Chemistry:DOM-AI

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DOM-AI, also known as 4,7-dimethoxy-5-methyl-2-aminoindane, is a putative serotonergic psychedelic of the 2-aminoindane family related to DOM.[1][2][3][4] It is a cyclized phenethylamine and the cyclized 2-aminoindane analogue of DOM.[1][2][4]

The drug fully substituted for LSD in rodent drug discrimination tests, suggesting that it may have hallucinogenic effects in humans.[4] However, DOM-AI was much less potent than DOM in these tests, with an ED50 of 2.18 mg/kg, which was approximately 1/15th that of DOM.[4] Nonetheless, DOM-AI is still active in showing psychedelic-like effects in animals, in contrast to its analogues DOM-AT and DOM-CR.[4][5]

DOM-AI was first described in the scientific literature by David E. Nichols and colleagues in 1974.[1][6]

Other cyclized analogues of DOM and related psychedelics besides DOM-AI, DOM-AT, and DOM-CR include DMCPA, TFMBOX, jimscaline, TCB-2, LPH-5, and ZC-B.[7][8][2]

See also

  • Substituted 2-aminoindane

References

  1. ↑ 1.0 1.1 1.2 "Potential psychotomimetics. 2. Rigid analogs of 2,5-dimethoxy-4-methylphenylisopropylamine (DOM, STP)". Journal of Medicinal Chemistry 17 (2): 161–166. February 1974. doi:10.1021/jm00248a004. PMID 4809251. https://bitnest.netfirms.com/external/10.1021/jm00248a004. 
  2. ↑ 2.0 2.1 2.2 "The use of rigid analogues to probe hallucinogen receptors". NIDA Research Monograph (22): 70–83. 1978. PMID 101889. https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=81. 
  3. ↑ "Structure-activity relationships of phenethylamine hallucinogens". Journal of Pharmaceutical Sciences 70 (8): 839–849. August 1981. doi:10.1002/jps.2600700802. PMID 7031221. Bibcode: 1981JPhmS..70..839N. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=f57e387fb5be33822c05b7a3b90888ee717aad21. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 "Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA)". Journal of Medicinal Chemistry 33 (2): 703–710. February 1990. doi:10.1021/jm00164a037. PMID 1967651. "In addition, a 2-aminoindan (5a) and 2-aminotetralin (5b) congener of the hallucinogenic amphetamine [DOM] were also evaluated. [...] Compounds 5a and 5b did not substitute in MDMA-trained rats, although 5a substituted in LSD-trained rats, but with relatively low potency compared to its open-chain counterpart. [...] The results of the drug discrimination studies in rats are presented in Tables I and II. In the LSD-trained rats, stimulus generalization did not occur with any of the compounds 3a,b, 4a,b or 5b. [...] However, indan 5a gave full substitution, with an ED50 = 2.18 mg/kg, approximately 1/15 the potency of the hallucinogen DOM in this assay.24 Earlier studies of this compound, using disruption of a conditioned-avoidance response, did not produce results suggestive of hallucinogenlike activity.18". 
  5. ↑ "Further characterization of the stimulus properties of 5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinoline". Pharmacology, Biochemistry, and Behavior 72 (1–2): 379–387. May 2002. doi:10.1016/s0091-3057(01)00768-7. PMID 11900809. 
  6. ↑ "The Synthesis of Analogs of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM). II. Some Ring-methoxylated 1-Amino-and 2-Aminoindanes". Canadian Journal of Chemistry 52 (3): 381–389. 1 February 1974. doi:10.1139/v74-061. ISSN 0008-4042. 
  7. ↑ Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. 36. 2018. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. https://bitnest.netfirms.com/external/10.1007/7854_2017_475. 
  8. ↑ Monte AP (August 1995). Structure-activity relationships of hallucinogens: Design, synthesis, and pharmacological evaluation of a series of conformationally restricted phenethylamines (Ph.D. thesis). Purdue University. . Retrieved 15 April 2025.

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