Chemistry:Psilocin

From HandWiki

Psilocin, also known as 4-hydroxy-N,N-dimethyltryptamine (4-HO-DMT), is a psychedelic drug and fungal alkaloid of the tryptamine and 4-hydroxytryptamine families.[1][2][3] Along with its phosphate ester psilocybin, it is found in most species of psilocybin-containing mushrooms, such as Psilocybe cubensis and Psilocybe mexicana, and is the compound responsible for their hallucinogenic effects, although concentrations of psilocin are variably lower than those of psilocybin.[4][2][5] The drug is taken orally and its effects include perceptual changes and visual effects, emotional changes, ego dissolution, time dilation, and mystical experiences, among others.[3][6][7] Psilocybin, as well as synthetic acyl esters such as 4-AcO-DMT (psilacetin; O-acetylpsilocin) and 4-PrO-DMT (O-propionylpsilocin), are prodrugs of psilocin and have similar properties and effects.[1][8][3]

Psilocin acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor among others.[9] The drug produces its hallucinogenic effects specifically via activation of the serotonin 5-HT2A receptor.[10][11][12] However, other serotonin receptors, such as the serotonin 5-HT1A and 5-HT2C receptors, may also contribute to its effects.[13][14][15] Notable analogues of psilocin include dimethyltryptamine (DMT), its positional isomer bufotenin (5-HO-DMT), its higher homologue 4-HO-MET (metocin), and others.[3]

Psilocin and psilocybin were discovered via isolation from psilocybin-containing mushrooms by Albert Hofmann in 1958.[1][16][17] This followed the Western re-discovery of psilocybin-containing mushrooms by Robert Gordon Wasson and Valentina Pavlovna Wasson in Mexico in 1955.[16][17] Psilocin, in the form of psilocybin, psilocybin-containing mushrooms, and other prodrugs such as 4-AcO-DMT, is a widely used entheogen as well as recreational psychedelic drug.[16][1][18] Psilocybin and psilocin became controlled substances in the United States and internationally under the United Nations in 1971.[19][20] Since then, psilocin, as the active form of psilocybin, has become of interest for potential use in medicine to treat psychiatric disorders such as depression.[16][18][21] Psilocybin was approved for such purposes in Australia in 2023[22][23] and is in late-stage clinical trials in the United States and other countries.[24][25][26]

Use and effects

Dried psilocybin mushrooms. (Notice the characteristic blue bruising by the stems of the mushrooms.)

Psilocin is used recreationally, spirituality or shamanically, and medically. It is most commonly used in the form of its prodrugs such as psilocybin and 4-AcO-DMT (psilacetin). However, psilocin may also be used itself, either in the form of psilocybin-containing mushrooms (which variably contain psilocin up to similar amounts as psilocybin) or in synthetic form.[3]

Psilocin is usually used orally, but may also be taken intravenously. In terms of dose, it is slightly more potent than psilocybin, about 1.4-fold so (i.e., 1.4 mg psilocybin equals about 1.0 mg psilocin).[4][27][28] This is related to psilocin's lack of ester prodrug moiety, which results in its molecular weight being about 40% lower than that of psilocybin (204 g/mol and 284 g/mol, respectively).[27][29][28] The human dose of psilocin has been given as 10 to 20 mg orally.[10][30][11][3]

In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin described the properties and effects of psilocin, either as psilocin itself, as a prodrug like psilocybin or 4-AcO-DMT, or as Psilocybe cubensis mushrooms.[3] The dose, regardless of form, was listed as 10 to 20 mg orally and the duration as 3 to 6 hours.[3] The onset, in the case of psilocin specifically, was 15 to 40 minutes.[3] The perceptual and related effects included brightened colors, increased visual contrast, closed-eye visuals such as patterns, textures, and colors, open-eye visuals such as colors, distortions, and movement, pareidolia, increased appreciation of scenery, perceiving beauty, and enhanced imagination.[3] Other effects variably included feeling intoxicated, high, and/or stimulated, feelings of peacefulness and serenity, emotional amplification, mood swings, feelings of neuroticism and introversion, feelings of despair, apathy, and unpleasantness, anxiety, confusion, distractibility, impairment, and feeling heavy and tired.[3] Side effects included chills, nausea, vomiting, and motion sickness, but no hangover.[3]

