para-Iodoamphetamine

*para*-Iodoamphetamine
Clinical data
Other names	PIA; 4-Iodoamphetamine; 4-IA
Drug class	Serotonin releasing agent; Serotonergic neurotoxin
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 monoamine releasing agent (MRA) and serotonergic neurotoxin of the amphetamine family related to para-chloroamphetamine (PCA).^[1]

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 (K_i = 7,660 nM) and the serotonin 5-HT₂ receptor (K_i = 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]

References

1 2 3 4 Nichols DE, Marona-Lewicka D, Huang X, Johnson MP (1993). "Novel serotonergic agents". Drug des Discov. 9 (3–4): 299–312. PMID 8400010.
1 2 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): 105–113. doi:10.1016/0014-2999(95)00478-5. PMID 8749023.
↑ Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID 3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
↑ Nichols DE, Johnson MP, Oberlender R (January 1991). "5-Iodo-2-aminoindan, a nonneurotoxic analogue of p-iodoamphetamine". Pharmacology, Biochemistry, and Behavior. 38 (1): 135–139. CiteSeerX 10.1.1.670.504. doi:10.1016/0091-3057(91)90601-W. PMID 1826785. S2CID 20485505.
↑ Druckenbrod RW, Williams CC, Gelfand MJ (January 1989). "Iofetamine hydrochloride I 123: a new radiopharmaceutical for cerebral perfusion imaging". DICP. 23 (1): 19–24. doi:10.1177/106002808902300103. PMID 2655294.

[NicholsMarona-LewickaHuang1993-1] 1 2 3 4 Nichols DE, Marona-Lewicka D, Huang X, Johnson MP (1993). "Novel serotonergic agents". Drug des Discov. 9 (3–4): 299–312. PMID 8400010.

[Marona-LewickaRheeSprague1995-2] 1 2 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): 105–113. doi:10.1016/0014-2999(95)00478-5. PMID 8749023.

[Glennon1987-3] Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID 3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites

[NicholsJohnsonOberlender1991-4] Nichols DE, Johnson MP, Oberlender R (January 1991). "5-Iodo-2-aminoindan, a nonneurotoxic analogue of p-iodoamphetamine". Pharmacology, Biochemistry, and Behavior. 38 (1): 135–139. CiteSeerX 10.1.1.670.504. doi:10.1016/0091-3057(91)90601-W. PMID 1826785. S2CID 20485505.

[DruckenbrodWilliamsGelfand1989-5] Druckenbrod RW, Williams CC, Gelfand MJ (January 1989). "Iofetamine hydrochloride I 123: a new radiopharmaceutical for cerebral perfusion imaging". DICP. 23 (1): 19–24. doi:10.1177/106002808902300103. PMID 2655294.

[1]

[2]

[3]

[4]

[5]

v t e Monoaminergic neurotoxins
Dopaminergic	2′-CH₃-MPTP (2′-methyl-MPTP) 2,4,5-THA 2,4,5-THMA 4-MMA 5-S-Cysteinyldopamine 5,6-DHT 6-Hydroxydopa 6-OHDA quinone 6,7-DHT ALDH inhibitors (e.g., disulfiram, methylmercury) Amphetamine V-61 Benomyl Daidzin Dieldrin DOPA quinone DOPAL DOPAL quinone Dopamine Dopamine quinone Fenpropathrin Haloperidol HPP⁺ HPTP Imidazole propionate (ImP) Mancozeb Maneb Mephedrone Methamphetamine Methcathinone Methylone MPP⁺ (cyperquat) MPTP N-Methylnorsalsolinol Norsalsolinol Oxidopamine (6-OHDA) Paraquat Rotenone Salsolinol TaClo (1-TCMTC) Ziram
Noradrenergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4,5-THA 4,5-DHT 5,6-DHT 5,7-DHT 6-Hydroxydopa DOPEGAL DSP-4 MDA (tenamfetamine) Oxidopamine (6-OHDA) Xylamine V-61
Serotonergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4-DCA 2,4,5-THA 2,4,5-THMA pCPE 3-CA 3,4-DCA 4-CAB (α-ethyl-PCA) 4-CMA 4-HO-5-MeO-T 4,5-DHT 5-IAI 5-MAPB 5-MeO-DiPT 5,6-DHT 5,7-DHT 6,7-DHT αET ETAI Fenfluramine Haloperidol HHA (α-methyldopamine) HHMA (α-methylepinine, α,N-dimethyldopamine) HPP⁺ HPTP MBDB MDA (tenamfetamine) MDMA (midomafetamine) Mephedrone Methamphetamine Methylone Norfenfluramine PBA PBMA PCA PCMA PIA TAI
Unsorted	2,5-DDM-DOM 5-HIAL RHPP⁺ RHPTP
See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine metabolism modulators

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Pharmacology

Pharmacodynamics

Chemistry

Analogues

References