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5-MeO-DMT
General
Systematic name	2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
Other names	5-Methoxy-N,N-dimethyltryptamine; 5-methoxy-3-[2-(dimethylamino)ethyl]indole
Molecular formula	C13H18N2O
SMILES	COC1=CC2=C(NC=C2CCN(C)C)C=C1
Molar mass	218.298 g/mol
Appearance	?
CAS number	[?-?-?]
Properties
Density and phase	? g/cm³, ?
Solubility in water	? g/100 ml (?°C)
Melting point	?°C (? K)
Boiling point	?°C (? K)
Acidity (pKa)	?
Basicity (pKb)	?
Chiral rotation [α]D	?°
Viscosity	? cP at ?°C
Structure
Molecular shape	?
Coordination geometry	?
Crystal structure	?
Dipole moment	? D
Hazards
MSDS	External MSDS
Main hazards	?
NFPA 704
Flash point	?°C
R/S statement	R: ? S: ?
RTECS number	?
Related compounds
Related compounds	?
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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 relative 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 See Also 5 External links 6 References

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 Yopo snuff.

Traditionally 5-MeO-DMT has been used as a psychedelic snuff, such as Yopo or Vilca, 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.

When used as a drug in its purified form, 5-MeO-DMT is smoked, insuffilated, or injected and is active at a dose of as little as 2mg. 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 bodyload. According to the researcher Jonathan Ott, 5-MeO-DMT is active orally with doses over 30mg without aid of an 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.

Erowid lists the following effects for smoked 5-MeO-DMT:^[1]

• short duration
• 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)
• journy into mind

• 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

• overly-intense experiences
• 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)

• 5-MeO-AMT
• 5-MeO-DIPT

• TiHKAL #38 on Erowid
• Erowid's 5-MeO-DMT Vault
• Links to external chemical sources

1. ^ Erowid. Effects.