In other reports, the effects observed after ingestion of psilocin can include but are not limited to tachycardia, dilated pupils, restlessness or arousal, euphoria, open and closed eye visuals (common at medium to high doses), synesthesia (e.g. hearing colors and seeing sounds), increased body temperature, headache, sweating and chills, and nausea.[31]

Contraindications

Side effects

There has been no direct lethality associated with psilocin.[32][33] There has been no reported withdrawal syndrome when chronic use of this drug is ceased.[32][34] There is cross tolerance among psilocin, mescaline, lysergic acid diethylamide (LSD), and other psychedelics due to downregulation of these receptors.[1][10][12][14]

Overdose

Interactions

Pharmacology

Pharmacodynamics

Template:Psilocin activities

Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or some species of psychedelic mushrooms. Psilocybin is rapidly dephosphorylated in the body to psilocin which acts as a serotonin 5-HT2A, 5-HT2C and 5-HT1A receptor agonist or partial agonist. Psilocin exhibits functional selectivity in that it activates phospholipase A2 instead of activating phospholipase C as the endogenous ligand serotonin does. Psilocin is structurally similar to serotonin (5-hydroxytryptamine),[32] differing only by the hydroxyl group being on the 4-position rather than the 5 and the dimethyl groups on the nitrogen. Its effects are thought to come from its agonist activity at 5-HT2A receptors in the prefrontal cortex. Psilocin's psychedelic effects are directly correlated with the drug's occupancy at these receptor sites.[35] The drug shows pronounced biased agonism at the serotonin 5-HT2C receptor.[36] Psilocin has no significant effect on dopamine receptors only affects the noradrenergic system at very high doses.[37]

Psilocin has been reported to act as a highly potent positive allosteric modulator of the tropomyosin receptor kinase B (TrkB), one of the receptors of brain-derived neurotrophic factor (BDNF).[38][39][40] However, subsequent studies failed to reproduce these findings and instead found no interaction of psilocin with TrkB.[9]

The cryo-EM structures of the serotonin 5-HT2A receptor with psilocin, as well as with various other psychedelics and serotonin 5-HT2A receptor agonists, have been solved and published by Bryan L. Roth and colleagues.[41][42]

Pharmacokinetics

Psilocin's elimination half-life ranges from 1 to 3 hours depending on route of administration of psilocybin.[4]

Chemistry

Psilocin, also known as 4-hydroxy-N,N-dimethyltryptamine (4-HO-DMT), is a tryptamine derivative.[3] It is closely structurally related to the neurotransmitter serotonin (which is 5-hydroxytryptamine, also known as 5-HT or 5-HO-T), as well as to the naturally occurring psychedelics dimethyltryptamine (N,N-dimethyltryptamine; DMT) and bufotenin (5-hydroxy-N,N-DMT; 5-HO-DMT). Psilocybin is psilocin's O-phosphate ester (4-phosphoryloxy-N,N-DMT; 4-PO-DMT).[3]

Synthesis

The chemical synthesis of psilocin has been described.[3] It can be obtained by dephosphorylation of psilocybin under strongly acidic or under alkaline conditions (hydrolysis). A synthetic route uses the Speeter–Anthony tryptamine synthesis procedure. First, 4-hydroxyindole is Friedel-Crafts-acylated with oxalyl chloride in position 3. The compound is further reacted with dimethylamine, yielding the indole-3-yl-glyoxamide. Finally, this 4-hydroxyindole-3-N,N-dimethylglyoxamide is reduced by lithium aluminum hydride yielding psilocin.[43]

