Phenylisobutylamine

Phenylisobutylamine
Clinical data
Other names	α-Ethylphenethylamine; α-Ethylphenylethylamine; Butanphenamine; B; AEPEA
Routes of; administration	Oral
Drug class	Norepinephrine–dopamine releasing agent; Stimulant
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 ;
Chemical and physical data
Formula	C10H15N
Molar mass	149.237 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 (AEPEA) or as butanphenamine (B), is a stimulant drug of the phenethylamine and amphetamine families.^[1]^[2]^[3] 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.

Phenylisobutylamine acts as a norepinephrine–dopamine releasing agent (NDRA) and has been found to produce stimulant-like and reinforcing effects in animals.^[1]^[2]^[3] It shows much lower potency and a greater preference for induction of norepinephrine release compared to dextroamphetamine.^[1]

"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".

^ ^a ^b ^c Schindler CW, Thorndike EB, Partilla JS, Rice KC, Baumann MH (January 2021). "Amphetamine-like Neurochemical and Cardiovascular Effects of α-Ethylphenethylamine Analogs Found in Dietary Supplements". J Pharmacol Exp Ther. 376 (1): 118–126. doi:10.1124/jpet.120.000129. PMC 7788351. PMID 33082158.
^ ^a ^b McGriff SA, Chojnacki MR, Thorndike EB, Rice KC, Baumann MH, Schindler CW (November 2022). "Reinforcing effects of phenethylamine analogs found in dietary supplements". Psychopharmacology (Berl). 239 (11): 3723–3730. doi:10.1007/s00213-022-06246-x. PMC 9590234. PMID 36190536.
^ ^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.

[SchindlerThorndikePartilla2021-1] Schindler CW, Thorndike EB, Partilla JS, Rice KC, Baumann MH (January 2021). "Amphetamine-like Neurochemical and Cardiovascular Effects of α-Ethylphenethylamine Analogs Found in Dietary Supplements". J Pharmacol Exp Ther. 376 (1): 118–126. doi:10.1124/jpet.120.000129. PMC 7788351. PMID 33082158.

[McGriffChojnackiThorndike2022-2] McGriff SA, Chojnacki MR, Thorndike EB, Rice KC, Baumann MH, Schindler CW (November 2022). "Reinforcing effects of phenethylamine analogs found in dietary supplements". Psychopharmacology (Berl). 239 (11): 3723–3730. doi:10.1007/s00213-022-06246-x. PMC 9590234. PMID 36190536.

[OberlenderNichols1991-3] 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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