D-Deprenyl

d-Deprenyl
Identifiers
IUPAC name
  • (2S)-N-methyl-1-phenyl-N-prop-2-ynyl-propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC13H17N
Molar mass187.286 g·mol−1
3D model (JSmol)
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
 ☒NcheckY (what is this?)  (verify)

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 (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

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:10.1159/000345043. 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" (PDF). Clinical Pharmacology & Therapeutics. 56 (6): 774–780. doi:10.1038/clpt.1994.208. hdl:2027.42/110034. PMID 7995020. S2CID 10021258.
  8. 1 2 Yossef Itzhak (1994). Sigma Receptors. Academic Press. p. 84. ISBN 978-0-12-376350-1.
  9. 1 2 T. W. Stone (January 1993). Acetylcholine, Sigma Receptors, CCK and Eicosanoids, Neurotoxins. Taylor & Francis. pp. 124–. ISBN 978-0-7484-0063-8.


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