DOI

Chemistry

Also known as

• 64584-34-5
• 4-DOI
• 4-Iodo-2,5-dimethoxyphenylisopropylamine
• 2,5-Dimethoxy-4-iodoamphetamine
• DOI-P
• 1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane
• 2,5-Dimethoxy-4-iodophenylisopropylamine
• 1-(4-Iodo-2,5-dimethoxyphenyl)-2-aminopropane

Stereoisomers

2 distinct stereoisomers are registered for this structure. This area's record is the racemate — the mixture, which is normally the form encountered.

• 2,5-Dimethoxy-4-iodoamphetamine this area mixture CID 1229
• Benzeneethanamine, 4-iodo-2,5-dimethoxy-alpha-methyl-, (alphaS)- CID 6603801
• Benzeneethanamine, 4-iodo-2,5-dimethoxy-alpha-methyl-, (alphaR)- CID 9840090

Attribution

• 

  David E. Nichols — discovered its activity, 1987

  DOI itself was first described by Ronald Coutts and Jerry Malicky in 1973, not by Nichols. Nichols's group, with Chester Mathis, characterised the radioiodinated enantiomers and introduced [125I]DOI as a 5-HT2 agonist radioligand — the reason DOI is a standard laboratory tool today. Included for that contribution only.

  source

• 

  Alexander "Sasha" Shulgin — discovered its activity, 1991

  NOT his synthesis: first described by Ronald Coutts and Jerry Malicky in 1973. Shulgin's PiHKAL entry (#67) is the source of the human dosage and activity data; year given is the PiHKAL publication.

  source