrinsic activity: percent response given by title comp. compared with response produced by 10 μmol/l serotonin

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

2310 nmol/l

Results

intrinsic activity: 52percent

Blair; Kurrasch-Orbaugh; Marona-Lewicka; Gumbay; Watts; Barker; Nichols; Journal of Medicinal Chemistry; vol. 43; nb. 24; (2000); p. 4701 - 4710, View in Reaxys 15 of 25

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

CHO cells expressing human 5-HT1A receptors

Method (Pharmacological Data)

in vitro; competition binding assay; 0.80 nmol/l <3H>8-OH-DPAT (spec. act.: 124 Ci/mmol) used as radioligand; assay buffer, pH 7.4; 25 deg C; incubated for 60 min; liquid scintillation counting; nonspecific binding determined with 10 μmol/l serotonin

Further Details (Pharmacological Data)

DOI: 2,5-dimethoxy-4-iodoamphetamine

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Type (Pharmacological Data)

Value of Type (Pharmacological Data)

49 nmol/l

Blair; Kurrasch-Orbaugh; Marona-Lewicka; Gumbay; Watts; Barker; Nichols; Journal of Medicinal Chemistry; vol. 43; nb. 24; (2000); p. 4701 - 4710, View in Reaxys 16 of 25

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

NIH3T3 fibroblast expressing rat 5-HT2C receptors

Method (Pharmacological Data)

in vitro; competition binding assay; 0.20 nmol/l <125I>DOI (spec. act.: 2200 Ci/mmol) used as radioligand; assay buffer, pH 7.4; 25 deg C; incubated for 60 min; liquid scintillation counting; nonspecific binding determined with 10 μmol/l mianserin

Further Details (Pharmacological Data)

DOI: 2,5-dimethoxy-4-iodoamphetamine

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

10 nmol/l

Blair; Kurrasch-Orbaugh; Marona-Lewicka; Gumbay; Watts; Barker; Nichols; Journal of Medicinal Chemistry; vol. 43; nb. 24; (2000); p. 4701 - 4710, View in Reaxys 17 of 25

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

NIH3T3 fibroblast expressing rat 5-HT2A receptors

Method (Pharmacological Data)

Further Details (Pharmacological Data)

DOI: 2,5-dimethoxy-4-iodoamphetamine

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

25 nmol/l

Blair; Kurrasch-Orbaugh; Marona-Lewicka; Gumbay; Watts; Barker; Nichols; Journal of Medicinal Chemistry; vol. 43; nb. 24; (2000); p. 4701 - 4710, View in Reaxys 18 of 25

Effect (Pharmacological Data)

psychotomimetic

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Kind of Dosing (Pharmacological Data)

administered 30 min prior to session

Method (Pharmacological Data)

in vivo; hallucinogenic-like activity evaluated in two-lever drug discrimination behavioral assay in LSD-trained rats; 8-12 rats (200-220 g) trained to discriminate LSD tartrate (0.08 mg/kg i.p.) from saline; number of presses on one lever monitored

Further Details (Pharmacological Data)

percent of rats selecting title comp. lever (percentSDL) for each dose determined; LSD and DOI (ED50: 0.037 and 0.27 μmol/kg, respectively) used as positive controls; LSD: (+)lysergic acid diethylamide; DOI: 2,5-dimethoxy-4-iodoamphetamine

Type (Pharmacological Data)

ED50

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Value of Type (Pharmacological Data)

1.01 μmol/kg

Results

title comp. fully substituted in LSD-trained rats (percentSDL >= 80percent)

Blair; Kurrasch-Orbaugh; Marona-Lewicka; Gumbay; Watts; Barker; Nichols; Journal of Medicinal Chemistry; vol. 43; nb. 24; (2000); p. 4701 - 4710, View in Reaxys 19 of 25

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat cortical homogenate

Sex

male

Method (Pharmacological Data)

in vitro; affinity at 5-HT2A receptor assayed using radioligand competition binding assay; frontal cortices dissected from rat brains; <3H>ketanserin; Te Pac buffer; 37 deg C; 15min incubation; liquid scintillation spectroscopy

Type (Pharmacological Data)

K0.5

Value of Type (Pharmacological Data)

390 nmol/l

Gerasimov, Madina; Marona-Lewicka, Danuta; Kurrasch-Orbaugh, Deborah M.; Qandil, Amjad M.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 42; nb. 20; (1999); p. 4257 - 4263, View in Reaxys 20 of 25

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

mutant A5.46S 5-HT2C receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharmacological Data)