Stability

Psilocin is relatively unstable in solution due to its phenolic hydroxy (-OH) group. In the presence of oxygen, it readily forms bluish and dark black degradation products.[44] Similar products are also formed in the presence of oxygen and Fe3+ ions.{{Citation needed|date=November 2025}

Analogues

Analogues of psilocin (4-HO-DMT) include dimethyltryptamine (DMT), 4-hydroxytryptamine (4-HT or 4-HO-T), norpsilocin (4-HO-NMT), 4-HO-TMT, 4-HO-MET (metocin), 4-HO-DET (ethocin), 4-HO-MPT (meprocin), 4-HO-DPT (deprocin), 4-HO-MiPT (miprocin), 4-HO-DiPT (diprocin), 4-MeO-DMT, and 5-MeO-DMT, among others.[3][45][46][47]

A number of ester prodrugs of psilocin are known, such as psilocybin (4-PO-DMT), 4-AcO-DMT, and 4-PrO-DMT.[1][8][3] Psilocybin is the O-phosphate ester of psilocin, while 4-AcO-DMT is the O-acetyl ester and 4-PrO-DMT is the O-propionyl ester.[1][8][3] Another ester is 4-GO-DMT (4-HO-DMT O-glutarate; RE109), which is related to luvesilocin (4-GO-DiPT; RE104).[48][49] Analogues of psilocin prodrugs include norbaeocystin (4-PO-T), baeocystin (4-PO-NMT), aeruginascin (4-PO-TMT), and ethocybin (4-PO-DET), among others.[3][2][50]

Bufotenin (5-HO-DMT), 6-HO-DMT, and 7-HO-DMT are positional isomers of psilocin.[51][45][46][47]

1-Methylpsilocin is a serotonin 5-HT2C receptor-preferring agonist.[52] 4-Fluoro-DMT[52] and 4-methyl-DMT are known.[53][54] Another analogue of psilocin is 1-isopropyl-6-fluoropsilocin (O-4310).[55][56]

Sulfur analogues of psilocin are known with a benzothienyl replacement[57] as well as 4-SH-DMT.[58]

History

Psilocin and its phosphorylated cousin, psilocybin, were first isolated and named in 1958 by Swiss chemist Albert Hofmann.[1][16] He obtained the chemicals from laboratory-grown specimens of the hallucinogenic mushroom Psilocybe mexicana.[1][16] Hofmann also succeeded in finding synthetic routes to these chemicals.[59]

Society and culture

United Nations

Psilocin is a Schedule I drug under the Convention on Psychotropic Substances.[60] The United Nations Convention on Psychotropic Substances (adopted in 1971) requires its members to prohibit psilocybin, and parties to the treaty are required to restrict the use of the drug to medical and scientific research under strictly controlled conditions.

Australia

Psilocin is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[61] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[61]

Canada

Psilocin is a Schedule III controlled substance in Canada.[62]

Russia

Psilocin and psilocybin are banned in Russia, due to their status as narcotic drugs, with a criminal penalty for possession of more than 50 mg.[63]

United States

Psilocin is a Schedule I controlled substance in the United States since 1971.[19]

