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
5058 · C12H17N2O4P · 284.248
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)
QVDSEJDULKLHCG-UHFFFAOYSA-N This stereoisomer Any stereoisomer

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. https://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. https://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. https://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. https://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.

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

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. https://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. https://doi.org/10.3891/acta.chem.scand.22-1210

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

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

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

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

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.

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

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. https://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. https://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. https://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. https://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. https://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. https://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. https://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. https://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. https://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.

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.

Fricke, J; Blei, F; Hoffmeister, D. Enzymatic synthesis of psilocybin. Angew. Chem. Int. Ed., 20 Aug 2017, 56 (40), 12352-12355. 1.8 MB. https://doi.org/10.1002/anie.201705489

Brandt, SD; Martins, CP. Analytical methods for psychoactive N,N-dialkylated tryptamines. Trends Anal. Chem., 1 Sep 2010, 29 (8), 858–869. 446 kB. https://doi.org/10.1016/j.trac.2010.04.008 #16

Swanson, LR. Unifying theories of psychedelic drug effects. Front. Pharmacol., 2 Mar 2018, 9 n/a. 1.7 MB. https://doi.org/10.3389/fphar.2018.00172

Baker, LE. Hallucinogens in drug discrimination. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 201-219. 342 kB. https://doi.org/10.1007/7854_2017_476

Anastos, N; Barnett, N; Lewis, S; Gathergood, N; Scammells, P; Sims, D. Determination of psilocin and psilocybin using flow injection analysis with acidic potassium permanganate and tris(2,2′-bipyridyl)ruthenium(II) chemiluminescence detection respectively. Talanta, 15 Aug 2005, 67 (2), 354-359. 111 kB. https://doi.org/10.1016/j.talanta.2004.11.038

Clarke, EGC. The identification of some proscribed psychedelic drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 46-50. 336 kB. https://doi.org/10.1016/S0015-7368(67)70370-9

Hermle, L; Kraehenmann, R. Experimental psychosis research and schizophrenia—Similarities and dissimilarities in psychopathology. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 313-332. 446 kB. https://doi.org/10.1007/7854_2016_460

Marek, GJ. Interactions of hallucinogens with the glutamatergic system: Permissive network effects mediated through cortical layer V pyramidal neurons. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 107-135. 1.2 MB. https://doi.org/10.1007/7854_2017_480

Halberstadt, AL; Geyer, MA. Effect of hallucinogens on unconditioned behavior. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 159-199. 652 kB. https://doi.org/10.1007/7854_2016_466

Halpern, JH; Lerner, AG; Passie, T. A review of hallucinogen persisting perception disorder (HPPD) and an exploratory study of subjects claiming symptoms of HPPD. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 333-360. 579 kB. https://doi.org/10.1007/7854_2016_457

Barrett, FS; Griffiths, RR. Classic hallucinogens and mystical experiences: Phenomenology and neural correlates. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 137-158. 848 kB. https://doi.org/10.1007/7854_2017_474

Bogenschutz, MP; Ross, S. Therapeutic applications of classic hallucinogens. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 361-391. 360 kB. https://doi.org/10.1007/7854_2016_464

Nichols, DE. Psychedelics. Pharmacol. Rev., 1 Apr 2016, 68 (2), 264-355. 1.9 MB. https://doi.org/10.1124/pr.115.011478 Updated with published correction to Figure 4 (the α-methyl group was missing in the original)

McKenna, D; Riba, J. New world tryptamine hallucinogens and the neuroscience of ayahuasca. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2016; pp 283-311. 749 kB. https://doi.org/10.1007/7854_2016_472

Helm, K. Synthese und funktionelle In-vitro-Pharmakologie neuer Liganden des 5-HT2A-Rezeptors aus der Klasse. Ph. D. Thesis, Universität Regensburg, Dresden, 1 Jan 2014. 3.2 MB. #29

Beug, MW; Bigwood, J. Quantitative analysis of psilocybin and psilocin and Psilocybe baecystis (Singer and Smith) by high-performance liquid chromatography and by thin-layer chromatography. J. Chromatogr. A, 27 Mar 1981, 207 (3), 379-385. 514 kB. https://doi.org/10.1016/S0021-9673(00)88741-5 #I

Tylš, F; Páleníček, T; Horáček, J. Psilocybin – Summary of knowledge and new perspectives. Eur. Neuropsychopharmacol., 1 Mar 2014, 24 (3), 342–356. 710 kB. https://doi.org/10.1016/j.euroneuro.2013.12.006

Shulgin, AT. Basic Pharmacology and Effects. In Hallucinogens. A Forensic Drug Handbook; Laing, R; Siegel, JA, Eds., Academic Press, London, 2003; pp 67–137. 6.3 MB.

Jacob, P; Shulgin, AT. Structure-activity relationships of the classic hallucinogens and their analogs. In Hallucinogens: An update. NIDA Research Monograph 146; Lin, GC; Glennon, RA, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1994; pp 74–91. 51 kB.

Shulgin, AT. Chemistry of psychotomimetics. In Handbook of Experimental Pharmacology. Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs; Hoffmeister, F; Stille, G, Eds., Springer-Verlag, Berlin, 1982; Vol. 55 (3), pp 3–29. 29.7 MB. #4g

Shulgin, AT. Hallucinogens. In Burger’s Medicinal Chemistry, 4th ed., Part III; Wolff, ME, Ed., Wiley & Co., 1981; pp 1109–1137. 4.7 MB. #29f

Nicholas, CR; Henriquez, KM; Gassman, MC; Cooper, KM; Muller, D; Hetzel, S; Brown, RT; Cozzi, NV; Thomas, C; Hutson, PR. High dose psilocybin is associated with positive subjective effects in healthy volunteers. J. Psychopharmacol., 27 Jun 2018, n/a. 1.3 MB. https://doi.org/10.1177/0269881118780713 #Psilocybin

Shulgin, AT. Psychotomimetic agents. In Psychopharmacological Agents; Gordon, M, Ed., Academic Press, New York, 1976; Vol. 4, pp 59–146. 3.1 MB. #XXIX

Hoffer, A; Osmond, H. The Hallucinogens, Academic Press, New York, 1967. 3.9 MB. #Psilocybin

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