Phenylisobutylamine
Stimulant drug of the phenethylamine class
From Wikipedia, the free encyclopedia
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.
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| Other names | α-Ethylphenethylamine; α-Ethylphenylethylamine; Butanphenamine; B; AEPEA |
| Routes of administration | Oral |
| Drug class | Norepinephrineâdopamine releasing agent; Stimulant |
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| Formula | C10H15N |
| Molar mass | 149.237 g·molâ1 |
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Phenylisobutylamine acts as a norepinephrineâdopamine 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:
- α-Ethylmescaline (AEM)
- 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 serotoninânorepinephrineâdopamine releasing agent (SNDRA), MBDB appears to be a highly selective serotoninânorepinephrine 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 (αÎΤ), 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-HT2A receptor.[8]