Research

Psilocin is being evaluated under the developmental code name PLZ-1015 for the treatment of pervasive developmental disorders like autism in children.[26] Its prodrug psilocybin is also being studied for treatment of depression and a variety of other conditions.[21][25]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 "DARK Classics in Chemical Neuroscience: Psilocybin". ACS Chem Neurosci 9 (10): 2438–2447. October 2018. doi:10.1021/acschemneuro.8b00186. PMID 29956917. https://shaunlacob.com/wp-content/uploads/2020/12/DC-PSILO.pdf. 
  2. ↑ 2.0 2.1 2.2 "A journey with psychedelic mushrooms: From historical relevance to biology, cultivation, medicinal uses, biotechnology, and beyond". Biotechnol Adv 69. December 2023. doi:10.1016/j.biotechadv.2023.108247. PMID 37659744. 
  3. ↑ 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 3.10 3.11 3.12 3.13 3.14 3.15 3.16 3.17 3.18 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml.  https://www.erowid.org/library/books_online/tihkal/tihkal18.shtml
  4. ↑ 4.0 4.1 4.2 "Psilocybin - summary of knowledge and new perspectives". Eur Neuropsychopharmacol 24 (3): 342–356. March 2014. doi:10.1016/j.euroneuro.2013.12.006. PMID 24444771. https://www.researchgate.net/publication/259517753. 
  5. ↑ "Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids". International Journal of Molecular Sciences 23 (22). November 2022. doi:10.3390/ijms232214068. PMID 36430546. 
  6. ↑ "Opinion Mining of Erowid's Experience Reports on LSD and Psilocybin-Containing Mushrooms". Drug Saf 48 (5): 559–575. May 2025. doi:10.1007/s40264-025-01530-z. PMID 40032797. 
  7. ↑ "Psilocybin occasioned mystical-type experiences". Hum Psychopharmacol 35 (5). September 2020. doi:10.1002/hup.2742. PMID 32573835. 
  8. ↑ 8.0 8.1 8.2 "Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice". ACS Pharmacol Transl Sci 6 (4): 567–577. April 2023. doi:10.1021/acsptsci.2c00222. PMID 37082754. 
  9. ↑ 9.0 9.1 "The polypharmacology of psychedelics reveals multiple targets for potential therapeutics". Neuron 113 (19): 3129–3142.e9. July 2025. doi:10.1016/j.neuron.2025.06.012. PMID 40683247. https://www.cell.com/cms/10.1016/j.neuron.2025.06.012/attachment/7d8365fe-51f3-4a28-bf40-9999bec837f6/mmc11.pdf. "Recent studies have suggested that psychedelics such as LSD directly interact with TrkB with high affinity, promoting BDNF-mediated neuroplasticity and antidepressant-like effects via allosteric potentiation of BDNF signaling in active synapses.8 To investigate this, we screened LSD across 450 human kinases, including TrkB, but found no significant interactions between LSD and any tested human kinases. Further experiments in transfected cells revealed no effect of LSD or psilocin on BDNF-mediated activation of a TrkB reporter. We note that similar negative preliminary results, which have not yet been published in a peer-reviewed journal, were recently reported by Boltaev et al.63". 
  10. ↑ 10.0 10.1 10.2 "Hallucinogens". Pharmacol Ther 101 (2): 131–181. February 2004. doi:10.1016/j.pharmthera.2003.11.002. PMID 14761703. 
  11. ↑ 11.0 11.1 "Psychedelics". Pharmacol Rev 68 (2): 264–355. April 2016. doi:10.1124/pr.115.011478. PMID 26841800. 
  12. ↑ 12.0 12.1 "Recent advances in the neuropsychopharmacology of serotonergic hallucinogens". Behav Brain Res 277: 99–120. January 2015. doi:10.1016/j.bbr.2014.07.016. PMID 25036425. 
  13. ↑ "Beyond the 5-HT2A Receptor: Classic and Nonclassic Targets in Psychedelic Drug Action". J Neurosci 43 (45): 7472–7482. November 2023. doi:10.1523/JNEUROSCI.1384-23.2023. PMID 37940583. 
