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para-Iodomethamphetamine

From Wikipedia, the free encyclopedia

Pharmaceutical compound
para-Iodomethamphetamine
Clinical data
Other namesPIMA; 4-Iodo-N-methylamphetamine; 4-IMA; D-9
ATC code
  • None
Identifiers
  • 1-(4-iodophenyl)-N-methylpropan-2-amine
CAS Number
PubChemCID
ChemSpider
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC10H14IN
Molar mass275.133 g·mol−1
3D model (JSmol)
  • CC(CC1=CC=C(C=C1)I)NC
  • 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 as4-iodo-N-methylamphetamine (4-IMA) or asD-9, is amonoaminergicdrug of theamphetamine family related topara-chloroamphetamine (PCA).[1][2] It is theN-methylanalogue ofpara-iodoamphetamine (PIA).[1][2] The drug is active in producing behavioral effects in animals, includinghallucinogen-like effects.[2] However, it is unclear whether these effects actually represent hallucinogenic reactions.[2] PIMA does not appear to have been assessed, but otherpara-halogenated amphetamines, such as PCA, are known to act asmonoamine releasing agents and asmonoaminergic neurotoxins.[3][4][5][6][7] They have not proved to bepsychedelic in humans.[8] PIMA was studied byJoseph Knoll and colleagues in the 1960s or 1970s.[2]

See also

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References

[edit]
  1. ^abTrachsel 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. ^abcdeBrimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives".Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97. Archived fromthe original on 2025-05-27. Retrieved2025-06-03.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

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Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
(and further-extended)
Catecholamines
(and close relatives)
Cyclized
phenethylamines
Phenylalkylpyrrolidines
2-Benzylpiperidines
(phenidates)
Phenylmorpholines
(phenmetrazines)
Phenyloxazolamines
(aminorexes)
Isoquinolines and
tetrahydroisoquinolines
2-Aminoindanes
2-Aminotetralins
Others / unsorted
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