Para-Iodomethamphetamine

*para*-Iodomethamphetamine
Clinical data
Other names	PIMA; 4-Iodo-N-methylamphetamine; 4-IMA; D-9
ATC code	None;
Identifiers
	IUPAC name 1-(4-iodophenyl)-N-methylpropan-2-amine;
CAS Number	4302-90-3;
PubChem CID	107259;
ChemSpider	96528;
CompTox Dashboard (EPA)	DTXSID60962852 ;
Chemical and physical data
Formula	C10H14IN
Molar mass	275.133 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC=C(C=C1)I)NC;
	InChI InChI=1S/C10H14IN/c1-8(12-2)7-9-3-5-10(11)6-4-9/h3-6,8,12H,7H2,1-2H3; Key:MXJYUKFIZBQAJV-UHFFFAOYSA-N;

para-Iodomethamphetamine (PIMA), also known as 4-iodo-N-methylamphetamine (4-IMA) or as D-9, is a monoaminergic drug of the amphetamine family related to para-chloroamphetamine (PCA).^[1]^[2] It is the N-methyl analogue of para-iodoamphetamine (PIA).^[1]^[2] The drug is active in producing behavioral effects in animals, including hallucinogen-like effects.^[2] However, it is unclear whether these effects actually represent hallucinogenic reactions.^[2] PIMA does not appear to have been assessed, but other para-halogenated amphetamines, such as PCA, are known to act as monoamine releasing agents and as monoaminergic neurotoxins.^[3]^[4]^[5]^[6]^[7] They have not proved to be psychedelic in humans.^[8] PIMA was studied by Joseph Knoll and colleagues in the 1960s or 1970s.^[2]

References

^ ^a ^b Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. p. 405. ISBN 978-3-03788-700-4. OCLC 858805226.
^ ^a ^b ^c ^d ^e Brimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97. Archived from the original on 2025-05-27. Retrieved 2025-06-03. Table 3.7.—ACTIVITIES OF SOME HALLUCINOGENIC N-METHYLAMPHETAMINES (data from Knoll, 1970; Knoll and others, 1966) [...] R: 4-I [...]
^ Fuller RW (May 1992). "Effects of p-chloroamphetamine on brain serotonin neurons". Neurochemical Research. 17 (5): 449–456. doi:10.1007/BF00969891. PMID 1528354.
^ Fuller RW (June 1978). "Structure-activity relationships among the halogenated amphetamines". Annals of the New York Academy of Sciences. 305 (1): 147–159. Bibcode:1978NYASA.305..147F. doi:10.1111/j.1749-6632.1978.tb31518.x. PMID 152079.
^ Blough B (July 2008). "Dopamine-releasing agents" (PDF). In Trudell ML, Izenwasser S (eds.). Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. OL 18589888W.
^ Luethi D, Walter M, Zhou X, Rudin D, Krähenbühl S, Liechti ME (2019). "Para-Halogenation Affects Monoamine Transporter Inhibition Properties and Hepatocellular Toxicity of Amphetamines and Methcathinones". Frontiers in Pharmacology. 10: 438. doi:10.3389/fphar.2019.00438. PMC 6491784. PMID 31068823.
^ Fitzgerald LR, Gannon BM, Walther D, Landavazo A, Hiranita T, Blough BE, et al. (March 2024). "Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones". Neuropharmacology. 245: 109827. doi:10.1016/j.neuropharm.2023.109827. PMC 10842458. PMID 38154512.{{cite journal}}: CS1 maint: article number as page number (link)
^ Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6.