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| Other names | (+/-)-Deprenyl; (±)-Deprenyl; dl-Deprenyl; (±)-Selegiline; (rac)-Selegiline; E-250;N-Propargylmethamphetamine; N,α-Dimethyl-N-2-propynylphenethylamine;N-Propargyl-N-methylamphetamine; Phenylisopropylmethylpropinylamine |
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| Formula | C13H17N |
| Molar mass | 187.286 g·mol−1 |
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Deprenyl, also known by its developmental code nameE-250 and asN-propargylmethamphetamine, is theracemic mixture ofD-deprenyl andL-deprenyl (selegiline).[1][2][3] It was discovered in 1961 inHungary atChinoin Pharmaceutical Company by Zoltan Ecseri andJózsef Knoll, was patented in 1962, and was first described in the literature in 1964 or 1965.[1][2][3]
The drug is amonoamine oxidase inhibitor andnorepinephrine–dopamine releasing agent.[2] It is aprodrug ofmethamphetamine andamphetamine, which mediates the latter action.[4] Deprenyl was studied clinically at high doses of 50 to 100 mg/day and was described as apsychostimulant andantidepressant.[2][1][3] At lower doses,selectiveMAO-B inhibition would be expected, but at these higher doses, dual inhibition ofMAO-A and MAO-B would occur, on the basis ofL-deprenyl.[5]
Subsequent to its synthesis, thestereoisomers of deprenyl were separated.[1] Thedextrorotatory isomer,D-deprenyl, was found to be moretoxic, producing effects likehyperthermia and more potent psychostimulation in rodents.[1][2] Thelevorotatory isomer, selegiline, was much more potent as anMAO-B inhibitor, and was subsequently developed for the treatment ofParkinson's disease anddepression.[2][3]
Deprenyl is reported to result inside effects includingagitation,anxiety, andsleep disturbances more often than selegiline.[6]
Similarly to selegiline, deprenyl is acatecholaminergic activity enhancer (CAE).[7] Bothenantiomers of deprenyl,D-deprenyl and selegiline, are active in this respect, but selegiline is slightly more potent thanD-deprenyl.[7]
Tringer at al. (1971) (76) concluded that deprenyl has a favourable effect in endogenous depression. It was claimed by these authors that the racemic form elicited agitation, anxiety and sleep disturbances more frequently than the (-) isomer.
