Exploring Psilocybin. To explore a different substance…

Names:
4-H2PO4-DMT · PSOP · CY-39 · 4-HO-DMT phosphate ester · Psilocybin · Psilocin, phosphate ester · Tryptamine, N,N-dimethyl-4-phosphoryloxy · 3-[2-(Dimethylamino)ethyl]-4-indolol, phosphate ester · 4-Indolol, 3-[2-(dimethylamino)ethyl], phosphate ester · N,N-Dimethyl-4-phosphoryloxytryptamine
IUPAC name:
3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate
ID: 5058 · Formula: C12H17N2O4P · Molecular weight: 284.248
InChI: InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)

Wark, C. A social and cultural history of the federal prohibition of psilocybin. Ph. D. Thesis, University of Missouri-Columbia, Columbia, MO, 1 Aug 2007. 2.2 MB.

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

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

Nichols, DE. Commentary on: “Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance” by Griffiths et al. Psychopharmacology, 1 Aug 2006, 187 (3), 284–286. 71 kB. http://dx.doi.org/10.1007/s00213-006-0458-4

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

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

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

Griffiths, RR; Richards, WA; McCann, U; Jesse, R. Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance. Psychopharmacology, 1 Aug 2006, 187 (3), 268–283. 342 kB. http://dx.doi.org/10.1007/s00213-006-0457-5

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

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

Gouzoulis-Mayfrank, E. Differential actions of an entactogen compared to a stimulant and a hallucinogen in healthy humans. In Heffter Review; Nichols, DE, Ed., Heffter Research Institute, Santa Fe, NM, 2001; Vol. 2, pp 64–72. 261 kB.

Passie, T; Seifert, J; Schneider, U; Emrich, HM. The pharmacology of psilocybin. Addict. Biol., 1 Jan 2002, 7 (4), 357–364. 184 kB. http://dx.doi.org/10.1080/1355621021000005937

McKenna, DJ. Monoamine odixase 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.

Bunch, KS. Psilocybin and spiritual experience. Psy. D. Thesis, Alliant International University, San Francisco, CA, USA, 1 Aug 2009. 5.7 MB.

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

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

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

Leung, AY; Paul, AG. Baeocystin and norbaeocystin: New analogs of psilocybin from Psilocybe baeocystis. J. Pharm. Sci., 1 Jan 1968, 57 (10), 1667–1671. 399 kB. http://dx.doi.org/10.1002/jps.2600571007

Nichols, DE; Frescas, SP. Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin. Synthesis, 1 Jan 1999, 1999, 935–938. 1.5 MB. http://dx.doi.org/10.1055/s-1999-3490

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. http://dx.doi.org/10.1002/cmdc.200800133

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.

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

Vollenweider, FX; Kometer, M. The neurobiology of psychedelic drugs: implications for the treatment of mood disorders. Nat. Rev. Neurosci., 1 Sep 2010, 11 (9), 642–651. 588 kB. http://dx.doi.org/10.1038/nrn2884

Agurell, S; Nilsson, JLG. Biosynthesis of psilocybin. Part II. Incorporation of labelled tryptamine derivatives. Acta Chem. Scand., 1 Jan 1968, 22 (4), 1210–1218. 805 kB. http://dx.doi.org/10.3891/acta.chem.scand.22-1210

Shulgin, AT. Profiles of psychedelic drugs. 8. Psilocybin. J. Psychedelic Drugs, 1 Jan 1980, 12 (1), 79. 1.6 MB. http://dx.doi.org/10.1080/02791072.1980.10471557

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

4-HO-DET phosphate ester · Ethocybin
Baeocystin
Norbaeocystin
Aeruginascin
1-Methylpsilocybin
1-Butylpsilocybin
DMT
4-HO-DMT · Psilocin
4-MeO-DMT
4-MeS-DMT
4-AcO-DMT
4-Amino-DMT
4-F-DMT
5483
5484
4-HO-DET phosphate ester · Ethocybin
Baeocystin
Norbaeocystin
Aeruginascin
1-Methylpsilocybin
1-Butylpsilocybin
DMT
4-HO-DMT · Psilocin
4-MeO-DMT
4-MeS-DMT
4-AcO-DMT
4-Amino-DMT
4-F-DMT
5483
5484
23 February 2017 · Creative Commons BY-NC-SA ·