Phenacylamine

Phenacylamine
Clinical data
Other names	Phenylacylamine; β-Ketophenethylamine; β-Ketophenylethylamine; β-Oxophenethylamine; β-Oxophenylethylamine; βk-PEA; bk-PEA; 2-Aminoacetophenone; ortho-Aminoacetophenone; o-Aminoacetophenone; α-Desmethylcathinone
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;

Phenacylamine, also known as β-ketophenethylamine or as 2-aminoacetophenone, 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]

^ ^a ^b Katz DP, Bhattacharya D, Bhattacharya S, Deruiter J, Clark CR, Suppiramaniam V, et al. (September 2014). "Synthetic cathinones: "a khat and mouse game"". Toxicology Letters. 229 (2): 349–356. doi:10.1016/j.toxlet.2014.06.020. PMID 24973490.
^ ^a ^b ^c Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, et al. (February 2015). "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug and Alcohol Dependence. 147: 1–19. doi:10.1016/j.drugalcdep.2014.12.005. PMC 4297708. PMID 25548026.
^ Kolesnikova TO, Khatsko SL, Demin KA, Shevyrin VA, Kalueff AV (January 2019). "DARK Classics in Chemical Neuroscience: α-Pyrrolidinovalerophenone ("Flakka")". ACS Chemical Neuroscience. 10 (1): 168–174. doi:10.1021/acschemneuro.8b00525. PMID 30384587.
^ German CL, Fleckenstein AE, Hanson GR (February 2014). "Bath salts and synthetic cathinones: an emerging designer drug phenomenon". Life Sciences. 97 (1): 2–8. doi:10.1016/j.lfs.2013.07.023. PMC 3909723. PMID 23911668.
^ ^a ^b Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, et al. (March 2019). "The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes". Psychopharmacology. 236 (3): 915–924. doi:10.1007/s00213-018-5063-9. PMC 6475490. PMID 30341459.