DOM-AI

DOM-AI
Clinical data
Other names	DOMAI; 4,7-Dimethoxy-5-methyl-2-aminoindane; 2-Amino-4,7-dimethoxy-5-methylindane
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None;
Identifiers
	IUPAC name 4,7-dimethoxy-5-methyl-2,3-dihydro-1H-inden-2-amine;
CAS Number	52904-71-9;
PubChem CID	3016787;
ChemSpider	2284673;
ChEMBL	ChEMBL422189;
CompTox Dashboard (EPA)	DTXSID40967380 ;
Chemical and physical data
Formula	C12H17NO2
Molar mass	207.273 g·mol?1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC(=C2CC(CC2=C1OC)N)OC;
	InChI 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;

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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 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-5, and ZC-B.^[7]^[8]^[2]

References

^ ^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.
^ ^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. Archived from the original (PDF) on August 5, 2023.
^ Nichols DE (August 1981). "Structure-activity relationships of phenethylamine hallucinogens". Journal of Pharmaceutical Sciences. 70 (8): 839–849. Bibcode:1981JPhmS..70..839N. doi:10.1002/jps.2600700802. PMID 7031221.
^ ^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
^ 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.
^ 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.
^ 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.
^ 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.

External links

DOM-AI - Isomer Design

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[Nichols_1974-1] 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.

[Nichols_1978-2] 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. Archived from the original (PDF) on August 5, 2023.

[Nichols_1981-3] Nichols DE (August 1981). "Structure-activity relationships of phenethylamine hallucinogens". Journal of Pharmaceutical Sciences. 70 (8): 839–849. Bibcode:1981JPhmS..70..839N. doi:10.1002/jps.2600700802. PMID 7031221.

[Nichols_1990-4] 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

[Glennon_2002-5] 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.

[Malicky_1974-6] 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.

[Nichols_2018-7] 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.

[Monte_1995-8] 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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