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]