Ki: binding affinity

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

73 nmol/l

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 21 of 25

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

wild-type 5-HT2C receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharmacological Data)

Ki: binding affinity

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

140 nmol/l

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 22 of 25

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

mutant S5.46A 5-HT2A receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

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Further Details (Pharmacological Data)

Ki: binding affinity

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

259 nmol/l

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 23 of 25

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

wild-type 5-HT2A receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharmacological Data)

Ki: binding affinity

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

81 nmol/l

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 24 of 25

Comment (Pharmacological Data)

hallucinogenic activity; ED 50: 4 μmol/kg (rats, intraperitoneally)

Adron Harris; Homfeld; Campaigne; Journal of Pharmacy and Pharmacology; vol. 33; nb. 5; (1981); p. 320 - 322, View in Reaxys 25 of 25

Comment (Pharmacological Data)

markedly increases the cyclic GMP content in human blood platelets

Laubscher; Pletscher; Journal of Pharmacy and Pharmacology; vol. 32; nb. 8; (1980); p. 601 - 602, View in Reaxys Use (13) Laboratory Use and Handling

Use Pattern

Location

References

Parkinson's disease (PD)

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Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

Pharmaceuticals

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Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

inducing or facilitating micturition in combination with 5-HT1A receptor agonist, 5HT1A/7 receptor agonist, cholinesterase inhibitor, NMDA receptor agonist, noradrenaline/dopamine precursor

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Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

multiple sclerosis (MS)

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Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

spinal cord injury (SCI)

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Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

urinary retention

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Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

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Pharmaceuticals

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Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127556; (2015); (A1) English, View in Reaxys

facilitating defeca- Page/Page coltion or acute defe- umn 20; 21; 22; cation in a subject 23 in combination with a cholinesterase inhibitor; a 5HT1A receptor agonist; a 5HT1A/7 receptor agonist; and a beta-2 adrenergic receptor agonist

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127556; (2015); (A1) English, View in Reaxys

inducing defecaPage/Page coltion or acute defe- umn 20; 21; 22; cation in a subject 23 in combination with a cholinesterase inhibitor; a 5HT1A receptor agonist; a 5HT1A/7 receptor agonist; and a beta-2 adrenergic receptor agonist

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127556; (2015); (A1) English, View in Reaxys

store in the dark

store under inert gas

store cold

Patent; Bristol, David William; King, Clifford Riley; Mitchener, JR., Joseph Pike; Audia, Vicki Haynes; US2008/293695; (2008); (A1) English, View in Reaxys

Isolation from Natural Product (3) Isolation from References Natural Product V.: im europ. Hofmann et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 257; Champignon (Psi- (1963); p. 10, View in Reaxys locybe semilanceata Fr.) Schimmelpilz-Kul- Patent; Sandoz Ltd.; DE1087321; Chem.Abstr.; nb. 27768; (1961), View in Reaxys turen Isolierung aus Hoffmann et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 1557,1563,1570, View in Reaxys Psilocybe mexicana

Reaxys ID 5200143 View in Reaxys

2/7

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Chemical Name: psilocin monooxalate Linear Structure Formula: C12H16N2O*C2H2O4 Molecular Formula: C2H2O4*C12H16N2O Molecular Weight: 294.307 Type of Substance: heterocyclic InChI Key: FZWCNXDYYDPWJJ-UHFFFAOYSA-N Note:

N HO

Substance Label (1) Label References II*C2H2O4

Migliaccio; Shieh; Byrn; Hathaway; Nichols; Journal of Medicinal Chemistry; vol. 24; nb. 2; (1981); p. 206 - 209, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- D2O scopy) Migliaccio; Shieh; Byrn; Hathaway; Nichols; Journal of Medicinal Chemistry; vol. 24; nb. 2; (1981); p. 206 - 209, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- D2O scopy) Comment (NMR Spectroscopy)

1H-1H

Migliaccio; Shieh; Byrn; Hathaway; Nichols; Journal of Medicinal Chemistry; vol. 24; nb. 2; (1981); p. 206 - 209, View in Reaxys

Reaxys ID 8146739 View in Reaxys

3/7 11CH

Chemical Name: [11C]psilocin Linear Structure Formula: C11 (11)CH16N2O Molecular Formula: C12H16N2O Molecular Weight: 203.261 Type of Substance: heterocyclic InChI Key: SPCIYGNTAMCTRO-BJUDXGSMSA-N Note:

Substance Label (1) Label References 5

Ametamey; Vollenweider; Patt; Bourquin; Hasler; Beer; Schubiger; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 41; nb. 7; (1998); p. 585 - 594, View in Reaxys

