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D-Deprenyl

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
D-Deprenyl
Clinical data
Other namesdextro-N-propargyl-N-methylamphetamine
Identifiers
  • (2S)-N-methyl-1-phenyl-N-prop-2-ynyl-propan-2-amine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC13H17N
Molar mass187.286 g·mol−1
3D model (JSmol)
ChiralityDextrorotatoryenantiomer
  • C#CCN([C@H](Cc1ccccc1)C)C
  • 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 ordextro-N-propargyl-N-methylamphetamine, is anMAO-Binhibitor that metabolizes intod-amphetamine andd-methamphetamine and is therefore also anorepinephrine–dopamine releasing agent.[1][2][3][4][5] It is one of the twoenantiomers ofdeprenyl and is the opposite enantiomer ofl-deprenyl (selegiline).

l-Deprenyl, also an MAO-B inhibitor, metabolizes tol-amphetamine andl-methamphetamine, which are bothnorepinephrine releasing agents. In contrast,d-deprenyl additionally hasdopaminergic effects and has been found to bereinforcing in scientific research, whereasl-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 highaffinity tosigma receptors (Ki = 79–1,800 nM) similarly to various other amphetamine derivatives.[8][9][10][11][12] Itsl-isomer, selegiline, binds with several-fold lower affinity in comparison.[8]

See also

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References

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  1. ^Thiffault C, Quirion R, Poirier J (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".Brain Research. Molecular Brain Research.49 (1–2):127–136.doi:10.1016/S0169-328X(97)00135-6.PMID 9387872.
  2. ^Thyagarajan S, Madden KS, Boehm GW, Stevens SY, Felten DL, Bellinger DL (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. ^Muralikrishnan D, Samantaray S, Mohanakumar KP (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.S2CID 24859873.
  4. ^Simon L, Szilágyi G, Bori Z, Orbay P, Nagy Z (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. ^Yasar S, Schindler CW, Thorndike EB, Szelenyi I, Goldberg SR (April 1993)."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.doi:10.1016/S0022-3565(25)38111-5.PMID 8473997.
  6. ^Yasar S, Gaál J, Panlilio LV, Justinova Z, Molnár SV, Redhi GH, Schindler CW (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):413–421.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 and Therapeutics.56 (6 Pt 2):774–780.doi:10.1038/clpt.1994.208.hdl:2027.42/110034.PMID 7995020.S2CID 10021258.
  8. ^abItzhak Y (1994). "Multiple sigma binding sites in the brain". In Itzhak Y (ed.).Sigma Receptors. Neuroscience Perspectives. Elsevier Science. pp. 113–137 (118).ISBN 978-0-12-376350-1.
  9. ^De Costa BR, He XS (1994). "Structure-activity relationships and evolution of sigma receptor ligands (1976-present)". In Itzhak Y (ed.).Sigma Receptors. Neuroscience Perspectives. Elsevier Science. pp. 45–111 (84).ISBN 978-0-12-376350-1.
  10. ^Itzhak Y, Kassim CO (January 1990). "Clorgyline displays high affinity for sigma binding sites in C57BL/6 mouse brain".Eur J Pharmacol.176 (1):107–108.doi:10.1016/0014-2999(90)90139-w.PMID 2155796.
  11. ^Itzhak Y, Stein I (1990). "Sigma binding sites in the brain; an emerging concept for multiple sites and their relevance for psychiatric disorders".Life Sci.47 (13):1073–1081.doi:10.1016/0024-3205(90)90165-n.PMID 2172677.
  12. ^Itzhak Y, Stein I, Zhang SH, Kassim CO, Cristante D (April 1991). "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.doi:10.1016/S0022-3565(25)24697-3.PMID 1850463.
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