5-MeO-DMT

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5-MeO-DMT
5-MeO-DMT.svg
5-MeO-DMT-3d-sticks.png
Systematic (IUPAC) name
2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-2-amine
Clinical data
Routes of
administration
Smoked, Insufflated, Oral
Legal status
Legal status
Identifiers
CAS Number 1019-45-0 N
PubChem CID 1832
IUPHAR/BPS 145
ChemSpider 1766 YesY
UNII X0MKX3GWU9 N
KEGG C08309 YesY
ChEBI CHEBI:2086 YesY
ChEMBL CHEMBL7257 YesY
Chemical data
Formula C13H18N2O
Molar mass 218.298 g/mol
 NYesY (what is this?)  (verify)

5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine) is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and a single psychoactive toad species, the Colorado River toad. Like its close relatives DMT and bufotenin (5-HO-DMT), it has been used as an entheogen in South America.[1]

Chemistry[edit]

5-MeO-DMT was first synthesized in 1936, and in 1959 it was isolated as one of the psychoactive ingredients of Anadenanthera peregrina seeds used in preparing Yopo snuff. It was once believed to be a major component of the psychoactive effects of the snuff, although this has recently been shown to be unlikely, due to the limited or sometimes even non-existent quantity contained within the seeds, which instead achieve their psychoactivity from the O-demethylated metabolite of 5-MeO-DMT, bufotenin.[2][3] It is metabolized mainly by CYP2D6.[3]

Religious use[edit]

5-MeO-DMT is a sacrament of the Church of the Tree of Life. From approximately 1971 to the late 1980s, 5-MeO-DMT was discreetly available to its members.[4] Between 1970 and 1990 smoking of 5-MeO-DMT on parsley was probably one of the two most common forms of ingestion in the United States.[4]

Pharmacology[edit]

5-MeO-DMT is a methoxylated derivative of DMT. Its pharmacological action is mainly through serotonin receptors. Specifically, it shows high affinity for the 5-HT2 and 5-HT1A subtypes.[5] Additional mechanisms of action such as inhibition of monoamine reuptake may be involved also.[6]

Legality[edit]

China[edit]

As of October 2015 5-MeO-DMT is a controlled substance in China.[7]

Australia[edit]

As an analogue of N,N-Dimethyltryptamine, 5-MeO-DMT is a Schedule 9 prohibited substance under the Poisons Standard.[8]

Sweden[edit]

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 5-MeO-DMT, listed as 5-metoxi-N,N-dimetyltryptamin (5-MeO-DMT) in their regulation SFS 2004:696, as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) in October 2004, making it illegal to sell or possess.[9]

Turkey[edit]

5-MeO-DMT is controlled in Turkey since December 2013.[10]

USA[edit]

5-MeO-DMT was made a Schedule I controlled substance in January 2011.[11]

See also[edit]

References[edit]

  1. ^ Araújo, AnaMargarida; Carvalho, Félix; Bastos, Maria deLourdes; Guedes de Pinho, Paula; Carvalho, Márcia (August 2015). "The hallucinogenic world of tryptamines: an updated review". Archives of Toxicology. 89 (8): 1151–1173. doi:10.1007/s00204-015-1513-x. ISSN 0340-5761. PMID 25877327. 
  2. ^ Ott, Jonathan (July–September 2001). "Pharmañopo—Psychonautics: Human Intranasal, Sublingual, Intrarectal, Pulmonary and Oral Pharmacology of Bufotenine". Journal of Psychoactive Drugs. 33 (3): 273–281. doi:10.1080/02791072.2001.10400574. ISSN 0279-1072. PMID 11718320. 
  3. ^ a b Shen, Hong-Wu; Jiang, Xi-Ling; Winter, Jerrold C.; Yu, Ai-Ming (October 2010). "Psychedelic 5-Methoxy-N,N-dimethyltryptamine: Metabolism, Pharmacokinetics, Drug Interactions, and Pharmacological Actions". Current Drug Metabolism. 11 (8): 659–666. ISSN 1389-2002. PMC 3028383free to read. PMID 20942780. 
  4. ^ a b "5-MeO-DMT Timeline". Erowid. 
  5. ^ Krebs-Thomson, Kirsten; Ruiz, ErbertM.; Masten, Virginia; Buell, Mahalah; Geyer, MarkA. (December 2006). "The roles of 5-HT1A and 5-HT2 receptors in the effects of 5-MeO-DMT on locomotor activity and prepulse inhibition in rats". Psychopharmacology. 189 (3): 319–329. doi:10.1007/s00213-006-0566-1. ISSN 0033-3158. PMID 17013638. 
  6. ^ Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako (22 March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101. 
  7. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015. 
  8. ^ "Poisons Standard July 2016". Federal Register of Legislation. 
  9. ^ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor" (PDF). Svensk författningssamling (in Swedish). 7 September 2004. 
  10. ^ "Turkish Law" (PDF). Resmi Gazete. 16 December 2013. 
  11. ^ Drug Enforcement Administration (DEA), Department of Justice (20 December 2010). "Schedules of Controlled Substances: Placement of 5-Methoxy-N,N-Dimethyltryptamine into Schedule I of the Controlled Substances Act" (PDF). Federal Register. 75 (243): 79296–79300. ISSN 0097-6326. PMID 21171485. 

External links[edit]