Reaxys ID 8146740 View in Reaxys

4/7 Chemical Name: [13C]psilocin Linear Structure Formula: C11 (13)CH16N2O Molecular Formula: C12H16N2O Molecular Weight: 205.261 Type of Substance: heterocyclic InChI Key: SPCIYGNTAMCTRO-OUBTZVSYSA-N Note:

CH 3

NMR Spectroscopy (1)

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1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- D2O scopy) Frequency (NMR Spectroscopy) [MHz]

Ametamey; Vollenweider; Patt; Bourquin; Hasler; Beer; Schubiger; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 41; nb. 7; (1998); p. 585 - 594, View in Reaxys

Reaxys ID 8263770 View in Reaxys

5/7 Linear Structure Formula: C12H15DN2O Molecular Formula: C12H16N2O Molecular Weight: 205.264 Type of Substance: heterocyclic InChI Key: SPCIYGNTAMCTRO-UICOGKGYSA-N Note:

N OH 2H

Substance Label (1) Label References 1 (C5-D)

Sogawa, Kazuyo; Hashimoto, Kimiko; Shirahama, Haruhisa; Heterocycles; vol. 50; nb. 2; (1999); p. 657 660, View in Reaxys

Reaxys ID 10614427 View in Reaxys

N OH

6/7

Chemical Name: Psilocin maleate Linear Structure Formula: C12H16N2O*C4H4O4 Molecular Formula: C4H4O4*C12H16N2O Molecular Weight: 320.345 Type of Substance: heterocyclic InChI Key: IMHPPLRYVLGYIO-BTJKTKAUSA-N Note:

Z O

Pharmacological Data (4) 1 of 4

Comment (Pharmacological Data)

Bioactivities present

Braden, Michael R.; Parrish, Jason C.; Naylor, John C.; Nichols, David E.; Molecular Pharmacology; vol. 70; nb. 6; (2006); p. 1956 - 1964, View in Reaxys 2 of 4

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing human 5-HT2A receptor

Method (Pharmacological Data)

competition binding assay for ability of title comp. to displace (+/-)-<125I>-DOI ((+/-)<125I>-4-iodo-2,5-dimethoxyphenylisopropylamine; 0.25 nmol/l)

Further Details (Pharmacological Data)

HEK: human embryonic kidney; positive control: 5-hydroxytryptamine (5-HT), Ki value of 4.84 nmol/l

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

11.8 nmol/l

Braden, Michael R.; Parrish, Jason C.; Naylor, John C.; Nichols, David E.; Molecular Pharmacology; vol. 70; nb. 6; (2006); p. 1956 - 1964, View in Reaxys

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3 of 4

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing human 5-HT2A receptor

Method (Pharmacological Data)

competition binding assay for ability of title comp. to displace <3H>ketanserin (10 nmol/l)

Further Details (Pharmacological Data)

HEK: human embryonic kidney; positive control: 5-hydroxytryptamine (5-HT), Ki value of 4.84 nmol/l

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

22.8 nmol/l

Braden, Michael R.; Parrish, Jason C.; Naylor, John C.; Nichols, David E.; Molecular Pharmacology; vol. 70; nb. 6; (2006); p. 1956 - 1964, View in Reaxys 4 of 4

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

HEK-293 cells expressing human 5-HT2A receptor

Method (Pharmacological Data)

title comp. ability to stimulate hydrolysis of radiolabeled phosphatidylinositides assessed by measurement of radiolabeled inositol phosphate accumulation in cells

Further Details (Pharmacological Data)

HEK: human embryonic kidney; positive control: 5-hydroxytryptamine (5-HT), EC50 value of 5.17 nmol/l

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

7.29 nmol/l

Results

intrinsic activity was 105 percent

Braden, Michael R.; Parrish, Jason C.; Naylor, John C.; Nichols, David E.; Molecular Pharmacology; vol. 70; nb. 6; (2006); p. 1956 - 1964, View in Reaxys

Reaxys ID 24205093 View in Reaxys

7/7 -1 HCl

Chemical Name: Psilocine hydrochloride Linear Structure Formula: C12H16N2O*(x)ClH Molecular Formula: C12H16N2O*(x)ClH InChI Key: HLYRAUWFYBSTKD-UHFFFAOYSA-N Note:

N OH

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Whitaker; Seeman; Psychopharmacology; vol. 59; nb. 1; (1978); p. 1 - 5, View in Reaxys

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