2,5-Dimethoxy-4-iodoamphetamine

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2,5-Dimethoxy-4-iodoamphetamine

Chemical structure of 2,5-Dimethoxy-4-iodoamphetamine
3D animation of DOI molecule

2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine. It is known for its hallucinogenic properties and is used primarily in scientific research.

Chemical Properties

2,5-Dimethoxy-4-iodoamphetamine is a member of the phenethylamine and amphetamine chemical classes. Its chemical formula is C11H16INO2. The compound features a methoxy group at the 2 and 5 positions of the phenyl ring and an iodine atom at the 4 position.

Pharmacology

DOI acts primarily as a serotonin receptor agonist, with a high affinity for the 5-HT2A receptor. This interaction is responsible for its psychedelic effects. The compound is known to induce alterations in perception, mood, and cognition, similar to other psychedelic substances.

Effects

The effects of DOI can include visual and auditory hallucinations, altered sense of time, and changes in thought processes. The onset of effects typically occurs within 30 to 60 minutes after ingestion, with a duration of action lasting up to 16 hours.

Uses

While DOI is not commonly used recreationally due to its long duration and intense effects, it is utilized in scientific research to study the serotonin system and the effects of psychedelics on the brain. It is also used in receptor binding studies to understand the interaction of drugs with the 5-HT2A receptor.

Legal Status

The legal status of DOI varies by country. In some jurisdictions, it is classified as a controlled substance, while in others, it may be legal for research purposes.

Related Compounds

DOI is structurally related to other psychedelic amphetamines such as 2,5-Dimethoxy-4-bromoamphetamine (DOB) and 2,5-Dimethoxy-4-ethylamphetamine (DOET). These compounds share similar pharmacological profiles and effects.

Related Pages

Gallery

  • Chemical structure of 2,5-Dimethoxy-4-iodoamphetamine

  • 3D animation of DOI molecule

  • Chemical structure of 2,5-Dimethoxy-4-iodoamphetamine

  • 3D animation of 2,5-Dimethoxy-4-iodoamphetamine

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Contributors: Prab R. Tumpati, MD