Phenylisobutylamine

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

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 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".

Derivatives

A number of notable derivatives of phenylisobutylamine are known, including the following:

• N-Methyl-α-ethylphenethylamine (MEPEA)
• N,α-Diethylphenethylamine (DEPEA)
• BDB
• MBDB
• EBDB
• 5-MBPB (5-MABB)
• 6-MBPB (6-MABB)
• 4-CAB (α-Et-PCA)
• 4-MAB (α-Et-4-MA)
• Buphedrone
• N-Ethylbuphedrone
• 3F-NEB
• 4-Methylbuphedrone
• Butylone (βk-MBDB)
• Eutylone (βk-EBDB)
• Dibutylone (βk-DMBDB)
• Ariadne (α-Et-DOM)
• 4C-B (α-Et-DOB)
• 4C-T-2 (α-Et-2C-T-2)
• α-Pyrrolidinobutiophenone (α-PBP)
• MPBP
• MDPBP

Additional derivatives with longer α chains also exist, for instance pentedrone, MBDP, pentylone, MDPV, and hexedrone, as well as others, like mexedrone.

Whereas MDMA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA), MBDB appears to be a highly selective serotonin–norepinephrine releasing agent (SNRA) and with significant preference for induction of serotonin release over norepinephrine release.^[4][5][6][7]

The phenylisobutylamine counterparts of psychedelic phenethylamines and amphetamines, for instance MBDB (the α-ethyl homologue of MDMA) and Ariadne (the α-ethyl homologue of DOM), show greatly reduced or abolished psychedelic effects in comparison.^[8][5][9] This has also applied to α-ethyltryptamine (αΕΤ), which is non-hallucinogenic in contrast to α-methyltryptamine (αMT).^[10][4] In the case of Ariadne specifically, it may be due to reduced efficacy in activating the serotonin 5-HT_2A receptor.^[8]

See also

• α-Propylphenethylamine (APPEA)
• 4C (psychedelics)