5-IAI

5-IAI
Systematic (IUPAC) name
	5-iodo-2,3-dihydro-1H-inden-2-amine
Clinical data
Pregnancy cat.	?
Legal status	Uncontrolled
Routes	Oral, Insufflated, Rectal
Identifiers
CAS number	132367-76-1
ATC code	None
PubChem	CID 131506
ChemSpider	116224
UNII	7X16E45Y1X
Chemical data
Formula	C9H10IN
Mol. mass	259.087 g/mol
	SMILES c2c1CC(N)Cc1ccc2I;
	InChI InChI=1S/C9H10IN/c10-8-2-1-6-4-9(11)5-7(6)3-8/h1-3,9H,4-5,11H2 ; Key:BIHPYCDDPGNWQO-UHFFFAOYSA-N ;
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5-Iodo-2-aminoindane (5-IAI) is a drug which acts as a releasing agent of serotonin, norepinephrine, and dopamine.^[1] It was developed in the 1990s by a team led by David E. Nichols at Purdue University.^[2] 5-IAI fully substitutes for MDMA in rodents and is a putative entactogen in humans.^[2] Unlike related aminoindane derivatives like MDAI and MMAI, 5-IAI causes some serotonergic neurotoxicity in rats, but is substantially less toxic than its corresponding amphetamine homologue pIA, with the damage observed barely reaching statistical significance.^[1]

[edit] See also

^ ^a ^b Johnson MP, Conarty PF, Nichols DE (July 1991). "[3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues". European Journal of Pharmacology 200 (1): 9–16. doi:10.1016/0014-2999(91)90659-E. PMID 1685125.
^ ^a ^b Nichols DE, Johnson MP, Oberlender R (January 1991). "5-Iodo-2-aminoindan, a nonneurotoxic analogue of p-iodoamphetamine". Pharmacology, Biochemistry, and Behavior 38 (1): 135–9. doi:10.1016/0091-3057(91)90601-W. PMID 1826785.

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