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
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]

See also

• Substituted amphetamine
• para-Iodoamphetamine
• para-Bromoamphetamine
• para-Bromomethamphetamine
• para-Chloroamphetamine
• para-Chloromethamphetamine
• para-Fluoroamphetamine
• para-Fluoromethamphetamine
• N-Methyl-DOI

References

1. 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.
2. Brimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97. Table 3.7.—ACTIVITIES OF SOME HALLUCINOGENIC N-METHYLAMPHETAMINES (data from Knoll, 1970; Knoll and others, 1966) [...] R: 4-I [...]
3. Fuller RW (May 1992). "Effects of p-chloroamphetamine on brain serotonin neurons". Neurochemical Research. 17 (5): 449–456. doi:10.1007/BF00969891. PMID   1528354.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.

External links

• 4-IMA - Isomer Design