Phenylisobutylamine

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. The dextroisomer of phenylisobutylamine partially substitutes for dextroamphetamine in rats.[1]

Phenylisobutylamine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • 1-phenylbutan-2-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H15N
Molar mass149.237 g·mol−1
3D model (JSmol)
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

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".

See also

References
  1. 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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