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5-MeO-2-TMT

Chemical compound

Field	Value
verifiedrevid	413277905
image	5-MeO-2,N,N-TMT.svg
image_class	skin-invert-image
width	200px
image2	5-MeO-2-TMT 3D.png
image_class2	bg-transparent
width2	200px
routes_of_administration	Oral
class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC_prefix	None
legal_DE	NpSG
legal_UK	Class A
duration_of_action	5–10 hours
CAS_number	67292-68-6
UNII_Ref
UNII	XZ2CCP18I2
PubChem	49756
ChemSpiderID_Ref
ChemSpiderID	45143
ChEMBL_Ref
ChEMBL	7143
synonyms	5-Methoxy-2,N,N-trimethyltryptamine; 5-MeO-2,N,N-TMT; 5-MeO-TMT; 2-Methyl-5-methoxy-N,N-dimethyltryptamine; 2-Me-5-MeO-DMT; Indapex; MMDT; 5-Methoxy-2-methyl-DMT
IUPAC_name	2-(5-methoxy-2-methyl-1H-indol-3-yl)-N,N-dimethylethanamine
C	14	H=20	N=2	O=1
SMILES	CC1=C(C2=C(N1)C=CC(=C2)OC)CCN(C)C
StdInChI_Ref
StdInChI	1S/C14H20N2O/c1-10-12(7-8-16(2)3)13-9-11(17-4)5-6-14(13)15-10/h5-6,9,15H,7-8H2,1-4H3
StdInChIKey_Ref
StdInChIKey	ACEHBQPPDDGCGZ-UHFFFAOYSA-N

| elimination_half-life =

5-Methoxy-2,N,N-trimethyltryptamine (5-MeO-2,N,N-TMT, 5-MeO-TMT), also known as 2-methyl-5-methoxy-N,N-dimethyltryptamine (2-Me-5-MeO-DMT), is a serotonin receptor modulator and psychedelic drug of the tryptamine and 2-alkyltryptamine families. It is taken orally.

5-MeO-2-TMT was first synthesized by Alexander Shulgin and reported in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).

Use and effects

According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), 5-MeO-TMT has a dose range of 75 to 150mg orally and a duration of 5 to 10hours. It produces effects including sexual stimulation, enhanced orgasm, relaxation, sedation, tingling, sleep disturbances, chills and cold sensations, time dilation, reduced heart rate, reduced respiratory rate, mild nausea, motor incoordination, visual waviness, mild to pronounced closed-eye visuals, emotional lability, crying, body temperature fluctuations, uncomfortableness, gastrointestinal disturbances, and abdominal pain. It has been said that 5-MeO-TMT at a dose of 150mg is definitely hallucinogenic and can be compared to a moderate 300mg dose of mescaline.

Interactions

Pharmacology

Pharmacodynamics

Target	Ki (nM)
[5-HT1A](5-ht1a-receptor)	200
[5-HT1B](5-ht1b-receptor)	10,000
[5-HT1D](5-ht1d-receptor)	250
[5-HT1E](5-ht1e-receptor)	1,800
[5-HT1F](5-ht1f-receptor)	ND
[5-HT2A](5-ht2a-receptor)	10,000 (rat)
[5-HT2B](5-ht2b-receptor)	ND
[5-HT2C](5-ht2c-receptor)	4,020 (rat)
[5-HT3](5-ht3-receptor)	ND
[5-HT4](5-ht4-receptor)	ND
[5-HT5A](5-ht5a-receptor)	10,450
[5-HT6](5-ht6-receptor)	60–80
[5-HT7](5-ht7-receptor)	145
α1A–α2C	ND
β1–β3	ND
D1–D5	10,000
H1	10,000
H2	ND
H3, H4	10,000
M1–M5	10,000
I1	ND
σ1, σ2	ND
	ND
	10,000
	6,380
	10,000
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:

The affinities of 5-MeO-TMT for numerous targets have been reported. 2-Methyltryptamines like 5-MeO-TMT show a loss of affinity for the serotonin 5-HT2A receptor but retained affinity for the serotonin 5-HT6 receptor. It also retains significant affinity for the serotonin 5-HT1A, 5-HT1D, and 5-HT7 receptors. In contrast to 5-MeO-DMT, 5-MeO-TMT is orally active, suggesting that the 2-methyl group blocks metabolism by monoamine oxidase (MAO).

Chemistry

Synthesis

The chemical synthesis of 5-MeO-2-TMT has been described.

Analogues

2-Methyltryptamine (2-MT or 2-Me-T)
2-Methyl-N,N-diethyltryptamine (2-Me-DET)
2,N,N-Trimethyltryptamine (2,N,N-TMT or 2-Me-DMT)
2,α-Dimethyltryptamine (2,α-DMT or 2-Me-αMT)
5-Methoxy-7,N,N-trimethyltryptamine (5-MeO-7-TMT or 7-Me-5-MeO-DMT)
2-Ethyl-5-methoxy-N,N-dimethyltryptamine (EMDT; 2-Et-5-MeO-DMT)
BGC20-761 (5-MeO-2-phenyl-DMT)

Society and culture

Legal status

Canada

5-MeO-2-TMT is not an explicitly nor implicitly controlled substance in Canada as of 2025.

United States

5-MeO-2-TMT is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

References

(February 2010). "Psychedelics and the human receptorome". PLOS ONE.
(January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev.
(2003). "Hallucinogens: A Forensic Drug Handbook". Elsevier Science.
(March 2000). "2-Substituted tryptamines: agents with selectivity for 5-HT(6) serotonin receptors". J Med Chem.
[http://www.erowid.org/library/books_online/tihkal/tihkal45.shtml Erowid Online Books : "TIHKAL" - #45 5-MEO-TMT]
(26 March 2025). "Kᵢ Database".
(5 December 2025). "Controlled Drugs and Substances Act".
(January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.

Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

2-alkyltryptamines designer-drugs n,n-dialkyltryptamines dimethylamino-compounds 5-methoxytryptamines psychedelic-tryptamines serotonin-receptor-modulators tihkal

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