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2,3,5-Trimethoxyamphetamine

Field	Value
drug_name	TMA-4
image	Trimethoxyamphetamine-4.svg
image_class	skin-invert-image
width	250px
routes_of_administration	Oral
class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC_prefix	None
duration_of_action	~6 hours
CAS_number	23693-14-3
PubChem	602804
ChemSpiderID	523988
UNII	LEL94CV318
ChEMBL	103331
synonyms	2,3,5-TMA; TMA-4
IUPAC_name	1-(2,3,5-trimethoxyphenyl)propan-2-amine
C	12	H=19	N=1	O=3
SMILES	CC(CC1=C(C(=CC(=C1)OC)OC)OC)N
StdInChI	1S/C12H19NO3/c1-8(13)5-9-6-10(14-2)7-11(15-3)12(9)16-4/h6-8H,5,13H2,1-4H3
StdInChIKey	MJIBJXKJBRLSQA-UHFFFAOYSA-N

| Drugs.com =

| elimination_half-life =

2,3,5-Trimethoxyamphetamine (2,3,5-TMA), also known as TMA-4, is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the possible positional isomers of trimethoxyamphetamine and is a positional isomer of 3,4,5-trimethoxyamphetamine (TMA or TMA-1).

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2,3,5-TMA's dose as greater than 80mg orally and its duration as perhaps or about 6hours. Based on limited testing, it produced threshold effects including much introspection among others, along with no subjective physical symptoms. The drug at 80mg was described as comparable to 50μg LSD or 120mg TMA and as being roughly 4-fold as potent as mescaline. Per Shulgin, more testing is needed to fully characterize the drug in humans.

Interactions

Pharmacology

Pharmacodynamics

2,3,5-TMA shows affinity for serotonin receptors. The drug substitutes for DOM in rodent drug discrimination tests.

Chemistry

Synthesis

The chemical synthesis of 2,3,5-TMA has been described.

History

2,3,5-TMA was first described in the scientific literature by Alexander Shulgin in 1966. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).

Society and culture

Legal status

Canada

2,3,5-TMA is a controlled substance in Canada under phenethylamine blanket-ban language.

United States

As a positional isomer of 3,4,5-trimethoxyamphetamine (TMA), 2,3,5-TMA is a Schedule I controlled substance in the United States.

References

{{CitePiHKAL https://erowid.org/library/books_online/pihkal/pihkal160.shtml
(2011). "[[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]]". [[Transform Press]].
(1994). "Hallucinogens: An Update". National Institute on Drug Abuse.
(2003). "Hallucinogens: A Forensic Drug Handbook". Elsevier Science.
(1982). "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neuroscience and Biobehavioral Reviews.
(March 1980). "Serotonin receptor affinities of psychoactive phenalkylamine analogues". Journal of Medicinal Chemistry.
(October 1982). "Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines". Pharmacology, Biochemistry, and Behavior.
(May 1966). "The six trimethoxyphenylisopropylamines (trimethoxyamphetamines)". Journal of Medicinal Chemistry.
"Controlled Drugs and Substances Act".

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.

methoxyphenethylamines psychedelic-phenethylamines serotonin-receptor-modulators substituted-amphetamines

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