D-Deprenyl
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| Other names | dextro-N-propargyl-N-methylamphetamine |
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| Formula | C13H17N |
| Molar mass | 187.286 g·mol−1 |
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| Chirality | Dextrorotatory 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]
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.[8][9][10][11][12] Its l-isomer, selegiline, binds with several-fold lower affinity in comparison.[8]
See also
References
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Yasar S, Gaál J, Panlilio LV, Justinova Z, Molnár SV, Redhi GH, 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): 413–421. doi:10.1007/s00213-005-0200-7. PMC 1360227. PMID 16292593.
- ^ 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.
- ^ a b Itzhak 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.