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Phenylisobutylamine information


Phenylisobutylamine
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • CA: Schedule I
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US: Schedule II (isomer of Methamphetamine)
Identifiers
IUPAC name
  • 1-phenylbutan-2-amine
CAS Number
  • 53309-89-0
PubChem CID
  • 103771
ChemSpider
  • 93687
CompTox Dashboard (EPA)
  • DTXSID50874112 Edit this at Wikidata
Chemical and physical data
FormulaC10H15N
Molar mass149.237 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CCC(CC1=CC=CC=C1)N
InChI
  • InChI=1S/C10H15N/c1-2-10(11)8-9-6-4-3-5-7-9/h3-7,10H,2,8,11H2,1H3
  • Key:IOLQWLOHKZENDW-UHFFFAOYSA-N

Phenylisobutylamine, also known as α-ethylphenethylamine, Butanphenamine, B or AEPEA,[1] is a stimulant drug of the phenethylamine class. It is a higher homologue of amphetamine, differing from amphetamine's molecular structure only by the substitution of the methyl group at the alpha position of the side chain with an ethyl group. Compared to amphetamine, phenylisobutylamine has strongly reduced dopaminergic effects, and instead acts as a selective norepinephrine releasing agent.[citation needed] The dextroisomer of phenylisobutylamine partially substitutes for dextroamphetamine in rats.[1]

A number of derivatives of phenylisobutylamine are known, including BDB, MBDB, EBDB, butylone (βk-MBDB), eutylone (βk-EBDB), Ariadne (α-Et-DOM), 4-CAB, and 4-MAB.

"Phenylisobutylamine" is in fact a chemical misnomer because isobutylamine itself contains a branched chain. The correct name after this style for this class of compound would be "phenylsecbutylamine".

  1. ^ a b Oberlender R, Nichols DE (1991). "Structural variation and (+)-amphetamine-like discriminative stimulus properties". Pharmacol Biochem Behav. 38 (3): 581–586. doi:10.1016/0091-3057(91)90017-V. PMID 2068194. S2CID 19069907.

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