2,4-Dimethoxyamphetamine

Chemical compound

2,4-Dimethoxyamphetamine
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2,4-Dimethoxyamphetamine (2,4-DMA) is a psychedelic and stimulant drug of the amphetamine class. It is a derivative of amphetamine and is structurally related to other psychedelic phenethylamines.

Chemical structure and properties

2,4-Dimethoxyamphetamine is a substituted amphetamine, which means it is an amphetamine molecule with additional chemical groups attached. Specifically, it has two methoxy groups (–OCH₃) attached to the benzene ring at the 2 and 4 positions. This structural modification is responsible for its unique pharmacological properties compared to other amphetamines.

Chemical structure of 2,4-Dimethoxyamphetamine

The chemical formula of 2,4-DMA is C₁₁H₁₇NO₂, and it has a molecular weight of 195.26 g/mol. The presence of the methoxy groups increases the lipophilicity of the molecule, potentially affecting its ability to cross the blood-brain barrier.

Pharmacology

2,4-DMA acts primarily as a serotonin and dopamine releasing agent, similar to other psychedelic amphetamines. It is believed to exert its effects by increasing the levels of these neurotransmitters in the synaptic cleft, leading to altered perception, mood, and cognition.

The psychedelic effects of 2,4-DMA are thought to be mediated by its action on the 5-HT2A receptor, a subtype of the serotonin receptor that is known to play a key role in the effects of classic psychedelics such as LSD and psilocybin.

Effects

The effects of 2,4-DMA are not well-documented, but it is expected to produce effects similar to other psychedelic amphetamines, such as 2,5-dimethoxy-4-methylamphetamine (DOM) and 3,4-methylenedioxyamphetamine (MDA). These effects may include:

• Altered sensory perception
• Enhanced mood
• Increased energy and alertness
• Visual and auditory hallucinations
• Changes in thought patterns

Legal status

The legal status of 2,4-DMA varies by country. In some jurisdictions, it may be classified as a controlled substance due to its structural similarity to other regulated amphetamines. In others, it may not be specifically scheduled, but could still be subject to regulation under analog laws.

Synthesis

The synthesis of 2,4-DMA involves the alkylation of 2,4-dimethoxybenzaldehyde with nitroethane, followed by reduction of the resulting nitrostyrene to the corresponding amine. This process is similar to the synthesis of other substituted amphetamines and requires careful control of reaction conditions to ensure the desired product is obtained.

Related compounds

2,4-DMA is part of a larger family of substituted amphetamines, which includes:

• 2,5-Dimethoxy-4-methylamphetamine (DOM)
• 3,4-Methylenedioxyamphetamine (MDA)
• 3,4-Methylenedioxymethamphetamine (MDMA)

These compounds share similar structural features and pharmacological profiles, but differ in their specific effects and potency.

Related pages

• Amphetamine
• Psychedelic drug
• Serotonin receptor