para-Iodoamphetamine

*para*-Iodoamphetamine
Identifiers
	IUPAC name 1-(4-iodophenyl)propan-2-amine;
CAS Number	21894-72-4 ;
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;
	(verify)

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

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 that proved to be less neurotoxic.

^ 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.
^ 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.

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
(verify)