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DOM-AI
Clinical data
Other namesDOMAI; 4,7-Dimethoxy-5-methyl-2-aminoindane; 2-Amino-4,7-dimethoxy-5-methylindane
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 4,7-dimethoxy-5-methyl-2,3-dihydro-1H-inden-2-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H17NO2
Molar mass207.273 g·mol−1
3D model (JSmol)
  • CC1=CC(=C2CC(CC2=C1OC)N)OC
  • InChI=1S/C12H17NO2/c1-7-4-11(14-2)9-5-8(13)6-10(9)12(7)15-3/h4,8H,5-6,13H2,1-3H3
  • Key:LBSOVXNUJAVVNS-UHFFFAOYSA-N

DOM-AI, also known as 4,7-dimethoxy-5-methyl-2-aminoindane, is a putative serotonergic psychedelic of the 2-aminoindane group 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 ED50Tooltip median effective dose 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, and ZC-B.[7][8][2]

References

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  1. ^ a b c Nichols DE, Barfknecht CF, Long JP, Standridge RT, Howell HG, Partyka RA, et al. (February 1974). "Potential psychotomimetics. 2. Rigid analogs of 2,5-dimethoxy-4-methylphenylisopropylamine (DOM, STP)". Journal of Medicinal Chemistry. 17 (2): 161–166. doi:10.1021/jm00248a004. PMID 4809251.
  2. ^ a b c Nichols DE, Weintraub HJ, Pfister WR, Yim GK (1978). "The use of rigid analogues to probe hallucinogen receptors" (PDF). NIDA Research Monograph (22): 70–83. PMID 101889.
  3. ^ Nichols DE (August 1981). "Structure-activity relationships of phenethylamine hallucinogens". Journal of Pharmaceutical Sciences. 70 (8): 839–849. doi:10.1002/jps.2600700802. PMID 7031221.
  4. ^ a b c d e Nichols DE, Brewster WK, Johnson MP, Oberlender R, Riggs RM (February 1990). "Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA)". Journal of Medicinal Chemistry. 33 (2): 703–710. 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. ^ Glennon RA, Young R, Rangisetty JB (May 2002). "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. doi:10.1016/s0091-3057(01)00768-7. PMID 11900809.
  6. ^ Malicky JL, Coutts RT (1 February 1974). "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. doi:10.1139/v74-061. ISSN 0008-4042.
  7. ^ Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.
  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 – via ProQuest.
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