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.
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| Routes of administration | Oral |
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| Formula | C10H15N |
| Molar mass | 149.237 g·mol−1 |
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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]
"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
editA number of notable derivatives of phenylisobutylamine are known, including the following:
- N,α-Diethylphenethylamine
- 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)
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.[2][3][4][5]
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.[6][3][7] This has also applied to α-ethyltryptamine (αΕΤ), which is non-hallucinogenic in contrast to α-methyltryptamine (αMT).[8][2] In the case of Ariadne specifically, it may be due to reduced efficacy in activating the serotonin 5-HT2A receptor.[6]
References
edit- ^ 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.
- ^ a b Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol. 35 (5): 512–536. doi:10.1177/0269881120920420. PMC 8155739. PMID 32909493.
- ^ a b Aerts LA, Mallaret M, Rigter H (July 2000). "N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine (MBDB): its properties and possible risks". Addict Biol. 5 (3): 269–282. doi:10.1111/j.1369-1600.2000.tb00191.x. PMID 20575841.
- ^ Nichols DE, Marona-Lewicka D, Huang X, Johnson MP (1993). "Novel serotonergic agents" (PDF). Drug Des Discov. 9 (3–4): 299–312. PMID 8400010.
- ^ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
- ^ a b Cunningham MJ, Bock HA, Serrano IC, Bechand B, Vidyadhara DJ, Bonniwell EM, Lankri D, Duggan P, Nazarova AL, Cao AB, Calkins MM, Khirsariya P, Hwu C, Katritch V, Chandra SS, McCorvy JD, Sames D (January 2023). "Pharmacological Mechanism of the Non-hallucinogenic 5-HT2A Agonist Ariadne and Analogs". ACS Chemical Neuroscience. 14 (1): 119–135. doi:10.1021/acschemneuro.2c00597. PMC 10147382. PMID 36521179.
- ^ Clark MR, Shaw HE, Fantegrossi WE (March 2024). Poster 21: In vivo characterization of MBDB and its enantiomers in C57BL/6 and autism-like BTBR T+Itpr3tf/J mice (PDF). 16th Annual Behavior, Biology, and Chemistry: Translational Research in Substance Use Disorders, San Antonio, Texas, Embassy Landmark, 22-24 March 2024.
- ^ Glennon RA, Dukat MG (December 2023). "α-Ethyltryptamine: A Ratiocinatory Review of a Forgotten Antidepressant". ACS Pharmacology & Translational Science. 6 (12): 1780–1789. doi:10.1021/acsptsci.3c00139. PMC 10714429. PMID 38093842.