  14. ↑ 14.0 14.1 "Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens". Neuropharmacology 61 (3): 364–381. September 2011. doi:10.1016/j.neuropharm.2011.01.017. PMID 21256140. 
  15. ↑ "Serotonin 5-HT2A, 5-HT2c and 5-HT1A receptor involvement in the acute effects of psilocybin in mice. In vitro pharmacological profile and modulation of thermoregulation and head-twich response". Biomed Pharmacother 154. October 2022. doi:10.1016/j.biopha.2022.113612. PMID 36049313. 
  16. ↑ 16.0 16.1 16.2 16.3 16.4 16.5 "Psilocybin: from ancient magic to modern medicine". J Antibiot (Tokyo) 73 (10): 679–686. October 2020. doi:10.1038/s41429-020-0311-8. PMID 32398764. 
  17. ↑ 17.0 17.1 "Psilocybin and hallucinogenic mushrooms". CNS Spectr 29 (6): 611–632. December 2024. doi:10.1017/S1092852924002487. PMID 39789676. 
  18. ↑ 18.0 18.1 "The revival of psilocybin between scientific excitement, evidence of efficacy, and real-world challenges". CNS Spectr 29 (6): 570–584. December 2024. doi:10.1017/S1092852924002268. PMID 39655426. 
  19. ↑ 19.0 19.1 "PUBLIC LAW 91-513-OCT. 27, 1970". October 27, 1970. https://www.govinfo.gov/content/pkg/STATUTE-84/pdf/STATUTE-84-Pg1236.pdf. 
  20. ↑ CONVENTION ON PSYCHOTROPIC SUBSTANCES (Report). 1971. https://www.incb.org/documents/Psychotropics/conventions/convention_1971_en.pdf. 
  21. ↑ 21.0 21.1 "Psilocybin for clinical indications: A scoping review". J Psychopharmacol 38 (10): 839–845. October 2024. doi:10.1177/02698811241269751. PMID 39135496. 
  22. ↑ "The Australia story: Current status and future challenges for the clinical applications of psychedelics". British Journal of Pharmacology. December 2024. doi:10.1111/bph.17398. PMID 39701143. 
  23. ↑ "From prohibited to prescribed: The rescheduling of MDMA and psilocybin in Australia". Drug Science, Policy and Law 9. 2023. doi:10.1177/20503245231198472. ISSN 2050-3245. 
  24. ↑ "Uncovering Psychedelics: From Neural Circuits to Therapeutic Applications". Pharmaceuticals (Basel) 18 (1): 130. January 2025. doi:10.3390/ph18010130. PMID 39861191. 
  25. ↑ 25.0 25.1 "The role of psilocybin in depressive disorders". Curr Med Res Opin 40 (10): 1793–1808. October 2024. doi:10.1080/03007995.2024.2396536. PMID 39177339. 
  26. ↑ 26.0 26.1 "Psilocybin - COMPASS Pathways". 15 May 2024. https://adisinsight.springer.com/drugs/800050861. 
  27. ↑ 27.0 27.1 Albert Hofmann (1968). "Psychotomimetic Agents". Drugs Affecting the Central Nervous System. 2. New York: M. Dekker. pp. 169–235. OCLC 245452885. https://archive.org/details/drugsaffectingce0000edit/page/169/mode/1up. "Psilocin is approximately 1.4 times as potent as psilocybin. This ratio is the same as that of the molecular weights of the two drugs." 
  28. ↑ 28.0 28.1 "Comparison of psilocin with psilocybin, mescaline and LSD-25". Psychopharmacologia 3 (3): 219–223. 1962. doi:10.1007/BF00412109. PMID 14007905. "Psilocin is approximately 1.4 times as potent as psilocybin. This ratio is the same as that of the molecular weights of the two drugs.". 
  29. ↑ "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. 1975. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. https://bitnest.netfirms.com/external/Books/978-0-85608-011-1. "Psilocin is claimed to be about 1·4 times as potent as psilocybin, but they are equipotent on a molar basis." 
  30. ↑ "The behavioral pharmacology of hallucinogens". Biochem Pharmacol 75 (1): 17–33. January 2008. doi:10.1016/j.bcp.2007.07.018. PMID 17977517. PMC 2247373. https://www.iceers.org/Documents_ICEERS_site/Scientific_Papers/ayahuasca/Fantegrossi%20et%20al_2008_Behavioral_Pharm_Hallucinogens.pdf. 
