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2,3,6-Trimethoxyamphetamine

Field	Value
drug_name	TMA-5
image	Trimethoxyamphetamine-5.svg
image_class	skin-invert-image
width	175px
routes_of_administration	Oral
class	Serotonergic psychedelic; Hallucinogen; Stimulant
ATC_prefix	None
duration_of_action	8–10 hours
CAS_number	20513-16-0
PubChem	31013
ChemSpiderID	28772
UNII	E0NJ557A3E
ChEMBL	125134
synonyms	2,3,6-TMA; TMA-5
IUPAC_name	1-(2,3,6-trimethoxyphenyl)propan-2-amine
C	12	H=19	N=1	O=3
SMILES	CC(CC1=C(C=CC(=C1OC)OC)OC)N
StdInChI	1S/C12H19NO3/c1-8(13)7-9-10(14-2)5-6-11(15-3)12(9)16-4/h5-6,8H,7,13H2,1-4H3
StdInChIKey	OASZJWLOOFXASO-UHFFFAOYSA-N

| Drugs.com =

| elimination_half-life =

2,3,6-Trimethoxyamphetamine (2,3,6-TMA), also known as TMA-5, is a psychedelic drug and mild stimulant 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 2,3,6-TMA's dose as approximately 30mg or more orally and its duration as 8 to 10hours. Based on limited testing, the effects of 2,3,6-TMA were reported to include intense introspection, mild stimulation, and pupil dilation, among others. The drug was said to be comparable to about 75μg or more LSD. It is approximately 10times more potent than mescaline. However, it was noted that more testing was needed.

Interactions

Pharmacology

Pharmacodynamics

Unlike the other TMA isomers, 2,3,6-TMA was not tested at serotonin receptors or in rodent drug discrimination tests.

Chemistry

Synthesis

The chemical synthesis of 2,3,6-TMA has been described.

History

2,3,6-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

2,3,6-TMA is a controlled substance in Canada under phenethylamine blanket-ban language.

United States

As a positional isomer of 3,4,5-trimethoxyamphetamine (TMA), 2,3,6-TMA is a Schedule I controlled substance in the United States.

References

{{CitePiHKAL https://erowid.org/library/books_online/pihkal/pihkal161.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.
(June 1986). "Discriminative stimulus properties of phenylisopropylamine derivatives". Drug and Alcohol Dependence.
(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

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methoxyphenethylamines psychedelic-phenethylamines stimulants substituted-amphetamines

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