5-MeO-DMT

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5-MeO-DMT
Systematic (IUPAC) name
2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
Identifiers
CAS number	1019-45-0
ATC code	?
PubChem	1832
Chemical data
Formula	C13H18N2O
Mol. mass	218.298 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Class A(UK) Schedule I(US)
Routes	Smoked, Insufflated

5-MeO-DMT is a very 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.

Contents 1 Chemistry 2 History 3 Use and effects 3.1 Positive 3.2 Neutral 3.3 Negative 4 Legality 4.1 International Law 4.1.1 Denmark 4.1.2 Germany 4.1.3 Greece 4.1.4 New Zealand 4.1.5 Sweden 4.1.6 Switzerland 4.2 US State Law 4.2.1 Nebraska 4.2.2 S. Dakota 5 See also 6 External links 7 References

[edit] 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 player in the psychoactive effects of the snuff. However, recent tests confirm that bufotenin is the main active psychoactive ingredient of Yopo and that DMT and 5-MeO-DMT are present in quantities too small to elicit much effects.^[1] It occurs in many organisms that contain bufotenin(e) (5-hydroxy-DMT), and is the O-methyl analogue of that compound.

[edit] 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.

[edit] Use and effects

This section may contain original research or unverified claims. Please help Wikipedia by adding references. See the talk page for details.(October 2007)

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 an 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 a 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.^[2]
Some report the effects to be unpleasant causing nausea and the feeling of being "sat on by an elephant".^[3]

Erowid lists the following effects for smoked 5-MeO-DMT:^[2]

[edit] 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

[edit] 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

[edit] Negative

• overly-intense experiences
• nausea^[3]
• sense of pressure in the body^[3]
• 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)

[edit] Legality

[edit] International Law

[edit] Denmark

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

[edit] 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)

[edit] Greece

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

[edit] New Zealand

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

[edit] Sweden

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

[edit] Switzerland

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

[edit] US State Law

[edit] Nebraska

Schedule I (Reference)

[edit] S. Dakota

Schedule I : 5-methoxy-N, N-Dimethyltryptamine. Feb 2003

[edit] See also

• 5-MeO-AMT
• 5-MeO-DIPT
• Bufotenin (5-OH-DMT)
• List of Entheogens
• Psychedelic plants

[edit] External links

• TiHKAL #38 on Erowid
• Erowid's 5-MeO-DMT Vault

[edit] References

1. ^ Pharmanopo-Psychonautics: Human Intranasal, Sublingual, Intrarectal, Pulmonary and Oral Pharmacology of Bufotenine by Jonathan Ott, The Journal of Psychoactive Drugs, September 2001
2. ^ ^{a b} Erowid. Effects.
3. ^ ^{a b c} Psychecelic Chemistry by Michael Valentine Smith, Page 40, ISBN 0915179105

v • d • e Drugs from TiHKAL AL-LAD • DBT • DET • DiPT • 5-MeO-α-MT • DMT • 2,α-DMT • α,N-DMT • DPT • EiPT • α-ET • ETH-LAD • Harmaline • Harmine • 4-HO-DBT • 4-HO-DET • 4-HO-DiPT • 4-HO-DMT • 5-HO-DMT • 4-HO-DPT • 4-HO-MET • 4-HO-MiPT • 4-HO-MPT • 4-HO-pyr-T • Ibogaine • LSD • MBT • 4,5-MDO-DiPT • 5,6-MDO-DiPT • 4,5-MDO-DMT • 5,6-MDO-DMT • 5,6-MDO-MiPT • 2-Me-DET • 2-Me-DMT • Melatonin • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 4-MeO-MiPT • 5-MeO-MiPT • 5,6-MeO-MiPT • 5-MeO-NMT • 5-MeO-pyr-T • 6-MeO-THH • 5-MeO-TMT • 5-MeS-DMT • MiPT • α-MT • NET • NMT • PRO-LAD • pyr-T • Tryptamine • Tetrahydroharmine • α,N,O-TMS

v • d • e Psychedelic tryptamines α,N,N-TMT • 2,N,N-TMT • 5,N,N-TMT • 4-Acetoxy-DMT • 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-HO-5-MeO-DMT • α-ET • α-MT • Baeocystin • Bufotenin • DBT • DET • DIPT • DMT • DPT • EiPT • PiPT • Ethocin • Ethocybin • Iprocin • 4-HO-MET • 4-HO-MiPT • MET • MIPT • 5-Me-MIPT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-MET • 5-MeO-MIPT • 5-MeO-α,N,N-TMT • 5-MeO-2,N,N-TMT • Miprocin • Norbaeocystin • Psilocin • Psilocybin

v • d • e Tryptamines 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-HO-DIPT • 5-Bromo-DMT • 5-Fluoro-α-MT • 5-MeO-α-ET  • 5-MeO-α-MT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-MIPT • α-ET • α-MT • Aeruginascin • Baeocystin • Bufotenin • DET • DiPT • DMT • DPT • Ethocybin • EiPT • Ethocin • Ibogaine • Iprocin • MET • MiPT • Miprocin • Melatonin • NMT • Norbaeocystin • Normelatonin • PiPT • Psilocin • Psilocybin • Rizatriptan • Serotonin • Sumatriptan • Tryptamine • Tryptophan