D-Deprenyl

D-Deprenyl

Identifiers
IUPAC name (2S)-N-methyl-1-phenyl-N-prop-2-ynyl-propan-2-amine
CAS Number	4528-51-2
PubChem (CID)	199605
ChemSpider	172774
Chemical and physical data
Formula	C13H17N
Molar mass	187.29 g·mol^−1
3D model (Jmol)	Interactive image
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 Key:MEZLKOACVSPNER-LBPRGKRZSA-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 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 (K_i = 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

• Clorgiline
• Tranylcypromine

References

1. C Thiffault; R Quirion; J Poirier (October 1997). "The effect of l-deprenyl, d-deprenyl and MDL72974 on mitochondrial respiration: a possible mechanism leading to an adaptive increase in superoxide dismutase activity". Molecular Brain Research. 49 (1–2): 127–136. doi:10.1016/S0169-328X(97)00135-6. PMID 9387872.
2. Srinivasan ThyagaRajan; Kelley S. Madden; Gary W. Boehm; Suzanne Y. Stevens; David L. Felten; Denise L. Bellinger (January 2013). "l-Deprenyl Reverses Age-Associated Decline in Splenic Norepinephrine, Interleukin-2 and Interferon-γ Production in Old Female F344 Rats". Neuroimmunomodulation. 20 (2): 72–78. doi:10.1159/00034504. PMC 3695399. PMID 23207416.
3. Dhanasekharan Muralikrishnan; Supriti Samantaray; Kochupurackal P. Mohanakumar (October 2003). "D-deprenyl protects nigrostriatal neurons against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced dopaminergic neurotoxicity". Synapse. 50 (1): 7–13. doi:10.1002/syn.10239. PMID 12872288.
4. László Simon; Géza Szilágyi; Zoltán Bori; Péter Orbay; Zoltán Nagy (November 2001). "(−)-d-Deprenyl attenuates apoptosis in experimental brain ischaemia". European Journal of Pharmacology. 430 (2–3): 235–241. doi:10.1016/S0014-2999(01)01375-9. PMID 11711036.
5. S Yasar; C W Schindler; E B Thorndike; I Szelenyi; S R Goldberg (April 1993). "Evaluation of the stereoisomers of deprenyl for amphetamine-like discriminative stimulus effects in rats.". Journal of Pharmacology and Experimental Therapeutics. 265 (1): 1–6. PMID 8473997.
6. Yasar S; Gaál J; Panlilio LV; et al. (January 2006). "A comparison of drug-seeking behavior maintained by d-amphetamine, l-deprenyl (selegiline) and d-deprenyl under a second-order schedule in squirrel monkeys". Psychopharmacology. 183 (4): 413–21. doi:10.1007/s00213-005-0200-7. PMC 1360227. PMID 16292593.
7. Winger GD, Yasar S, Negus SS, Goldberg SR (December 1994). "Intravenous self-administration studies with l-deprenyl (selegiline) in monkeys". Clinical Pharmacology & Therapeutics. 56 (6): 774–780. doi:10.1038/clpt.1994.208. PMID 7995020.
8. Yossef Itzhak (1994). Sigma Receptors. Academic Press. p. 84. ISBN 978-0-12-376350-1.
9. T. W. Stone (January 1993). Acetylcholine, Sigma Receptors, CCK and Eicosanoids, Neurotoxins. Taylor & Francis. pp. 124–. ISBN 978-0-7484-0063-8.