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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 to theσ1 receptor (Ki = 79 nM) similarly to various other amphetamine derivatives.[8][9] Itsl-isomer, selegiline, binds with 3.5-fold lower affinity in comparison.[8][9]

See also

[edit]

References

[edit]
  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.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).Sigma Receptors. Academic Press. p. 84.ISBN 978-0-12-376350-1.
  9. ^abStone TW (January 1993).Acetylcholine, Sigma Receptors, CCK and Eicosanoids, Neurotoxins. Taylor & Francis. pp. 124–.ISBN 978-0-7484-0063-8.
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