5-MeO-DMT

5-MeO-DMT
Systematic (IUPAC) name
2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
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 powerful psychedelic tryptamine. It is found in a wide variety of plant species, and a single psychoactive toad species. Like its close relatives DMT and bufotenin (5-HO-DMT), it has been used as an entheogen by South American shamans for thousands of years.[1]

Chemistry

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—sometimes nonexistent—quantity contained within the seeds of this plant, which instead achieve their psychoactivity due to the bufotenin that they contain.[2] It occurs in many organisms that contain bufotenin (5-HO-DMT), and is the O-methyl analogue of that compound. It is metabolized mainly by CYP2D6.[3]

History

Traditionally 5-MeO-DMT has been used in psychedelic snuff made from virola bark resin, and may be a trace constituent of ayahuasca when plants such as Diplopterys cabrerana are used as an admixture. 5-MeO-DMT is also found in the venom of the Colorado River toad (Incilius alvarius [= Bufo alvarius]), although there was no direct evidence this was used as a hallucinogen until recent times.

Religious use

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 members of the Church of the Tree of Life from Inner Center and after 1986 was also available to some other religious groups from Inner Center.[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] A member of the Church of the Tree of Life estimates there were fewer than 6,000 active members in 1979.[5]

Pharmacology

5-MeO-DMT is a methoxy derivative of DMT. Its pharmacological action is mainly through serotonin (5-HT) receptors. Specifically, this molecule shows high affinity for the 5-HT2 and 5-HT1A subtypes.[6] Additional mechanisms of action such as inhibition of monoamine reuptake may be involved also.[7] 5-MeO-DMT is O-demethylated by polymorphic cytochrome P450 2D6 (CYP2D6) to an active metabolite, bufotenin.[8]

Use and effects

Incilius alvarius, which has 5-MeO-DMT in its venom and skin.

When used as a drug in its purified form, 5-MeO-DMT is vaporized, insufflated, or injected and is active at a dose of as little as 2 mg. 5-MeO-DMT is active orally when taken with a MAOI, but according to numerous reports the combination with MAOI is extremely unpleasant and has a strong body load. Additional mechanisms of action — such as MAO inhibition — may also be involved as, according to the researcher Jonathan Ott, 5-MeO-DMT was active orally for him in a 30 mg dose without aid of a MAOI.[9]

The onset of effects occurs within seconds after vaporizing/injecting, or minutes after insufflating, and the experience is sometimes described as similar to a near-death experience. Peak effects last for approximately 5–10 minutes when vaporized. When insufflated, the peak effects are considerably less intense, but last for 15–25 minutes on average.

Although similar in many respects to its close relatives DMT and bufotenin (5-HO-DMT), the effects are typically not as visual. This confusion can become extremely dangerous because the recommended dosage for 5-MeO-DMT is much smaller than that or DMT (about 1/10 to 1/2 of a smaller dose).[10] Some users report experiencing no visual effects from it even at very high doses.[11] Some report the effects to be unpleasant causing nausea and the feeling of being "sat on by an elephant".[12]

Erowid lists the following effects for vaporized 5-MeO-DMT:[11]

Desired

Neutral

Undesired

Legality

China

As of October 2015 5-MeO-DMT is a controlled substance in China.[13]

Australia

5-MeO-DMT is an analogue of N,N-Dimethyltryptamine making it a schedule 9 prohibited substance under the Poisons Standard (October 2015).[14] A schedule 9 drug is outlined in the Poisons Act 1964 as "Substances 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 the CEO." [15]

Denmark

As of December 1, 2004, 5-MeO-DMT was legally restricted to "medical or scientific purposes". See EMCDDA.

Germany

Schedule I / Highest level of control, unable to be prescribed, manufactured, or possessed as of Sep, 1999. (listed as [2-(5-Methoxyindol-3-yl)ethyl]dimethylazan)[16]

Greece

5-MeO-DMT became a controlled substance in Greece on February 18, 2003 [EU Legal Database].

New Zealand

5-MeO-DMT is Schedule I (Class A) in New Zealand.

