2-Aminoacetophenone

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2-Aminoacetophenone
Clinical data
Other namesPhenylacylamine; 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 classNorepinephrine–dopamine releasing agent; Stimulant
Identifiers
  • 2-amino-1-phenylethanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC8H9NO
Molar mass135.166 g·mol−1
3D model (JSmol)
  • C1=CC=C(C=C1)C(=O)CN
  • InChI=1S/C8H9NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6,9H2
  • Key:HEQOJEGTZCTHCF-UHFFFAOYSA-N

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 (EC50Tooltip half-maximal effective concentration = 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

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References

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