para-Iodomethamphetamine
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| Other names | PIMA; 4-Iodo-N-methylamphetamine; 4-IMA; D-9 |
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| Formula | C10H14IN |
| Molar mass | 275.133 g·mol−1 |
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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
[edit]- Substituted amphetamine
- para-Iodoamphetamine
- para-Bromoamphetamine
- para-Bromomethamphetamine
- para-Chloroamphetamine
- para-Chloromethamphetamine
- para-Fluoroamphetamine
- para-Fluoromethamphetamine
- N-Methyl-DOI
References
[edit]- ^ 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.
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.
- ^ 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
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