5-IAI

5-IAI
Clinical data
Pregnancy; category	?;
Routes of; administration	Oral, Insufflated, Rectal
ATC code	none
Legal status
Legal status	Uncontrolled;
Identifiers
	IUPAC name 5-iodo-2,3-dihydro-1H-inden-2-amine;
CAS Number	132367-76-1
PubChem (CID)	131506
ChemSpider	116224
UNII	7X16E45Y1X
Chemical and physical data
Formula	C9H10IN
Molar mass	259.087 g/mol
3D model (Jmol)	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 ; 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]

References[edit]

^ ^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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v t e Empathogens/entactogens (category)

Phenylalkyl- amines (other than cathinones)	Unfused benzene ring: 4-CAB 4-FA 4-FMA 4-MTA 4,4'-DMAR Ariadne Metaescaline MMA PMA PMEA PMMA Benzodioxine: EDMA Benzodioxoles: Phenethylamine: { Lophophine } Amphetamines: { 2-Methyl-MDA 2,3-MDA 3,4-MDA 5-Methyl-MDA 6-Methyl-MDA DiFMDA DMMDA DMMDA-2 EIDA MDEA MDMA MDMOH MDOH MMDA MMDA-2 MMDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans and dihidrobenzofurans: 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 5-MBPB 6-APB 6-APDB 6-EAPB 6-MAPB 6-MAPDB Indanes: 5-APDI 5-MAPDI Indole: 6-API Naphtalenes: Methamnetamine Naphthylaminopropane Tetralin: 6-APT

Cyclized phenyl- alkylamines	Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT

Cathinones	3-MMC 4-EMC Brephedrone Butylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone Pentylone

Tryptamines	4-Methyl-αET αET αMT

Chemical classes	Substituted amphetamine Sub. benzofuran Sub. cathinone Sub. MDPEA Sub. PEA Sub. tryptamine

Clinical data

Pregnancy category	?
Routes of administration	Oral, Insufflated, Rectal
ATC code	none
Legal status
Legal status	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^Y
Chemical and physical data
Formula	C₉H₁₀IN
Molar mass	259.087 g/mol
3D model (Jmol)	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
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