Para-Iodoamphetamine

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title: "Para-Iodoamphetamine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["4-iodophenyl-compounds", "monoaminergic-neurotoxins", "serotonin-norepinephrine-dopamine-releasing-agents", "serotonin-receptor-modulators", "substituted-amphetamines"] description: "Chemical compound" topic_path: "general/4-iodophenyl-compounds" source: "https://en.wikipedia.org/wiki/Para-Iodoamphetamine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| 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 = | CAS_number = 21894-72-4 | UNII_Ref = | 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).

Pharmacology

Pharmacodynamics

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

It also has very low affinity for certain serotonin receptors, including the serotonin 5-HT1 receptor (Ki = 7,660nM) and the serotonin 5-HT2 receptor (Ki = 43,000nM).

PIA has been described as having either similar serotonergic neurotoxicity as PCA or as having much weaker serotonergic neurotoxicity than PCA.

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-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

References

1. (1993). "Novel serotonergic agents". Drug des Discov.
2. (December 1995). "Psychostimulant-like effects of p-fluoroamphetamine in the rat". European Journal of Pharmacology.
3. (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem.
4. (January 1991). "5-Iodo-2-aminoindan, a nonneurotoxic analogue of p-iodoamphetamine". Pharmacology, Biochemistry, and Behavior.
5. (January 1989). "Iofetamine hydrochloride I 123: a new radiopharmaceutical for cerebral perfusion imaging". DICP.

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