5-MeO-DMT

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5-MeO-DMT
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Systematic (IUPAC) name
2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
Clinical data
Routes of
administration		 Smoked, Insufflated
Legal status
Legal status
Identifiers
CAS Number 1019-45-0
PubChem CID 1832
IUPHAR/BPS 145
ChemSpider 1766
Chemical data
Formula C13H18N2O
Molar mass 218.298 g/mol[[Script error: No such module "String".]]
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5-MeO-DMT (5-methoxy-dimethyltryptamine) is a powerful psychedelic tryptamine. It is found in a wide variety of plant and psychoactive toad species, and like its close relatives DMT and bufotenin (5-OH-DMT), it has been used as an entheogen by South American shamans for thousands of years.

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. It occurs in many organisms that contain bufotenin(e) (5-hydroxy-DMT), and is the O-methyl analogue of that compound.

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 (Bufo alvarius), although there is no direct evidence this was used as a hallucinogen until recent times.

Religious Use

Traditional


Modern

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.[1] 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.[1] A member of the Church of the Tree of Life estimates there were less than 6000 active members in 1979.[2]

Use and effects

File:Bufo alvarius1.jpg
Bufo alvarius, which has 5-MeO-DMT in its venom and skin.

When used as a drug in its purified form, 5-MeO-DMT is smoked, insufflated, or injected and is active at a dose of as little as 2 mg. 5-MeO-DMT is also active orally, when taken with a monoamine oxidase inhibitor, but according to numerous reports, the combination with MAOI is extremely unpleasant and has a strong body load. According to the researcher Jonathan Ott, 5-MeO-DMT is active orally with doses over 30 mg without aid of an MAOI.

The onset of effects occurs within seconds after smoking/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 smoked. 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-OH-DMT), the effects are typically not as visual. Some users report experiencing no visual effects from it even at very high doses.[3]
Some report the effects to be unpleasant causing nausea and the feeling of being "sat on by an elephant".[4]

Erowid lists the following effects for smoked 5-MeO-DMT:[3]

Positive

  • immersive experiences
  • powerful "rushing" sensation
  • radical perspective shifting
  • profound life-changing spiritual experiences
  • some people experience erotic / sensual enhancement
  • occasional euphoria
  • internal visions (actual visual effects not as common)
  • journey into mind

Neutral

  • short duration
  • change in perception of time
  • experience of "the void"
  • lack of memory of experience
  • muscle jerking, twitching, abnormal vocalizations
  • unconsciousness / nonresponsiveness lasting 5-20 minutes
  • dissociation

Negative

  • overly-intense experiences
  • nausea[4]
  • sense of pressure in the body[4]
  • hard on the lungs to smoke
  • difficulty integrating experiences
  • fear, terror and panic
  • dysphoria (bad feelings)
  • fast onset and intensity can lead to problems if not prepared (dropped pipe, knocking things over, falling & hitting head, etc)

Legality

International Law

Denmark

As of December 1, 2004, 5-MeO-DMT is 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) (see Deutsche BtMG or http://www.silicium-sensei.de/projecte/drugs/news/news.html)

Greece

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

New Zealand

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

Sweden

Controlled in Sweden as of Oct 1, 2004 (see notisum.se)

Switzerland

5-MeO-DMT is Schedule I in Switzerland. [unconfirmed]

Romania

5-MeO-DMT is illegal in Romania since feb 2010.

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).[5] 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."[2]

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.[6]

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.[7]

US State Law

Nebraska

Schedule I[8]

Oklahoma

Schedule I[9]

S. Dakota

Schedule I[10]

See also

References

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External links

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2-Methyl-5-HT • 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-HO-αMT • 4-HO-DIPT • 4-HO-MET • 4-MeO-DMT • 4-Methyl-αET • 4-Methyl-αMT • 5-Benzyloxytryptamine • 5-Bromo-DMT • 5-Carboxamidotryptamine • 5-Fluoro-αMT • 5-HO-αMT • 5-HTP • 5-Fluoro-DMT • 5-Methyl-DMT • 5-Methoxytryptamine • 5-MeO-7,N,N-TMT • 5-MeO-αET  • 5-MeO-αMT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-MIPT • 5,7-Dihydroxytryptamine • 7-Methyl-αET • 7-Methyl-DMT • αET • αMT • Aeruginascin • AL-37350A • BW-723C86 • Baeocystin • Bufotenidine • Bufotenin • DALT • Desformylflustrabromine • DET • DiPT • DMT • DPT • Ethocybin • EiPT • EMDT • Ethocin • FGIN-127 • FGIN-143 • Ibogaine • Iprocin • MET • MiPT • Miprocin • Melatonin • MS-245 • NAS • NMT • Norbaeocystin • Normelatonin • Oxypertine • PiPT • Psilocin • Psilocybin • Rizatriptan • Serotonin • Sumatriptan • Tryptamine • Tryptophan • Yohimbine • Yuremamine • Zolmitriptan

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cs:5-MeO-DMT

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  1. ↑ 1.0 1.1 Erowid. "Erowid 5-Meo-DMT Timeline". 
  2. ↑ 2.0 2.1 "DEA-2009-0008-0007.1". 
  3. ↑ 3.0 3.1 Erowid. "Effects". 
  4. ↑ 4.0 4.1 4.2 Psychedelic Chemistry by Michael Valentine Smith, Page 40, ISBN 0915179105
  5. ↑ DEA-2009-0008. "Placement of 5-Methoxy-N,N-Dimethyltryptamine Into Schedule I of the Controlled Substances Act by DEA, August 2009". 
  6. ↑ "DEA-2009-0008". 
  7. ↑ "DEA-2009-0013". 
  8. ↑ "Statutes Relating to Pharmacy" (PDF). Nebraska Health and Human Services System. 2005. Retrieved 2008-07-04. 
  9. ↑ "Section 2-204 - Schedule I". 
  10. ↑ "SB 25 revise the schedule of certain controlled..." 
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