2-Aminoacetophenone Explained
| Width: | 185px |
| Class: | Norepinephrine–dopamine releasing agent
- Stimulant
|
| Cas Number: | 613-89-8 |
| Pubchem: | 11952 |
| Chemspiderid: | 11458 |
| Unii: | 4M571C83H7 |
| Chebi: | 104022 |
| Chembl: | 128079 |
| Synonyms: | Phenylacylamine; β-Ketophenethylamine; β-Ketophenylethylamine; β-Oxophenethylamine; β-Oxophenylethylamine; βk-PEA; bk-PEA; 2-Aminoacetophenone; ortho-Aminoacetophenone; o-Aminoacetophenone; α-Desmethylcathinone |
| Iupac Name: | 2-amino-1-phenylethanone |
| C: | 8 |
| H: | 9 |
| N: | 1 |
| O: | 1 |
| Smiles: | C1=CC=C(C=C1)C(=O)CN |
| Stdinchi: | 1S/C8H9NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6,9H2 |
| Stdinchikey: | HEQOJEGTZCTHCF-UHFFFAOYSA-N |
Phenacylamine, also known as β-ketophenethylamine or as 2-aminoacetophenone, is a substituted phenethylamine derivative.[1] It is the phenethylamine homologue of cathinone (β-ketoamphetamine) and hence is a parent compound of a large number of stimulant and entactogen drugs.[2] [3]
Phenacylamine is also active itself; it is a potent monoamine releasing agent of dopamine (= 208nM) in vitro, whereas it was inactive for serotonin (> 10,000nM) and the for norepinephrine was not assessed but the drug induced 96% release of norepinephrine at a concentration of 10,000nM.[4] [5] Hence, phenacylamine acts as a norepinephrine–dopamine releasing agent (NDRA).
See also
Notes and References
- 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 .
- 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 .
- 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 .
