5-IAI

"NRG-5" redirects here. For the compact food biscuit used for disaster relief, see BP-5 Compact Food.

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]

5-IAI

Clinical data
Pregnancy category	?
Routes of administration	Oral, Insufflated, Rectal
ATC code	none
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act In general: uncontrolled
Identifiers
IUPAC name 5-iodo-2,3-dihydro-1H-inden-2-amine
CAS Number	132367-76-1 N
PubChem CID	131506
ChemSpider	116224 Y
UNII	7X16E45Y1X
CompTox Dashboard (EPA)	DTXSID60927643
Chemical and physical data
Formula	C9H10IN
Molar mass	259.090 g·mol−1
3D model (JSmol)	Interactive image
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 Y Key:BIHPYCDDPGNWQO-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Legal status

Sweden's public health agency suggested classifying 5-IAI as a hazardous substance, on September 25, 2019.^[4]

References

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. 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. 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.
4. "Tretton ämnen föreslås klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 25 September 2019. Archived from the original on 31 October 2019. Retrieved 11 November 2019.