Etilamfetamine

Chemical compound
  • A08AA06 (WHO)
Legal statusLegal status
Pharmacokinetic dataMetabolismHepaticExcretionRenalIdentifiers
  • N-Ethyl-1-phenyl-propan-2-amine
CAS Number
  • 457-87-4 checkY
PubChem CID
  • 9982
ChemSpider
  • 9588 checkY
UNII
  • 022YON1XMX
KEGG
  • D07114 checkY
ChEMBL
  • ChEMBL276443 checkY
CompTox Dashboard (EPA)
  • DTXSID10860359 Edit this at Wikidata
ECHA InfoCard100.230.711 Edit this at WikidataChemical and physical dataFormulaC11H17NMolar mass163.264 g·mol−13D model (JSmol)
  • Interactive image
  • N(C(Cc1ccccc1)C)CC
  • InChI=1S/C11H17N/c1-3-12-10(2)9-11-7-5-4-6-8-11/h4-8,10,12H,3,9H2,1-2H3 checkY
  • Key:YAGBSNMZQKEFCO-UHFFFAOYSA-N checkY
  (verify)

Etilamfetamine (trade names Apetinil and Adiparthrol; also known as N-ethylamphetamine) is a stimulant drug of the phenethylamine and amphetamine chemical classes. It was invented in the early 20th century and was subsequently used as an anorectic or appetite suppressant in the 1950s,[2] but was not as commonly used as other amphetamines such as amphetamine, methamphetamine, and benzphetamine, and was largely discontinued once newer drugs such as phenmetrazine were introduced. It most likely acts primarily as a dopamine releasing agent.[3] Its activity as a norepinephrine or serotonin releasing agent is not known.

Chemistry

The molecular structure of ethylamphetamine is analogous to methamphetamine, with an ethyl group in place of the methyl group.[Note 1] It can also be considered a substituted amphetamine, with an ethyl group on the amphetamine backbone.[Note 2][Note 3]

Recreational use

Ethylamphetamine can be used as a recreational drug and, while its prevalence is less than amphetamine's, it is still encountered as a substance taken for recreational purposes.

Ethylamphetamine produces effects similar to amphetamine and methamphetamine, though it is of weaker potency.[citation needed] At equipotent dosage, ethylamphetamine is subjectively less euphorigenic.[citation needed]

See also

References

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ Junet R (October 1956). "[Ethylamphetamine in the treatment of obesity]". Praxis. 45 (43): 986–8. PMID 13389142.
  3. ^ Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, Partilla JS, Rothman RB, Katz JL (February 2015). "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug and Alcohol Dependence. 147: 1–19. doi:10.1016/j.drugalcdep.2014.12.005. PMC 4297708. PMID 25548026.

Notes

  1. ^ Amphetamine is a substituted phenethylamine with a methyl group at RA position.
  2. ^ The ethyl group of ethylamphetamine is at RN position, hence the name N-ethylamphetamine.
  3. ^ Ethylamphetamine is structurally similar to N-methylamphetamine (methamphetamine), the ethyl group being replaced in methamphetamine with a methyl group.
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See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
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Phenethylamines


Stimulants: Phenylethanolamine

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