D-Deprenyl

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d-Deprenyl
Clinical data
Other namesdextro-N-propargyl-N-methylamphetamine
Identifiers
  • (2S)-N-methyl-1-phenyl-N-prop-2-ynyl-propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC13H17N
Molar mass187.286 g·mol−1
3D model (JSmol)
ChiralityDextrorotatory enantiomer
  • C#CCN([C@H](Cc1ccccc1)C)C
  • InChI=1S/C13H17N/c1-4-10-14(3)12(2)11-13-8-6-5-7-9-13/h1,5-9,12H,10-11H2,2-3H3/t12-/m0/s1 ☒N
  • Key:MEZLKOACVSPNER-LBPRGKRZSA-N ☒N
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d-Deprenyl, also known as or dextro-N-propargyl-N-methylamphetamine, is an MAO-B inhibitor that metabolizes into d-amphetamine and d-methamphetamine and is therefore also a norepinephrine–dopamine releasing agent.[1][2][3][4][5] It is one of the two enantiomers of deprenyl and is the opposite enantiomer of l-deprenyl (selegiline).

l-Deprenyl, also an MAO-B inhibitor, metabolizes to l-amphetamine and l-methamphetamine, which are both norepinephrine releasing agents. In contrast, d-deprenyl additionally has dopaminergic effects and has been found to be reinforcing in scientific research, whereas l-deprenyl is not known to have any appreciable psychological reinforcement.[6][7]

In addition to its actions as an MAO-B inhibitor and NDRA, d-deprenyl has been found to bind with high affinity to the σ1 receptor (Ki = 79 nM) similarly to various other amphetamine derivatives.[8][9] Its l-isomer, selegiline, binds with 3.5-fold lower affinity in comparison.[8][9]

See also

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References

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