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| Other names | 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 |
| Drug class | Norepinephrine–dopamine releasing agent;Stimulant |
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| ECHA InfoCard | 100.009.418 |
| Chemical and physical data | |
| Formula | C8H9NO |
| Molar mass | 135.166 g·mol−1 |
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2-Aminoacetophenone, also known asβ-ketophenethylamine,α-desmethylcathinone, orphenacylamine, is asubstituted phenethylaminederivative.[1][2] It is the phenethylamine homologue ofcathinone (β-ketoamphetamine) and hence is a parent compound of a large number ofstimulant andentactogendrugs.[1][3][4]
Phenacylamine is alsoactive itself; it is apotentmonoamine releasing agent ofdopamine (EC50Tooltip half-maximal effective concentration = 208 nM)in vitro, whereas it was inactive forserotonin (EC50 > 10,000 nM) and theEC50 fornorepinephrine was not assessed but the drug induced 96% release of norepinephrine at a concentration of 10,000 nM.[2][5] Hence, phenacylamine acts as anorepinephrine–dopamine releasing agent (NDRA).[2][5]
Despite its activityin vitro however, phenacylamine failed to substitute fordextroamphetamine in animaldrug discrimination tests at doses several-fold higher than effective doses of cathinone.[6] It was concluded that, similarly tophenethylamine but in contrast toamphetamine and cathinone, phenylacylamine is likely to be rapidly inactivated viamonoamine oxidase (MAO)-mediatedmetabolismin vivo and will be inactive without concomitant use of amonoamine oxidase inhibitor (MAOI).[6] It has also been suggested that phenacylamine may have diminishedblood–brain barrierpermeability and limitedcentral activity due to its decreasedlipophilicity relative to cathinone.[7]