2,4,5-Trimethoxyamphetamine

Chemical compound

2,4,5-Trimethoxyamphetamine
[[File: Chemical structure of 2,4,5-Trimethoxyamphetamine |frameless|220px|alt=|]]
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2,4,5-Trimethoxyamphetamine (TMA-2) is a psychedelic amphetamine of the substituted amphetamine class. It is a structural analog of mescaline and is known for its psychoactive effects.

Chemical Structure and Properties

2,4,5-Trimethoxyamphetamine is a phenethylamine derivative, characterized by the presence of three methoxy groups attached to the benzene ring at the 2, 4, and 5 positions. The chemical formula is C₁₂H₁₉NO₃, and it has a molecular weight of 225.29 g/mol.

Pharmacology

TMA-2 acts primarily as a serotonin receptor agonist, particularly at the 5-HT_2A receptor, which is believed to be responsible for its psychedelic effects. The compound is known to produce alterations in perception, mood, and cognition, similar to other psychedelics such as LSD and psilocybin.

Effects

The effects of TMA-2 can vary significantly depending on the dose and individual sensitivity. Common effects include visual and auditory hallucinations, altered sense of time, and changes in emotional state. Users may also experience enhanced sensory perception and a feeling of connectedness with their surroundings.

Synthesis

The synthesis of 2,4,5-Trimethoxyamphetamine involves the alkylation of 2,4,5-trimethoxybenzaldehyde with nitroethane, followed by reduction of the resulting nitrostyrene to the corresponding amine. This process requires careful control of reaction conditions to ensure the desired product is obtained.

Legal Status

The legal status of TMA-2 varies by country. In some jurisdictions, it is classified as a controlled substance, making its manufacture, sale, or possession illegal without proper authorization. In others, it may be unscheduled but still subject to regulation under analog laws.

History

TMA-2 was first synthesized by the chemist Alexander Shulgin, who documented its effects in his book PiHKAL: A Chemical Love Story. Shulgin's work in the field of psychedelics has been influential in the study of these compounds and their potential therapeutic applications.

Related Compounds

TMA-2 is part of a family of compounds known as the trimethoxyamphetamines, which also includes 2,4,6-Trimethoxyamphetamine (TMA-6) and 3,4,5-Trimethoxyamphetamine (TMA). These compounds share similar structures and effects but differ in the position of the methoxy groups on the benzene ring.

See Also

• Psychedelic drug
• Phenethylamine
• Alexander Shulgin
• PiHKAL

Related Pages

• Mescaline
• LSD
• Psilocybin