3,4,5-Trimethoxyamphetamine

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A psychoactive drug of the phenethylamine and amphetamine chemical classes

3,4,5-Trimethoxyamphetamine





Chemical nomenclature
IUPAC name 1-(3,4,5-Trimethoxyphenyl)propan-2-amine



Routes Oral






Legal status Uncontrolled
Identifiers
CAS Number 2234-16-4
PubChem 4446


ChemSpider 4291
UNII 0F5N573A2Y


ChEMBL 2104660
Chemical data


Chemical formula C12H19N1O3


SMILES CC(Cc1cc(OC)c(OC)c(OC)c1)N
InChI 1S/C12H19NO3/c1-8(13)6-9-7-10(14-2)12(16-4)11(15-3)5-9/h5,7-8H,6,13H2,1-4H3
InChIKey ZJZLZVYVQYJXHL-UHFFFAOYSA-N
File:Trimethoxyamphetamine.svg
Trimethoxyamphetamine structure

3,4,5-Trimethoxyamphetamine (TMA) is a psychoactive drug of the phenethylamine and amphetamine chemical classes. It is known for its hallucinogenic effects and is structurally related to other psychedelic compounds such as mescaline.

Chemical structure and properties[edit]

3,4,5-Trimethoxyamphetamine is a substituted amphetamine, characterized by the presence of three methoxy groups attached to the benzene ring of the amphetamine backbone. The chemical formula is C12H19NO3, and it has a molecular weight of 225.29 g/mol.

Pharmacology[edit]

TMA acts primarily as a serotonin receptor agonist, particularly at the 5-HT2A receptor, which is believed to be responsible for its psychedelic effects. The compound also has affinity for other serotonin receptors, contributing to its overall psychoactive profile.

Effects[edit]

The effects of 3,4,5-Trimethoxyamphetamine are similar to those of other psychedelic drugs, including altered perception, mood, and cognition. Users may experience visual hallucinations, changes in thought patterns, and an altered sense of time. The intensity and duration of effects can vary based on dosage and individual sensitivity.

History and usage[edit]

TMA was first synthesized by the chemist Alexander Shulgin, who documented its effects in his book PiHKAL: A Chemical Love Story. It has been used primarily in research settings to study the effects of psychedelics on the human mind.

Legal status[edit]

3,4,5-Trimethoxyamphetamine is not a controlled substance in many countries, but its legal status can vary. It is important to check local regulations before acquiring or using this compound.

Related compounds[edit]

See also[edit]

Related pages[edit]

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