{{Short description|Chemical compound}} {{DISPLAYTITLE:''para''-Iodoamphetamine}} {{Drugbox | verifiedrevid = 451226630 | drug_name = ''para''-Iodoamphetamine | image = para-Iodoamphetamine.svg | image_class = skin-invert-image | width = 225px
<!--Clinical data--> | tradename = | routes_of_administration = | class = Serotonin releasing agent; Serotonergic neurotoxin
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 21894-72-4 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = C4UL3HTE7T | PubChem = 123870 | ChemSpiderID = 110407 | synonyms = PIA; 4-Iodoamphetamine; 4-IA
<!--Chemical data--> | IUPAC_name = 1-(4-iodophenyl)propan-2-amine | C=9 | H=12 | I=1 | N=1 | SMILES = CC(CC1=CC=C(C=C1)I)N | StdInChI = 1S/C9H12IN/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5,7H,6,11H2,1H3 | StdInChIKey = VZPKOWYCGWOYRF-UHFFFAOYSA-N }}
'''''para''-Iodoamphetamine''' ('''PIA'''), also known as '''4-iodoamphetamine''' ('''4-IA'''), is a monoamine releasing agent (MRA) and serotonergic neurotoxin of the amphetamine family related to ''para''-chloroamphetamine (PCA).<ref name="NicholsMarona-LewickaHuang1993">{{cite journal | vauthors = Nichols DE, Marona-Lewicka D, Huang X, Johnson MP | title = Novel serotonergic agents | journal = Drug des Discov | volume = 9 | issue = 3–4 | pages = 299–312 | date = 1993 | pmid = 8400010 | doi = | url = https://bitnest.netfirms.com/external/DrugDes.Disc/9.299 }}</ref>
==Pharmacology== ===Pharmacodynamics=== PIA acts as a serotonin releasing agent (SRA).<ref name="Marona-LewickaRheeSprague1995">{{cite journal | vauthors = Marona-Lewicka D, Rhee GS, Sprague JE, Nichols DE | title = Psychostimulant-like effects of p-fluoroamphetamine in the rat | journal = European Journal of Pharmacology | volume = 287 | issue = 2 | pages = 105–113 | date = December 1995 | pmid = 8749023 | doi = 10.1016/0014-2999(95)00478-5 }}</ref> In animal drug discrimination tests, PIA fully substitutes for MDMA and (+)-MBDB.<ref name="NicholsMarona-LewickaHuang1993" />
It also has very low affinity for certain serotonin receptors, including the serotonin 5-HT<sub>1</sub> receptor (K<sub>i</sub> = 7,660{{nbsp}}nM) and the serotonin 5-HT<sub>2</sub> receptor (K<sub>i</sub> = 43,000{{nbsp}}nM).<ref name="Glennon1987">{{cite journal | vauthors = Glennon RA | title = Central serotonin receptors as targets for drug research | journal = J Med Chem | volume = 30 | issue = 1 | pages = 1–12 | date = January 1987 | pmid = 3543362 | doi = 10.1021/jm00384a001 | url = | quote = Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites}}</ref>
PIA has been described as having either similar serotonergic neurotoxicity as PCA<ref name="NicholsMarona-LewickaHuang1993" /> or as having much weaker serotonergic neurotoxicity than PCA.<ref name="Marona-LewickaRheeSprague1995" /><ref name="NicholsJohnsonOberlender1991">{{cite journal | vauthors = 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 = 135–139 | date = January 1991 | pmid = 1826785 | doi = 10.1016/0091-3057(91)90601-W | citeseerx = 10.1.1.670.504 | s2cid = 20485505 }}</ref>
==Chemistry== PIA, also known as 4-iodoamphetamine, is a phenethylamine and amphetamine derivative and a ''para''-halogenated amphetamine.
===Analogues=== PIA is closely related to other ''para''-halogenated amphetamines such as PCA, ''para''-bromoamphetamine (PBA), and ''para''-fluoroamphetamine (PFA).
Iofetamine, also known as ''N''-isopropyl-(<sup>123</sup>I)-''para''-iodoamphetamine, is a derivative of PIA used as a radiopharmaceutical and diagnostic agent.<ref name="DruckenbrodWilliamsGelfand1989">{{cite journal | vauthors = Druckenbrod RW, Williams CC, Gelfand MJ | title = Iofetamine hydrochloride I 123: a new radiopharmaceutical for cerebral perfusion imaging | journal = DICP | volume = 23 | issue = 1 | pages = 19–24 | date = January 1989 | pmid = 2655294 | doi = 10.1177/106002808902300103 | url = }}</ref>
5-Iodo-2-aminoindane (5-IAI), the 2-aminoindane analogue of PIA, was an attempt to make a non-neurotoxic analogue of PIA that proved to be less neurotoxic.<ref name="NicholsMarona-LewickaHuang1993" />
==References== {{Reflist}}
{{Monoamine releasing agents}} {{Serotonin receptor modulators}} {{Monoamine neurotoxins}} {{Phenethylamines}}
{{DEFAULTSORT:Iodoamphetamine, para-}}
Category:4-Iodophenyl compounds Category:Monoaminergic neurotoxins Category:Serotonin-norepinephrine-dopamine releasing agents Category:Serotonin receptor modulators Category:Substituted amphetamines