Exploring Psilocin. To explore a different substance…

Names:
4-HO-DMT · PSOH · CX-59 · Psilocin · N,N-Dimethyl-4-hydroxytryptamine · 3-[2-(Dimethylamino)ethyl]-4-indolol · 4-Indolol, 3-[2-(dimethylamino)ethyl] · Tryptamine, 4-hydroxy-N,N-dimethyl
IUPAC name:
3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
ID: 5018 · Formula: C12H16N2O · Molecular weight: 204.268
InChI: InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3

Meyer, MR; Caspar, A; Brandt, SD; Maurer, HH. A qualitative/quantitative approach for the detection of 37 tryptamine-derived designer drugs, 5 β-carbolines, ibogaine, and yohimbine in human urine and plasma using standard urine screening and multi-analyte approaches. Anal. Bioanal. Chem., 1 Jan 2014, 406 (1), 225–237. 457 kB. http://dx.doi.org/10.1007/s00216-013-7425-9

Chilton, WS; Bigwood, J; Jensen, RE. Psilocin, Bufotenine and serotonin: Historical and biosynthetic observations. J. Psychoactive Drugs, 1 Jan 1979, 11 (1–2), 61–69. 9.5 MB. http://dx.doi.org/10.1080/02791072.1979.10472093

Troxler, F; Seemann, F; Hofmann, A. Abwandlungsprodukte von Psilocybin und Psilocin. 2. Mitteilung über synthetische Indolverbindungen. Helv. Chim. Acta, 1959, 42 (6), 2073–2103. 1.6 MB. http://dx.doi.org/10.1002/hlca.19590420638

Hofmann, A; Heim, R; Brack, A; Kobel, H; Frey, A; Ott, H; Petrzilka, T; Troxler, F. Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen. Helv. Chim. Acta, 1959, 42 (5), 1557–1572. 1.1 MB. http://dx.doi.org/10.1002/hlca.19590420518

Gartz, J. Extraction and analysis of indole derivatives from fungal biomass. J. Basic. Microbiol., 1994, 34 (1), 17–22. 614 kB. http://dx.doi.org/10.1002/jobm.3620340104

Meyers-Riggs, B. 4-Hydroxy tryptamines. countyourculture, countyourculture: rational exploration of the underground, 7 Jul 2012.

Sarwar, M; McDonald, JL. A rapid extraction and GC/MS methodology for the identification of psilocyn in mushroom/chocolate concoctions. Microgram J., 1 Jul 2003, 1 (3–4), 177–183. 211 kB.

Sard, H; Kumaran, G; Morency, C; Roth, BL; Toth, BA; Hec, P; Shuster, L. SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist. Bioorg. Med. Chem. Lett., 1 Jan 2005, 15 (20), 4555–4599. 134 kB. http://dx.doi.org/10.1016/j.bmcl.2005.06.104

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. http://dx.doi.org/10.1016/0028-3908(90)90001-8

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. http://dx.doi.org/10.1016/j.forsciint.2011.11.003

Migliaccio, GP; Shieh, TN; Byrn, SR; Hathaway, BA; Nichols, DE. Comparison of solution conformational preferences for the hallucinogens bufotenin and psilocin using 360-MHz proton NMR spectroscopy. J. Med. Chem., 1 Feb 1981, 24 (2), 206–209. 564 kB. http://dx.doi.org/10.1021/jm00134a016

Morris, H. Blood Spore: Of Murder and Mushrooms. Harper’s Magazine, 1 Jul 2013, 41–56. 13.8 MB.

Rodriguez-Cruz, SE. Analysis and characterization of psilocybin and psilocin using liquid chromatography-electrospray ionization mass spectrometry (LC-ESI-MS) with collision-induced-dissociation (CID) and source-induced-dissociation (SID). Microgram J., 1 Jul 2005, 3 (3–4), 175–182. 560 kB.

Wiseman-Distler, MH; Sourkes, TL. The effect of 4-hydroxyindoles on the metabolism of 5-hydroxytryptamine (serotonin). Ann. N. Y. Acad. Sci., 1 Jan 1962, 96, 142–151. 458 kB. http://dx.doi.org/10.1111/j.1749-6632.1962.tb50109.x

Pellegrini, M; Rotolo, MC; Marchei, E; Pacifici, R; Saggio, F; Pichini, S. Magic truffles or philosopher’s stones: a legal way to sell psilocybin? Drug Test. Analysis, 1 Mar 2013, 5 (3), 182–185. 219 kB. http://dx.doi.org/10.1002/dta.1400

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 1 Oct 2014, 231 (21), 4135-4144. 298 kB. http://dx.doi.org/10.1007/s00213-014-3557-7

Heim, R; Genest, K; Hughes, DW; Belec, G. Botanical and chemical characterisation of a forensic mushroom specimen of the genus psilocybe. J. Forensic Sci. Soc., 1 Jul 1966, 6 (4), 192–201. 2.1 MB. http://dx.doi.org/10.1016/S0015-7368(66)70336-3

McKenna, DJ. Monoamine oxidsase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12.2 MB.

