2,5-Dimethoxy-4-methylamphetamine

2,5-Dimethoxy-4-methylamphetamine

Chemical structure of 2,5-Dimethoxy-4-methylamphetamine

2,5-Dimethoxy-4-methylamphetamine (DOM) is a psychedelic drug and a substituted amphetamine. It is known for its potent hallucinogenic effects and is a member of the phenethylamine class of compounds.

Chemical Structure and Properties

2,5-Dimethoxy-4-methylamphetamine is a substituted amphetamine with the chemical formula C₁₂H₁₉NO₂. It features a methoxy group at the 2 and 5 positions and a methyl group at the 4 position of the phenyl ring. The presence of these groups contributes to its psychoactive properties.

Pharmacology

DOM acts primarily as a serotonin receptor agonist, particularly at the 5-HT_2A receptor. This interaction is responsible for its psychedelic effects, which include altered perception, mood, and cognition. The drug is known for its long duration of action, often lasting 14 to 20 hours.

History and Usage

DOM was first synthesized by Alexander Shulgin in the 1960s. It gained popularity in the 1960s and 1970s as a recreational drug. Shulgin documented its synthesis and effects in his book PiHKAL: A Chemical Love Story.

Effects

The effects of DOM are similar to those of other psychedelics such as LSD and mescaline. Users report visual hallucinations, altered sense of time, and changes in mood and thought patterns. Due to its potency, the effects can be overwhelming, and it is considered a "heavy" psychedelic.

Legal Status

DOM is classified as a Schedule I controlled substance in the United States, meaning it is illegal to manufacture, buy, possess, or distribute without a DEA license. It is similarly controlled in many other countries.

Related Compounds

DOM is part of a family of compounds known as the 2C family, which includes other psychedelics such as 2C-B, 2C-I, and 2C-E. These compounds share a similar chemical structure and mechanism of action.

See Also

• Psychedelic drug
• Phenethylamine
• Alexander Shulgin
• PiHKAL

Gallery

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  3D model of DOM
• Variants of the DOM molecule
  Variants of the DOM molecule