D-Deprenyl

D-Deprenyl
Systematic (IUPAC) name
(2S)-N-methyl-1-phenyl-N-prop-2-ynyl-propan-2-amine
Identifiers
CAS Number 4528-51-2 YesY
PubChem CID 199605
ChemSpider 172774 N
Chemical data
Formula C13H17N
Molar mass 187.29 g·mol−1
 NYesY (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:10.1159/00034504. 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. 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.



This article is issued from Wikipedia - version of the Saturday, April 02, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.