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. http://dx.doi.org/10.1124/mol.107.039255

Shulgin, AT. Drug testing for mushrooms. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 1 Dec 2004.

Shulgin, AT. Psilocybe mushroom extractions. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 5 Mar 2003.

Repke, DB; Ferguson, WJ; Bates, DK. Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols. J. Heterocycl. Chem., 1 Jan 1981, 18 (1), 175–179. 368 kB. http://dx.doi.org/10.1002/jhet.5570180131

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB.

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. http://dx.doi.org/10.1016/j.bmc.2008.02.033

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. http://dx.doi.org/10.1371/journal.pone.0009019

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3), 364–381. 817 kB. http://dx.doi.org/10.1016/j.neuropharm.2011.01.017

Meyers-Riggs, B. Grid biosynthesis of psilocybin. countyourculture, countyourculture: rational exploration of the underground, 5 Dec 2011.

Meyers-Riggs, B. Biosynthesis of 4-substituted tryptamine derivatives. countyourculture, countyourculture: rational exploration of the underground, 17 Feb 2012.

Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. http://dx.doi.org/10.1016/j.pbb.2007.06.001

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. http://dx.doi.org/10.1021/jm00190a014

Gross, ST. Psychotropic drugs in developmental mushrooms: A case study review. J. Forensic Sci., 1 Nov 2002, 47 (6), 1–5. 369 kB. http://dx.doi.org/10.1520/JFS15564J

Gross, ST. Detecting psychoactive drugs in the developmental stages of mushrooms. J. Forensic Sci., 1 May 2000, 45 (3), 527–537. 6.2 MB. http://dx.doi.org/10.1520/JFS14725J

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. http://dx.doi.org/10.1016/0024-3205(91)90582-V

Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3.1 MB. http://dx.doi.org/10.1007/BF02818560

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. http://dx.doi.org/10.1016/0024-3205(68)90200-2

4-HO-DBT
4-HO-DET
4-HO-DIPT
4-HO-DPT
4-HO-MET
4-HO-MIPT
4-HO-MPT
4-HO-DSBT
4-HO-NMT
4-HO-T
4-HO-MBT
4-HO-MIBT
4-HO-MSBT
4-HO-MTBT
4-HO-DTBT
4-HO-DIBT
4-HO-DALT
5535
5536
5-HO-DPT
α-Methylpsilocin
CMY · 1-Methylpsilocin
2-Methylpsilocin
DMT
4-H2PO4-DMT · Psilocybin
4-MeO-DMT
4-MeS-DMT
4-AcO-DMT
4-Amino-DMT
4-F-DMT
5483
5484
4-HO-5-MeO-DMT
5-Formylpsilocin
5-Bromopsilocin
6-Fluoropsilocin
7-Fluoropsilocin
7-Formylpsilocin
7-Bromopsilocin
4-HO-pyr-T
4-HO-pip-T
4-HO-mor-T
4-HO-MPMI
4-HO-dmpip-T
4-HO-phpip-T
5539
4-HO-mepipaz-T
4-HO-thiq-T
5245
4-HO-DMHT
4-HO-N-Me-IPYR
5479
5-MeO-α-MT · α,O-DMS
5-HO-DMT
5-MeO-NMT
6-HO-DMT
7-MeO-NMT
4-MeO-NMT
7-HO-DMT
DMT N-oxide
5246
5248
4-MeO-α-MT
6-MeO-α-MT
5-EtO-T
5-MeO-2-Me-T · 2,O-DMS
4-HO-DBT
4-HO-DET
4-HO-DIPT
4-HO-DPT
4-HO-MET
4-HO-MIPT
4-HO-MPT
4-HO-DSBT
4-HO-NMT
4-HO-T
4-HO-MBT
4-HO-MIBT
4-HO-MSBT
4-HO-MTBT
4-HO-DTBT
4-HO-DIBT
4-HO-DALT
5535
5536
5-HO-DPT
α-Methylpsilocin
CMY · 1-Methylpsilocin
2-Methylpsilocin
DMT
4-H2PO4-DMT · Psilocybin
4-MeO-DMT
4-MeS-DMT
4-AcO-DMT
4-Amino-DMT
4-F-DMT
5483
5484
4-HO-5-MeO-DMT
5-Formylpsilocin
5-Bromopsilocin
6-Fluoropsilocin
7-Fluoropsilocin
7-Formylpsilocin
7-Bromopsilocin
4-HO-pyr-T
4-HO-pip-T
4-HO-mor-T
4-HO-MPMI
4-HO-dmpip-T
4-HO-phpip-T
5539
4-HO-mepipaz-T
4-HO-thiq-T
5245
4-HO-DMHT
4-HO-N-Me-IPYR
5479
5-MeO-α-MT · α,O-DMS
5-HO-DMT
5-MeO-NMT
6-HO-DMT
7-MeO-NMT
4-MeO-NMT
7-HO-DMT
DMT N-oxide
5246
5248
4-MeO-α-MT
6-MeO-α-MT
5-EtO-T
5-MeO-2-Me-T · 2,O-DMS
25 July 2017 · Creative Commons BY-NC-SA ·