para-Iodoamphetamine
{{Short description|Chemical compound}}
{{DISPLAYTITLE:para-Iodoamphetamine}}
{{Drugbox
| verifiedrevid = 451226630
| IUPAC_name = 1-(4-iodophenyl)propan-2-amine
| image = para-Iodoamphetamine Structure.svg
| image_class = skin-invert-image
| width =
| drug_name = para-Iodoamphetamine
| tradename =
| class = Serotonin releasing agent; Serotonergic neurotoxin
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 21894-72-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = C4UL3HTE7T
| PubChem = 123870
| ChemSpiderID = 110407
| 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).{{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 }}
Pharmacology
=Pharmacodynamics=
PIA acts as a serotonin releasing agent (SRA).{{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 }} In animal drug discrimination tests, PIA fully substitutes for MDMA and (+)-MBDB.
PIA has been described as having either similar serotonergic neurotoxicity as PCA or as having much weaker serotonergic neurotoxicity than PCA.{{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 }}
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-(123I)-para-iodoamphetamine, is a derivative of PIA used as a radiopharmaceutical and diagnostic agent.{{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 = }}
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.
References
{{Reflist}}
{{Monoamine releasing agents}}
{{Monoamine neurotoxins}}
{{Phenethylamines}}
{{DEFAULTSORT:Iodoamphetamine, para-}}
Category:4-Iodophenyl compounds
Category:Monoaminergic neurotoxins