5-MeO-DMT

5-MeO-DMT
	File:5-MeO-DMT.png
	File:5-MeO-DMT-3d-sticks.png
Clinical data
Routes of; administration	Smoked, Insufflated
Legal status
Legal status	UK: Class A ; US: Schedule I ;
Identifiers
	IUPAC name 2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine;
CAS Number	1019-45-0;
PubChem CID	1832;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C13H18N2O
Molar mass	218.298 g/mol
3D model (JSmol)	Interactive image;
	SMILES CN(C)CCC1=CNC2=C1C=C(C=C2)OC;

5-MeO-DMT is a very powerful psychedelic tryptamine. It is found in a wide variety of plant and 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. 5-MeO-DMT is sometimes referred to as "Businessman's Trip" due to its short duration.^{[citation needed]}

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.

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.

Use and effects

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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 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 in 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]

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^[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)

Legality

International Law

Denmark

As of December 1, 2004, 5-MeO-DMT is legally restricted to "medical or scientific purposes". See EMCDDA. (Thanks Vman and Ali)

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]

US State Law

Nebraska

Schedule I (Reference)

S. Dakota

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

External links

References

↑ Pharmanopo-Psychonautics: Human Intranasal, Sublingual, Intrarectal, Pulmonary and Oral Pharmacology of Bufotenine by Jonathan Ott, The Journal of Psychoactive Drugs, September 2001
↑ ^2.0 ^2.1 Erowid. "Effects".
↑ ^3.0 ^3.1 ^3.2 Psychecelic Chemistry by Michael Valentine Smith, Page 40, ISBN 0915179105

Template:TiHKAL Template:Hallucinogenic tryptamines Template:Tryptamines fi:5-MeO-DMT

Template:WikiDoc Sources

[PharmanopoPsychonautics-1] Pharmanopo-Psychonautics: Human Intranasal, Sublingual, Intrarectal, Pulmonary and Oral Pharmacology of Bufotenine by Jonathan Ott, The Journal of Psychoactive Drugs, September 2001

[Erowid-2] 2.0 ^2.1 Erowid. "Effects".

[Psychecelic_Chemistry_Page_40-3] 3.0 ^3.1 ^3.2 Psychecelic Chemistry by Michael Valentine Smith, Page 40, ISBN 0915179105

[1]

[2]

[3]