2-Aminoacetophenone

Phenethylamine derivative vanc 6 Phenacylamine.svg skin-invert-image 200px Norepinephrine–dopamine releasing agent; Stimulant 613-89-8 11952 11458 4M571C83H7 104022 128079 Phenylacylamine; β-Ketophenethylamine; β-Ketophenylethylamine; β-Oxophenethylamine; β-Oxophenylethylamine; β-Keto-PEA; β-Oxo-PEA; βk-PEA; bk-PEA; 2-Aminoacetophenone; ortho-Aminoacetophenone; o-Aminoacetophenone; α-Desmethylcathinone; α-Demethylcathinone; PAL-27; PAL27 2-amino-1-phenylethanone 8 9 1 1 C1=CC=C(C=C1)C(=O)CN 1S/C8H9NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6,9H2 HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-Aminoacetophenone, also known as β-ketophenethylamine, α-desmethylcathinone, or phenacylamine, is a substituted phenethylamine derivative. Katz DP, Bhattacharya D, Bhattacharya S, Deruiter J, Clark CR, Suppiramaniam V, Dhanasekaran M Synthetic cathinones: "a khat and mouse game" Toxicology Letters 229 2 349–356 September 2014 24973490 10.1016/j.toxlet.2014.06.020 It is the phenethylamine homologue of cathinone (β-ketoamphetamine) and hence is a parent compound of a large number of stimulant and entactogen drugs. Kolesnikova TO, Khatsko SL, Demin KA, Shevyrin VA, Kalueff AV DARK Classics in Chemical Neuroscience: α-Pyrrolidinovalerophenone ("Flakka") ACS Chemical Neuroscience 10 1 168–174 January 2019 30384587 10.1021/acschemneuro.8b00525 German CL, Fleckenstein AE, Hanson GR Bath salts and synthetic cathinones: an emerging designer drug phenomenon Life Sciences 97 1 2–8 February 2014 23911668 3909723 10.1016/j.lfs.2013.07.023 Phenacylamine is also active itself; it is a potent monoamine releasing agent of dopamine (EC50 half-maximal effective concentration = 208nM) in vitro, whereas it was inactive for serotonin (EC50 half-maximal effective concentration > 10,000nM) and the EC50 half-maximal effective concentration for norepinephrine was not assessed but the drug induced 96% release of norepinephrine at a concentration of 10,000nM. Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, Partilla JS, Rothman RB, Katz JL Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter Drug and Alcohol Dependence 147 1–19 February 2015 25548026 4297708 10.1016/j.drugalcdep.2014.12.005 Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB 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 30341459 6475490 10.1007/s00213-018-5063-9 Hence, phenacylamine acts as a norepinephrine–dopamine releasing agent (NDRA). 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. Glennon RA, Young R, Hauck AE, McKenney JD Structure-activity studies on amphetamine analogs using drug discrimination methodology Pharmacol Biochem Behav 21 6 895–901 December 1984 6522418 10.1016/s0091-3057(84)80071-4 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). 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. Glennon RA Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention Adv Pharmacol 69 581–620 2014 24484988 4471862 10.1016/B978-0-12-420118-7.00015-9 See also Substituted cathinone Phenylethanolamine (β-hydroxyphenethylamine) N-Methylphenethylamine β-Keto-N-methylphenethylamine Acetophenone References Category:Beta-Ketophenethylamines Category:Norepinephrine-dopamine releasing agents Category:Stimulants