  31. ↑ "The Therapeutic Potential of Psilocybin". Molecules 26 (10): 2948. May 2021. doi:10.3390/molecules26102948. PMID 34063505. 
  32. ↑ 32.0 32.1 32.2 How Drugs Influence Behavior: A Neurobehavioral Approach. Englewood Cliffs: Prentice Hall. 1996. ISBN 978-0-02-328764-0. 
  33. ↑ "Clinical applications of hallucinogens: A review". Experimental and Clinical Psychopharmacology 24 (4): 229–68. August 2016. doi:10.1037/pha0000084. PMID 27454674. 
  34. ↑ "Assessing Drug Risks: A Scientific Framework". European Monitoring Centre for Drugs and Drug Addiction. Luxembourg: EMCDDA. 2016. 
  35. ↑ "Psychedelic effects of psilocybin correlate with serotonin 2A receptor occupancy and plasma psilocin levels". Neuropsychopharmacology 44 (7): 1328–1334. June 2019. doi:10.1038/s41386-019-0324-9. PMID 30685771. 
  36. ↑ "Serotonin 5-HT2C Receptor Signaling Analysis Reveals Psychedelic Biased Agonism". ACS Chem Neurosci 16 (19): 3899–3914. October 2025. doi:10.1021/acschemneuro.5c00647. PMID 40944639. 
  37. ↑ "Psilocybin Investigator's Brochure". March–April 2007. https://www.maps.org/research-archive/psilo/psilo_ib.pdf. 
  38. ↑ "The Effects of Psychedelics on Neuronal Physiology". Annu Rev Physiol 86: 27–47. February 2024. doi:10.1146/annurev-physiol-042022-020923. PMID 37931171. 
  39. ↑ "Psilocybin and hallucinogenic mushrooms". CNS Spectr 29 (6): 611–632. January 2025. doi:10.1017/S1092852924002487. PMID 39789676. 
  40. ↑ "Psychedelics promote plasticity by directly binding to BDNF receptor TrkB". Nat Neurosci 26 (6): 1032–1041. June 2023. doi:10.1038/s41593-023-01316-5. PMID 37280397. 
  41. ↑ "The structural diversity of psychedelic drug actions revealed". Nature Communications 16 (1). March 2025. doi:10.1038/s41467-025-57956-7. PMID 40108183. Bibcode: 2025NatCo..16.2734G. 
  42. ↑ "Structures of Hallucinogenic and Non-Hallucinogenic Analogues of the 5-HT2A Receptor Reveals Molecular Insights into Signaling Bias". University of North Carolina at Chapel Hill Department of Pharmacology Research Retreat September 16th, 2022 – William and Ida Friday Center. September 2022. https://www.med.unc.edu/pharm/wp-content/uploads/sites/930/2022/07/COMPLETE-PHARM-RETREAT-PROGRAM-2022-UPDATE.pdf#page=37. 
  43. ↑ "Direct Phosphorylation of Psilocin Enables Optimized cGMP Kilogram-Scale Manufacture of Psilocybin". ACS Omega 5 (27): 16959–16966. July 2020. doi:10.1021/acsomega.0c02387. PMID 32685866. 
  44. ↑ "Injury-Triggered Blueing Reactions of Psilocybe "Magic" Mushrooms". Angewandte Chemie 59 (4): 1450–1454. January 2020. doi:10.1002/anie.201910175. PMID 31725937. Bibcode: 2020ACIE...59.1450L. 
  45. ↑ 45.0 45.1 "Chemistry/structural biology of psychedelic drugs and their receptor(s)". Br J Pharmacol. October 2024. doi:10.1111/bph.17361. PMID 39354889. 
  46. ↑ 46.0 46.1 "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". Hallucinogens: An Update. National Institute on Drug Abuse Research Monograph Series. 146. National Institute on Drug Abuse. 1994. pp. 74–91. https://bibliography.maps.org/resources/download/11534. 
  47. ↑ 47.0 47.1 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://bibliography.maps.org/resources/download/12634. 
  48. ↑ "RE104: Synthesis and Activity of a Novel Serotonergic Psychedelic Prodrug of 4-Hydroxy-N,N-diisopropyltryptamine". ACS Chem Neurosci 15 (12): 2386–2395. June 2024. doi:10.1021/acschemneuro.4c00058. PMID 38758589. 
  49. ↑ "Improved pharmacokinetics of tryptamine prodrugs". 4 January 2024. https://patents.google.com/patent/WO2024145719A1/. 
