Chemistry: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 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:
- 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 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-HT2A receptor.[8]
See also
- α-Propylphenethylamine (APPEA)
- 4C (psychedelics)
References
- ↑ 1.0 1.1 1.2 "Amphetamine-like Neurochemical and Cardiovascular Effects of α-Ethylphenethylamine Analogs Found in Dietary Supplements". J Pharmacol Exp Ther 376 (1): 118–126. January 2021. doi:10.1124/jpet.120.000129. PMID 33082158.
- ↑ 2.0 2.1 "Reinforcing effects of phenethylamine analogs found in dietary supplements". Psychopharmacology (Berl) 239 (11): 3723–3730. November 2022. doi:10.1007/s00213-022-06246-x. PMID 36190536.
- ↑ 3.0 3.1 "Structural variation and (+)-amphetamine-like discriminative stimulus properties.". Pharmacol Biochem Behav 38 (3): 581–586. 1991. doi:10.1016/0091-3057(91)90017-V. PMID 2068194.
- ↑ 4.0 4.1 "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol 35 (5): 512–536. May 2021. doi:10.1177/0269881120920420. PMID 32909493.
- ↑ 5.0 5.1 "N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine (MBDB): its properties and possible risks". Addict Biol 5 (3): 269–282. July 2000. doi:10.1111/j.1369-1600.2000.tb00191.x. PMID 20575841.
- ↑ "Novel serotonergic agents". Drug Des Discov 9 (3-4): 299–312. 1993. PMID 8400010. https://bitnest.netfirms.com/external/DrugDes.Disc/9.299.
- ↑ "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol 559 (2-3): 132–137. March 2007. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
- ↑ 8.0 8.1 "Pharmacological Mechanism of the Non-hallucinogenic 5-HT2A Agonist Ariadne and Analogs". ACS Chemical Neuroscience 14 (1): 119–135. January 2023. doi:10.1021/acschemneuro.2c00597. PMID 36521179.
- ↑ "Poster 21: In vivo characterization of MBDB and its enantiomers in C57BL/6 and autism-like BTBR T+Itpr3tf/J mice". 16th Annual Behavior, Biology, and Chemistry: Translational Research in Substance Use Disorders, San Antonio, Texas, Embassy Landmark, 22-24 March 2024. March 2024. https://ww2.uthscsa.edu/ARTT/BBC/print/2024Program.pdf#page=21.
- ↑ "α-Ethyltryptamine: A Ratiocinatory Review of a Forgotten Antidepressant". ACS Pharmacology & Translational Science 6 (12): 1780–1789. December 2023. doi:10.1021/acsptsci.3c00139. PMID 38093842.
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