D-Deprenyl

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).

Other namesdextro-N-propargyl-N-methylamphetamine

CAS Number

• 4528-51-2 ^Y

PubChem CID

• 199605

ChemSpider

• 172774 ^N

Quick facts Clinical data, Other names ...

D-Deprenyl

Clinical data
Other names	dextro-N-propargyl-N-methylamphetamine
Identifiers
IUPAC name (2S)-N-methyl-1-phenyl-N-prop-2-ynyl-propan-2-amine
CAS Number	4528-51-2 Y
PubChem CID	199605
ChemSpider	172774 N
UNII	YK7HY2RY1W
CompTox Dashboard (EPA)	DTXSID901317215
Chemical and physical data
Formula	C13H17N
Molar mass	187.286 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Dextrorotatory enantiomer
SMILES C#CCN([C@H](Cc1ccccc1)C)C
InChI 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
NY (what is this?)  (verify)

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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 sigma receptors (K_i = 79–1,800 nM) similarly to various other amphetamine derivatives.^{[8][9][10][11][12]} Its l-isomer, selegiline, binds with several-fold lower affinity in comparison.^[8]