2,5-Dimethoxy-4-iodoamphetamine

DOI
Chemical structure of (R)-DOI.
Clinical data
Other namesDOI; 2,5-Dimethoxy-4-iodoamphetamine; 4-Iodo-2,5-dimethoxyamphetamine
Routes of
administration		Oral
Drug classSerotonergic psychedelic; Hallucinogen; Serotonin 5-HT2 receptor agonist; Anti-inflammatory agent
ATC code
  • None
Legal status
Legal status
Identifiers
IUPAC name
  • 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine
CAS Number
  • 64584-34-5 Y[correct]
    82864-06-0 ((R)-DOI)
    99665-04-0 ((S)-DOI)
    42203-78-1 (HCl)
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H16INO2
Molar mass321.158 g·mol−1
3D model (JSmol)
Melting point201.5 °C (394.7 °F) (hydrochloride)
Solubility in water10 mg/mL[2]
SMILES
  • IC(C=C1OC)=C(OC)C=C1CC(C)N
InChI
  • InChI=1S/C11H16INO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3 Y
  • Key:BGMZUEKZENQUJY-UHFFFAOYSA-N Y
  (verify)

2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug of the amphetamine and 4-substituted-2,5-dimethoxyamphetamine (DOx) families.[3][4] It is relatively little-used as a recreational drug but is frequently used in scientific research in the study of psychedelics and serotonin receptors.[3][4]

DOI acts as a potent serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A and 5-HT2C receptors.[3][4] The compound has a stereocenter, and R-(−)-DOI is the more active stereoisomer. [125I]-R-(−)-DOI is used as a radioligand and indicator of the presence of serotonin 5-HT2A receptors in studies.[3]

DOI's effects have been compared to LSD, although there are differences that experienced users can distinguish. Besides the longer duration of DOI compared to LSD, the trip tends to be more energetic than an LSD trip, with more body load and a different subjective visual experience. The after effects include residual stimulation and difficulty sleeping, which, depending on the dose, may persist for days.[5] While rare, DOI has sometimes been sold as a substitute for LSD, or even sold falsely as LSD, which may be dangerous because DOI does not have the same established safety profile as LSD.[6] Owing to their very long durations, which users tend to find disagreeable however, DOI and other DOx psychedelics have seen very little recreational use.[3][7][8][9][10]

DOI was first synthesized in 1973, by Coutts and Malicky.[3] Unlike many other psychedelic drugs, DOI is not an explicitly controlled substance in the United States.[11] However, it could be considered a controlled substance under the Federal Analog Act. In any case, its non-controlled status has made DOI usefully accessible for use in scientific research, which has contributed to its popularity for such uses.[3] In December 2023, the Drug Enforcement Agency (DEA) proposed making DOI a schedule I controlled substance.[12] This proposal has been opposed by psychedelic researchers and the DEA has consequently delayed its June 2024 hearing on the proposal.[13]

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ "D101 DOI hydrochloride ≥98% (HPLC), solid". Retrieved 13 April 2008.
  3. ^ a b c d e f g Glennon RA, Dukat M (June 2024). "1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane (DOI): From an Obscure to Pivotal Member of the DOX Family of Serotonergic Psychedelic Agents - A Review". ACS Pharmacol Transl Sci. 7 (6): 1722–1745. doi:10.1021/acsptsci.4c00157. PMC 11184610. PMID 38898956.
  4. ^ a b c Canal CE, Morgan D (2012). "Head-twitch response in rodents induced by the hallucinogen 2,5-dimethoxy-4-iodoamphetamine: a comprehensive history, a re-evaluation of mechanisms, and its utility as a model". Drug Test Anal. 4 (7–8): 556–576. doi:10.1002/dta.1333. PMC 3722587. PMID 22517680.
  5. ^ Shulgin, A, Shulgin, A (1990). "#67 DOI". PiHKAL: A Chemical Love Story. Transform Press. ISBN 978-0963009609. Archived from the original on 2014-10-27. Retrieved 2014-12-17.
  6. ^ "LSD Blotter Acid Mimics (Actually containing 4-IODO-2,5-DIMETHOXYAMPHETAMINE (DOI) and 4-CHLORO-2,5-DIMETHOXYAMPHETAMINE (DOC)) in Lantana, Florida". DEA Microgram Bulletin. Washington, DC: Office of Forensic Sciences, Drug Enforcement Administration. June 2008. Archived from the original on 2009-02-04. Retrieved 12 February 2009.
  7. ^ Nichols DE (2016). "Psychedelics" (PDF). Pharmacological Reviews. 68 (2): 264–355. doi:10.1124/pr.115.011478. ISSN 0031-6997. PMC 4813425. PMID 26841800. Although studies have appeared that employed psilocybin or LSD or a select few other agents, probably the majority of animal experiments have used the "psychedelic" 5-HT2A agonist DOI. That is another unfortunate consequence of the current drug laws. DOI has never been popular as a recreational drug, nor has any clinical study been carried out to compare its effects with classic drugs such as LSD, mescaline, or psilocybin, and only anecdotal reports of its human psychopharmacology exist (e.g., Shulgin and Shulgin, 1991). Although DOI is quite potent, it likely never became popular as a street drug because of its very prolonged duration of action, so it had never been placed into Schedule I of the Controlled Substances Act (although as of November 2015, there are congressional moves afoot to change that). Therefore, DOI has been commercially available to qualified investigators and did not require a U.S. Drug Enforcement Administration license to work with it.
  8. ^ Psychedelics Today (21 January 2025). "Is the DEA Sabotaging Psychedelic Research? Inside the Push to Schedule DOI and DOC". Psychedelics Today. Retrieved 6 June 2025.
  9. ^ Baggott MJ (1 October 2023). "Learning about STP: A Forgotten Psychedelic from the Summer of Love" (PDF). History of Pharmacy and Pharmaceuticals. 65 (1): 93–116. doi:10.3368/hopp.65.1.93. ISSN 2694-3034. Retrieved 27 January 2025.
  10. ^ Trout K, Daley PF (December 2024). "The origin of 2,5-dimethoxy-4-methylamphetamine (DOM, STP)" (PDF). Drug Test Anal. 16 (12): 1496–1508. doi:10.1002/dta.3667. PMID 38419183.
  11. ^ Cite error: The named reference USDOJ was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Federal Register 2023 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference Jane2024 was invoked but never defined (see the help page).
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