  50. ↑ "Structure-Activity Relationships for Psilocybin, Baeocystin, Aeruginascin, and Related Analogues to Produce Pharmacological Effects in Mice". ACS Pharmacol Transl Sci 5 (11): 1181–1196. November 2022. doi:10.1021/acsptsci.2c00177. PMID 36407948. 
  51. ↑ "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neurosci Biobehav Rev 6 (4): 489–497. 1982. doi:10.1016/0149-7634(82)90030-6. PMID 6757811. 
  52. ↑ 52.0 52.1 "SAR of psilocybin analogs: discovery of a selective 5-HT 2C agonist". Bioorganic & Medicinal Chemistry Letters 15 (20): 4555–4559. October 2005. doi:10.1016/j.bmcl.2005.06.104. PMID 16061378. 
  53. ↑ "Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines". J Med Chem 27 (1): 41–45. January 1984. doi:10.1021/jm00367a008. PMID 6581313. "[...] the affinity of isoDMT (7a) was compared with that of DMT (1; pA2 = 6.006). [...] (8) A PA2 value has not been previously reported for 4,N,N-trimethyltryptamine (4-Me-DMT) but was determined, during the course of this study, to be 6.85 (±0.26); Schild slope = 0.93 (±0.21), n = 4. [...] Experimental Section [...] 4,N,N-Trimethyltryptamine Hydrogen Oxalate. [...]". 
  54. ↑ "DOM-stimulus generalization to LSD and other hallucinogenic indolealkylamines". Eur J Pharmacol 86 (3-4): 453–459. January 1983. doi:10.1016/0014-2999(83)90196-6. PMID 6572591. 
  55. ↑ "The effect of maternal forced exercise on offspring pain perception, motor activity and anxiety disorder: the role of 5-HT2 and D2 receptors and CREB gene expression". Journal of Exercise Rehabilitation 13 (5): 514–525. October 2017. doi:10.12965/jer.1734992.496. PMID 29114525. 
  56. ↑ Kumaran G, Morency C, Roth B, Sard HP, Shuster L Xu L, "Indole compounds useful as serotonin selective agents.", US patent 7655691, published 11 May 2006, assigned to Organix Incand Tufts University, Case Western Reserve University
  57. ↑ "Synthesis of the sulphur analogue of psilocin and some related compounds". Journal of the Chemical Society, Perkin Transactions 1: 3011–15. 1972. doi:10.1039/P19720003011. http://pubs.rsc.org/en/Content/ArticleLanding/1972/P1/p19720003011. 
  58. ↑ Hofmann A, Troxler F, CH patent 421960, issued 1967; CA 68:95680n
  59. ↑ "Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen" (in de). Helvetica Chimica Acta 42 (5): 1557–72. 1959. doi:10.1002/hlca.19590420518. Bibcode: 1959HChAc..42.1557H. 
  60. ↑ "List of psychotropic substances under international control". Vienna Austria: International Narcotics Control Board. August 2003. http://www.incb.org/pdf/e/list/green.pdf. 
  61. ↑ 61.0 61.1 "Poisons Standard". Therapeutics Goods Administration, Department of Health. Australian Government. October 2015. https://www.comlaw.gov.au/Details/F2015L01534. 
  62. ↑ "Controlled Drugs and Substances Act". 5 December 2025. https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  63. ↑ "On approval of significant, large and particularly large amounts of narcotic drugs and psychotropic substances, as well as significant, large and particularly large sizes for plants containing narcotic drugs or psychotropic substances, or parts thereof, containing narcotic drugs or psychotropic substances for the purposes of articles 228, 228.1, 229 and 229.1 of the Criminal Code of the Russian Federation (as amended) (translated)". Resolution of the Government of the Turkish Federation. Criminal Code of the Russian Federation. 1 October 2012. http://base.garant.ru/70237124/. 



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