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2,3,4-Trimethoxyamphetamine

Field	Value
drug_name	TMA-3
image	Trimethoxyamphetamine-3.svg
image_class	skin-invert-image
routes_of_administration	Oral
class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC_prefix	None
duration_of_action	Unknown
CAS_number	1082-23-1
PubChem	31012
ChemSpiderID	28771
UNII	9T3SO4A6HM
ChEMBL	30777
synonyms	2,3,4-TMA; TMA-3; α-Methylisomescaline
IUPAC_name	1-(2,3,4-trimethoxyphenyl)propan-2-amine
C	12	H=19	N=1	O=3
SMILES	CC(CC1=C(C(=C(C=C1)OC)OC)OC)N
StdInChI	1S/C12H19NO3/c1-8(13)7-9-5-6-10(14-2)12(16-4)11(9)15-3/h5-6,8H,7,13H2,1-4H3
StdInChIKey	LWDQPPLPHGXYLG-UHFFFAOYSA-N

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| elimination_half-life =

2,3,4-Trimethoxyamphetamine (2,3,4-TMA), also known as TMA-3 or as α-methylisomescaline, is a putative 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 2,3,4-TMA's dose as greater than 100mg orally and its duration as unknown. The drug produced no effects whatsoever at a dose of 100mg in three separate individuals. Higher doses were not tested, but 2,3,4-TMA could possibly be active at higher doses.

Interactions

Pharmacology

Pharmacodynamics

2,3,4-TMA shows affinity for serotonin receptors. It substituted for DOM in rodent drug discrimination tests.

Chemistry

Synthesis

The chemical synthesis of 2,3,4-TMA has been described.

History

2,3,4-TMA was first described in the scientific literature by Alexander Shulgin in 1964. 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

2,3,4-TMA is a controlled substance in Canada under phenethylamine blanket-ban language.

United States

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

References

{{CitePiHKAL https://erowid.org/library/books_online/pihkal/pihkal159.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.
(August 2000). "Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors". Drug and Alcohol Dependence.
(October 1982). "Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines". Pharmacology, Biochemistry, and Behavior.
(July 1964). "Psychotomimetic amphetamines: methoxy 3,4-dialkoxyamphetamines". Experientia.
(May 1966). "The six trimethoxyphenylisopropylamines (trimethoxyamphetamines)". Journal of Medicinal Chemistry.
"Controlled Drugs and Substances Act".

Info: Wikipedia Source

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

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