Psilocin information

Psilocin
Clinical data
Other names	4-hydroxy-N,N-dimethyltryptamine
Routes of; administration	Oral, IV
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule III; DE: Anlage I (Authorized scientific use only); NZ: Class A; UK: Class A; US: Schedule I; UN: Psychotropic Schedule I;
Pharmacokinetic data
Metabolism	Hepatic
Elimination half-life	1-3 hours
Excretion	Urine
Identifiers
	IUPAC name 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol;
CAS Number	520-53-6 ;
PubChem CID	4980;
IUPHAR/BPS	11291;
ChemSpider	4807 ;
UNII	CMS88KUW0G;
KEGG	C08312 ;
ChEBI	CHEBI:8613 ;
ChEMBL	ChEMBL65547 ;
CompTox Dashboard (EPA)	DTXSID5048899 ;
ECHA InfoCard	100.007.543
Chemical and physical data
Formula	C12H16N2O
Molar mass	204.273 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	173 to 176 °C (343 to 349 °F)
	SMILES CN(C)CCc1c[nH]c2cccc(O)c12;
	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 ; Key:SPCIYGNTAMCTRO-UHFFFAOYSA-N ;
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Psilocin (also known as 4-HO-DMT, 4-hydroxy DMT, psilocine, psilocyn, or psilotsin) is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms^[3] together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances.^[4] Acting on the 5-HT_2A receptors, psilocin modulates the production and reuptake of serotonin.^[5] The mind-altering effects of psilocin are highly variable and subjective and resemble those of LSD and DMT.

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ Tylš F, Páleníček T, Horáček J (March 2014). "Psilocybin--summary of knowledge and new perspectives". European Neuropsychopharmacology. 24 (3): 342–356. doi:10.1016/j.euroneuro.2013.12.006. PMID 24444771. S2CID 10758314.
^ Gotvaldová K, Borovička J, Hájková K, Cihlářová P, Rockefeller A, Kuchař M (November 2022). "Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids". International Journal of Molecular Sciences. 23 (22): 14068. doi:10.3390/ijms232214068. PMC 9693126. PMID 36430546.
^ "List of psychotropic substances under international control" (PDF) (23rd ed.). Vienna Austria: International Narcotics Control Board. August 2003. Archived from the original (PDF) on 4 February 2012. Retrieved 2012-10-11.
^ Madsen MK, Fisher PM, Burmester D, Dyssegaard A, Stenbæk DS, Kristiansen S, et al. (June 2019). "Psychedelic effects of psilocybin correlate with serotonin 2A receptor occupancy and plasma psilocin levels". Neuropsychopharmacology. 44 (7): 1328–1334. doi:10.1038/s41386-019-0324-9. PMC 6785028. PMID 30685771.

[1] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[rev-2] Tylš F, Páleníček T, Horáček J (March 2014). "Psilocybin--summary of knowledge and new perspectives". European Neuropsychopharmacology. 24 (3): 342–356. doi:10.1016/j.euroneuro.2013.12.006. PMID 24444771. S2CID 10758314.

[3] Gotvaldová K, Borovička J, Hájková K, Cihlářová P, Rockefeller A, Kuchař M (November 2022). "Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids". International Journal of Molecular Sciences. 23 (22): 14068. doi:10.3390/ijms232214068. PMC 9693126. PMID 36430546.

[4] "List of psychotropic substances under international control" (PDF) (23rd ed.). Vienna Austria: International Narcotics Control Board. August 2003. Archived from the original (PDF) on 4 February 2012. Retrieved 2012-10-11.

[5] Madsen MK, Fisher PM, Burmester D, Dyssegaard A, Stenbæk DS, Kristiansen S, et al. (June 2019). "Psychedelic effects of psilocybin correlate with serotonin 2A receptor occupancy and plasma psilocin levels". Neuropsychopharmacology. 44 (7): 1328–1334. doi:10.1038/s41386-019-0324-9. PMC 6785028. PMID 30685771.

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Clinical data


Other names	4-hydroxy-N,N-dimethyltryptamine
Routes of administration	Oral, IV
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics)^[1] CA: Schedule III DE: Anlage I (Authorized scientific use only) NZ: Class A UK: Class A US: Schedule I UN: Psychotropic Schedule I
Pharmacokinetic data
Metabolism	Hepatic
Elimination half-life	1-3 hours^[2]
Excretion	Urine
Identifiers
IUPAC name 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
CAS Number	520-53-6^Y
PubChem CID	4980
IUPHAR/BPS	11291
ChemSpider	4807^Y
UNII	CMS88KUW0G
KEGG	C08312^Y
ChEBI	CHEBI:8613^Y
ChEMBL	ChEMBL65547^Y
CompTox Dashboard (EPA)	DTXSID5048899
ECHA InfoCard	100.007.543
Chemical and physical data
Formula	C₁₂H₁₆N₂O
Molar mass	204.273 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	173 to 176 °C (343 to 349 °F)
SMILES CN(C)CCc1c[nH]c2cccc(O)c12
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^Y Key:SPCIYGNTAMCTRO-UHFFFAOYSA-N^Y
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