Para-Iodoamphetamine
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Other names | PIA; 4-Iodoamphetamine; 4-IA |
| Drug class | Serotonin releasing agent; Serotonergic neurotoxin |
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| Formula | C9H12IN |
| Molar mass | 261.106 g·mol−1 |
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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]
It also has very low affinity for certain serotonin receptors, including the serotonin 5-HT1 receptor (Ki = 7,660 nM) and the serotonin 5-HT2 receptor (Ki = 43,000 nM).[3]
PIA has been described as having either similar serotonergic neurotoxicity as PCA[1] or as having much weaker serotonergic neurotoxicity than PCA.[2][4]
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.[5]
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]