5-IAI

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5-IAI
Clinical data
Pregnancy
category
  • ?
Routes of
administration		Oral, Insufflated, Rectal
ATC code
  • none
Legal status
Legal status
Identifiers
  • 5-iodo-2,3-dihydro-1H-inden-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC9H10IN
Molar mass259.090 g·mol−1
3D model (JSmol)
  • c2c1CC(N)Cc1ccc2I
  • InChI=1S/C9H10IN/c10-8-2-1-6-4-9(11)5-7(6)3-8/h1-3,9H,4-5,11H2 checkY
  • Key:BIHPYCDDPGNWQO-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

5-Iodo-2-aminoindane (5-IAI) is a drug of the 2-aminoindane group which acts as a releasing agent of serotonin, norepinephrine, and dopamine.[2] It was developed in the 1990s by a team led by David E. Nichols at Purdue University.[3] 5-IAI fully substitutes for MDMA in rodents and is a putative entactogen in humans.[3] 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.[2]

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ 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.
  3. ^ 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. S2CID 20485505.