Para-Iodoamphetamine

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).^[1]

para-Iodoamphetamine

Clinical data
Drug class	Serotonin releasing agent; Serotonergic neurotoxin
Identifiers
IUPAC name 1-(4-iodophenyl)propan-2-amine
CAS Number	21894-72-4 Y
PubChem CID	123870
ChemSpider	110407
UNII	C4UL3HTE7T
CompTox Dashboard (EPA)	DTXSID20897232
Chemical and physical data
Formula	C9H12IN
Molar mass	261.106 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC=C(C=C1)I)N
InChI InChI=1S/C9H12IN/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5,7H,6,11H2,1H3 Key:VZPKOWYCGWOYRF-UHFFFAOYSA-N
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Pharmacology

Pharmacodynamics

PIA acts as a serotonin releasing agent (SRA).^[2] In animal drug discrimination tests, PIA fully substitutes for MDMA and (+)-MBDB.^[1]

PIA has been described as having either similar serotonergic neurotoxicity as PCA^[1] or as having much weaker serotonergic neurotoxicity than PCA.^[2][3]

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.^[4]

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.^[1]

References

1. Nichols DE, Marona-Lewicka D, Huang X, Johnson MP (1993). "Novel serotonergic agents". Drug des Discov. 9 (3–4): 299–312. PMID 8400010.
2. Marona-Lewicka D, Rhee GS, Sprague JE, Nichols DE (December 1995). "Psychostimulant-like effects of p-fluoroamphetamine in the rat". European Journal of Pharmacology. 287 (2): 105–113. doi:10.1016/0014-2999(95)00478-5. PMID 8749023.
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): 135–139. CiteSeerX 10.1.1.670.504. doi:10.1016/0091-3057(91)90601-W. PMID 1826785. S2CID 20485505.
4. Druckenbrod RW, Williams CC, Gelfand MJ (January 1989). "Iofetamine hydrochloride I 123: a new radiopharmaceutical for cerebral perfusion imaging". DICP. 23 (1): 19–24. doi:10.1177/106002808902300103. PMID 2655294.