View source for 5-IAI

{{Drugbox
| IUPAC_name               = 5-iodo-2,3-dihydro-1''H''-inden-2-amine
| image                    = 5-Iodo-2-aminoindane.png
| CAS_number               = 132367-76-1
| ATC_prefix               = none
| ATC_suffix               = 
| PubChem                  = 131506
| ChemSpiderID             = 116224
| C = 9 | H = 10 | I = 1 | N = 1
| molecular_weight         = 259.087 g/mol
| smiles                   = c2c1CC(N)Cc1ccc2I
| bioavailability          = 
| metabolism               = 
| elimination_half-life    = 
| excretion                = 
| pregnancy_category       = ?
| legal_status             = Uncontrolled
| routes_of_administration = [[Mouth|Oral]], [[Insufflated]], [[Rectal]]
}}

'''5-Iodo-2-aminoindane''' ('''5-IAI''') is a [[drug]] which acts as a [[releasing agent]] of [[serotonin]], [[norepinephrine]], and [[dopamine]].<ref name="pmid1685125">{{cite journal | author = Johnson MP, Conarty PF, Nichols DE | title = [3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues | journal = European Journal of Pharmacology | volume = 200 | issue = 1 | pages = 9–16 | year = 1991 | month = July | pmid = 1685125 | doi = | url = }}</ref> It was developed in the 1990s by a team led by [[David E. Nichols]] at [[Purdue University]].<ref name="pmid1826785">{{cite journal | author = Nichols DE, Johnson MP, Oberlender R | title = 5-Iodo-2-aminoindan, a nonneurotoxic analogue of p-iodoamphetamine | journal = Pharmacology, Biochemistry, and Behavior | volume = 38 | issue = 1 | pages = 135–9 | year = 1991 | month = January | pmid = 1826785 | doi = | url = http://linkinghub.elsevier.com/retrieve/pii/0091-3057(91)90601-W}}</ref> 5-IAI fully substitutes for [[3,4-methylenedioxy-N-methylamphetamine|MDMA]] in rodents and is a putative [[entactogen]] in humans.<ref name="pmid1826785" /> Unlike related [[2-aminoindane|aminoindane]] derivatives like [[5,6-methylenedioxy-2-aminoindane|MDAI]] and [[5-methoxy-6-methyl-2-aminoindane|MMAI]], 5-IAI causes some [[serotonergic]] [[neurotoxicity]] in rats, but is substantially less toxic than the its corresponding [[substituted amphetamine|amphetamine]] homologue [[para-iodoamphetamine|pIA]], with the damage observed barely reaching statistical significance.<ref name="pmid1685125" />

== See also ==
* [[2-Aminoindane]] (2-AI)
* [[para-Iodoamphetamine|''para''-Iodoamphetamine]] (pIA)
* [[6-Chloro-2-aminotetralin]] (6-CAT)

== References ==
{{Reflist}}

{{Entactogens}}
{{Stimulants}}
{{Adrenergics}}
{{Dopaminergics}}
{{Serotonergics}}

{{DEFAULTSORT:Iodo-2-aminoindane, 5-}}
[[Category:Amines]]
[[Category:Indanes]]
[[Category:Entactogens and Empathogens]]
[[Category:Monoamine releasing agents]]
[[Category:Stimulants]]
[[Category:2Fix]]