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 5-MeO-DMT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Oct 1, 2004, in their regulation SFS 2004:696 listed as 5-metoxi-N,N-dimetyltryptamin (5-MeO-DMT), making it illegal to sell or possess.[17]

Switzerland

5-MeO-DMT is Schedule I in Switzerland.

Turkey

5-MeO-DMT is forbidden in Turkey since 16 December 2013.[18]

US federal law

On August 21, 2009, the Drug Enforcement Administration issued a Notice of Proposed Rulemaking to initiate placing 5-MeO-DMT into Schedule I of the Controlled Substances Act (the most restrictive category).[19] Comment DEA-2009-0008-0007.1 requested a 180-day extension of the period for public comment and requests for hearings, objected to the proposed rule on multiple grounds including Constitutional issues, identified the submitter as a person who would be "adversely affected and aggrieved by the proposed ruling" and requested an exemption for religious use if DEA did place 5-MeO-DMT in Schedule I "as an attempt to define and clarify some legal issues."[5]

On September 29 and 30, 2009, the DEA posted the Supporting & Related Materials for the NPRM while retaining the September 21, 2009 Due date for comments.[20]

On October 28, 2009 DEA reopened the period for public comment because it had not posted two Supporting & Related Materials documents online during the original period for public comment. Documents and comments were split between Docket ID: DEA-2009-0008 and Docket ID: DEA-2009-0013 in a manner which creates difficulty and in viewing all documents and determining where and how to submit comments online. The two Supporting & Related Materials documents were not posted to Docket ID: DEA-2009-0013 until November 3, 2009 but the 30 day period for public comment was not changed from November 27, 2009.[21]

5-MeO-DMT was added to Schedule I, effective January 19, 2011. This means it is illegal to manufacture, buy, possess, or distribute (sell, trade or give) without a DEA license.[22]

See also

References

  1. ↑ http://www.dmtsite.com/5-meo-dmt/information/traditional_use.html Short summary of 5-MeO-DMT use among shamans
  2. ↑ Anadenanthera: Visionary Plant of Ancient South America by Constantino M. Torres and David B. Repke
  3. ↑ Shen HW, Jiang XL, Winter JC, Yu AM. (Oct 2010), "Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions", Current Drug Metabolism 11 (8): 659–66, doi:10.2174/138920010794233495, PMC 3028383, PMID 20942780
  4. 1 2 "5-Meo-DMT Timeline". Erowid.org.
  5. 1 2 "DEA-2009-0008-0007.1".
  6. ↑ Krebs-Thomson, Kirsten; Ruiz, Erbert M.; Masten, Virginia; Buell, Mahalah; Geyer, Mark A. (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.
  7. ↑ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology 559 (2-3): 132–7. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  8. ↑ "Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions". Curr Drug Metab 11 (8): 659–66. Oct 1, 2011. doi:10.2174/138920010794233495. PMC 3028383. PMID 20942780.
  9. ↑ Shamanic Snuffs or Entheogenic Errhines by Jonathan Ott
  10. ↑ "Erowid 5-MeO-DMT Vault: Basics". www.erowid.org. Retrieved 2015-12-17.
  11. 1 2 "Effects". Erowid.org.
  12. 1 2 3 Michael Valentine Smith (1981). Psychedelic Chemistry. Loompanics Unlimited. p. 40. ISBN 0-915179-10-5.
  13. ↑ "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.
  14. ↑ Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534
  15. ↑ Poisons Act 1964 http://www.slp.wa.gov.au/pco/prod/FileStore.nsf/Documents/MRDocument:26063P/$FILE/Poisons%20Act%201964%20-%20%5B09-f0-04%5D.pdf?OpenElement
  16. ↑ see Deutsche BtMG or http://www.silicium-sensei.de/projecte/drugs/news/news.html
  17. ↑ http://www.notisum.se/rnp/sls/sfs/20040696.pdf
  18. ↑ Link to Turkish Law http://www.resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf
  19. ↑ DEA. "Placement of 5-Methoxy-N,N-Dimethyltryptamine Into Schedule I of the Controlled Substances Act by DEA, August 2009".
  20. ↑ "DEA-2009-0008".
  21. ↑ "DEA-2009-0013".
  22. ↑ "DEA_FRDOC_0001-0076".

External links

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