DOM-AI

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]

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

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]