Anodyne

DOI
2,5-Dimethoxy-4-iodoamphetamine
Salts
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2,5-Dimethoxy-4-iodoamphetamine hydrochloride
2,5-Dimethoxy-4-iodoamphetamine hydrochloride
Molecular structure via molpic
Conformer structure via 3Dmol.js
Molecular formulaC11H16INO2[1]
Molecular mass321.15 g/mol[1]
Predicted LogP2.5[1]
Chiralityracemic[2]
Identifiers
[]
IUPAC name1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine[1]
SMILESCC(CC1=CC(=C(C=C1OC)I)OC)N[1]
InChIInChI=1S/C11H16INO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3[1]
InChIKeyBGMZUEKZENQUJY-UHFFFAOYSA-N[1]
Dosing

2,5-Dimethoxy-4-iodoamphetamine

2,5-Dimethoxy-4-iodoamphetamine (also known as 4-DOI, 4-Iodo-2,5-dimethoxyphenylisopropylamine, 2,5-Dimethoxy-4-iodophenylisopropylamine, 1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane, 1-(4-Iodo-2,5-dimethoxyphenyl)-2-aminopropane, 4-Iodo-2,5-dimethoxyamphetamine, 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine, DOI-P, -1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane or Racemic DOI) is a psychedelic substance of the 2,5-dimethoxyphenethylamine class.

Chemistry

2,5-Dimethoxy-4-iodoamphetamine is typically found in the form of its hydrochloride salt.

Stereochemistry

(RS)-2,5-Dimethoxy-4-iodoamphetamine is a racemic mixture of the optical stereoisomers

See also

References

  1. National Center for Biotechnology Information. PubChem Compound Summary for CID 1229, 2,5-Dimethoxy-4-iodoamphetamine. Accessed June 17, 2025. https://pubchem.ncbi.nlm.nih.gov/compound/1229.

  2. U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. 2,5-Dimethoxy-4-iodoamphetamine. UNII: OOM10GW9UE. Global Substance Registration System. Accessed June 17, 2025. https://gsrs.ncats.nih.gov/ginas/app/beta/substances/OOM10GW9UE

  3. Anvisa. RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial. Diário Oficial da União. July 24, 2023. Accessed June 17, 2025. https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451