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]

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

CAS Number

• 613-89-8

PubChem CID

• 11952

Quick facts Clinical data, Other names ...

2-Aminoacetophenone

Clinical data
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
Identifiers
IUPAC name 2-amino-1-phenylethanone
CAS Number	613-89-8
PubChem CID	11952
ChemSpider	11458
UNII	4M571C83H7
ChEBI	CHEBI:104022
ChEMBL	ChEMBL128079
CompTox Dashboard (EPA)	DTXSID80210206
ECHA InfoCard	100.009.418
Chemical and physical data
Formula	C8H9NO
Molar mass	135.166 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC=C(C=C1)C(=O)CN
InChI InChI=1S/C8H9NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6,9H2 Key:HEQOJEGTZCTHCF-UHFFFAOYSA-N

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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]