Chemistry:D-Deprenyl

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Short description: Chemical compound

D-Deprenyl
Clinical data
Other namesdextro-N-propargyl-N-methylamphetamine
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC13H17N
Molar mass187.286 g·mol−1
3D model (JSmol)
ChiralityDextrorotatory enantiomer
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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]Selegiline is also a more potent MAO-B inhibitor than D-Deprenyl and is the main motivator for its selection for the medical market.[8]

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 (Ki = 79–1,800 nM) similarly to various other amphetamine derivatives.[9][10][11][12][13] Its l-isomer, selegiline, binds with several-fold lower affinity in comparison.[9]

See also

References

  1. ↑ "The effect of L-deprenyl, D-deprenyl and MDL72974 on mitochondrial respiration: a possible mechanism leading to an adaptive increase in superoxide dismutase activity". Brain Research. Molecular Brain Research 49 (1–2): 127–136. October 1997. doi:10.1016/S0169-328X(97)00135-6. PMID 9387872. 
  2. ↑ "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. January 2013. doi:10.1159/000345043. PMID 23207416. 
  3. ↑ "D-deprenyl protects nigrostriatal neurons against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced dopaminergic neurotoxicity". Synapse 50 (1): 7–13. October 2003. doi:10.1002/syn.10239. PMID 12872288. 
  4. ↑ "(-)-D-Deprenyl attenuates apoptosis in experimental brain ischaemia". European Journal of Pharmacology 430 (2–3): 235–241. November 2001. doi:10.1016/S0014-2999(01)01375-9. PMID 11711036. 
  5. ↑ "Evaluation of the stereoisomers of deprenyl for amphetamine-like discriminative stimulus effects in rats". The Journal of Pharmacology and Experimental Therapeutics 265 (1): 1–6. April 1993. doi:10.1016/S0022-3565(25)38111-5. PMID 8473997. http://jpet.aspetjournals.org/content/265/1/1.abstract. 
  6. ↑ "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): 413–421. January 2006. doi:10.1007/s00213-005-0200-7. PMID 16292593. 
  7. ↑ "Intravenous self-administration studies with l-deprenyl (selegiline) in monkeys". Clinical Pharmacology and Therapeutics 56 (6 Pt 2): 774–780. December 1994. doi:10.1038/clpt.1994.208. PMID 7995020. 
  8. ↑ https://pmc.ncbi.nlm.nih.gov/articles/PMC1360227/
  9. ↑ 9.0 9.1 "Multiple sigma binding sites in the brain". Sigma Receptors. Neuroscience Perspectives. Elsevier Science. 1994. pp. 113–137 (118). ISBN 978-0-12-376350-1. https://books.google.com/books?id=ndRqAAAAMAAJ. 
  10. ↑ "Structure-activity relationships and evolution of sigma receptor ligands (1976-present)". Sigma Receptors. Neuroscience Perspectives. Elsevier Science. 1994. pp. 45–111 (84). ISBN 978-0-12-376350-1. https://books.google.com/books?id=ndRqAAAAMAAJ. 
  11. ↑ "Clorgyline displays high affinity for sigma binding sites in C57BL/6 mouse brain". Eur J Pharmacol 176 (1): 107–108. January 1990. doi:10.1016/0014-2999(90)90139-w. PMID 2155796. 
  12. ↑ "Sigma binding sites in the brain; an emerging concept for multiple sites and their relevance for psychiatric disorders". Life Sci 47 (13): 1073–1081. 1990. doi:10.1016/0024-3205(90)90165-n. PMID 2172677. 
  13. ↑ "Binding of sigma-ligands to C57BL/6 mouse brain membranes: effects of monoamine oxidase inhibitors and subcellular distribution studies suggest the existence of sigma-receptor subtypes". J Pharmacol Exp Ther 257 (1): 141–148. April 1991. doi:10.1016/S0022-3565(25)24697-3. PMID 1850463. 

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