Chemistry:2-Aminoacetophenone
2-Aminoacetophenone, also known as β-ketophenethylamine, α-desmethylcathinone, or phenacylamine, is a substituted phenethylamine derivative.[1][2] It is the phenethylamine homologue of cathinone (β-ketoamphetamine) and hence is a parent compound of a large number of stimulant and entactogen drugs.[1][3][4]
Phenacylamine is also active itself; it is a potent monoamine releasing agent of dopamine (EC50 = 208 nM) in vitro, whereas it was inactive for serotonin (EC50 > 10,000 nM) and the EC50 for norepinephrine was not assessed but the drug induced 96% release of norepinephrine at a concentration of 10,000 nM.[2][5] Hence, phenacylamine acts as a norepinephrine–dopamine releasing agent (NDRA).[2][5]
Despite its activity in vitro however, phenacylamine failed to substitute for dextroamphetamine in animal drug discrimination tests at doses several-fold higher than effective doses of cathinone.[6] It was concluded that, similarly to phenethylamine but in contrast to amphetamine and cathinone, phenylacylamine is likely to be rapidly inactivated via monoamine oxidase (MAO)-mediated metabolism in vivo and will be inactive without concomitant use of a monoamine oxidase inhibitor (MAOI).[6] It has also been suggested that phenacylamine may have diminished blood–brain barrier permeability and limited central activity due to its decreased lipophilicity relative to cathinone.[7]
See also
- Substituted cathinone
- Phenylethanolamine (β-hydroxyphenethylamine)
- N-Methylphenethylamine
- β-Keto-N-methylphenethylamine
- Acetophenone
References
- ↑ 1.0 1.1 "Synthetic cathinones: "a khat and mouse game"". Toxicology Letters 229 (2): 349–356. September 2014. doi:10.1016/j.toxlet.2014.06.020. PMID 24973490.
- ↑ 2.0 2.1 2.2 "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug and Alcohol Dependence 147: 1–19. February 2015. doi:10.1016/j.drugalcdep.2014.12.005. PMID 25548026.
- ↑ "DARK Classics in Chemical Neuroscience: α-Pyrrolidinovalerophenone ("Flakka")". ACS Chemical Neuroscience 10 (1): 168–174. January 2019. doi:10.1021/acschemneuro.8b00525. PMID 30384587.
- ↑ "Bath salts and synthetic cathinones: an emerging designer drug phenomenon". Life Sciences 97 (1): 2–8. February 2014. doi:10.1016/j.lfs.2013.07.023. PMID 23911668.
- ↑ 5.0 5.1 "The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes". Psychopharmacology 236 (3): 915–924. March 2019. doi:10.1007/s00213-018-5063-9. PMID 30341459.
- ↑ 6.0 6.1 "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacol Biochem Behav 21 (6): 895–901. December 1984. doi:10.1016/s0091-3057(84)80071-4. PMID 6522418.
- ↑ "Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention". Adv Pharmacol 69: 581–620. 2014. doi:10.1016/B978-0-12-420118-7.00015-9. PMID 24484988.
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