para-Iodoamphetamine

para-Iodoamphetamine (PIA), also known as 4-iodoamphetamine (4-IA), is a research chemical of the phenethylamine and amphetamine chemical classes.

para-Iodoamphetamine
Identifiers
IUPAC name
  • 1-(4-iodophenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC9H12IN
Molar mass261.106 g·mol−1
3D model (JSmol)
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
  (verify)

It acts as a selective serotonin releasing agent and is also a MAOI.[1]

PIA is rumored to be a serotonergic neurotoxin on the account of that being reported to be the case for para-chloroamphetamine.

However, PIA is a much weaker 5-HT neurotoxin than is the case for PCA.[2]

Analogs

5-IAI was an attempt to make a non-neurotoxic analog of PIA.

See also

References

  1. 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): 105–13. doi:10.1016/0014-2999(95)00478-5. PMID 8749023.
  2. Nichols DE, Johnson MP, Oberlender R (January 1991). "5-Iodo-2-aminoindan, a nonneurotoxic analogue of p-iodoamphetamine". Pharmacology, Biochemistry, and Behavior. 38 (1): 135–9. CiteSeerX 10.1.1.670.504. doi:10.1016/0091-3057(91)90601-W. PMID 1826785. S2CID 20485505.
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