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Clorgiline

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Clorgiline
Clinical data
Other namesClargyline
Drug classMonoamine oxidase inhibitor;MAO-A inhibitor
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • N-[3-(2,4-dichlorophenoxy)propyl]-N-methyl-prop-2-yn-1-amine
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC13H15Cl2NO
Molar mass272.17 g·mol−1
3D model (JSmol)
  • Clc1cc(Cl)ccc1OCCCN(CC#C)C
  • InChI=1S/C13H15Cl2NO/c1-3-7-16(2)8-4-9-17-13-6-5-11(14)10-12(13)15/h1,5-6,10H,4,7-9H2,2H3 checkY
  • Key:BTFHLQRNAMSNLC-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Clorgiline (INNTooltip International Nonproprietary Name), orclorgyline (BANTooltip British Approved Name), is amonoamine oxidase inhibitor (MAOI) and investigationalantidepressant related topargyline.[1][2] Specifically, it is anirreversible andselectiveinhibitor ofmonoamine oxidase A (MAO-A).[3] Clorgiline was never marketed,[1] but it has found use inscientific research.[4]

In addition to its MAOI activity, it has been found to bind with highaffinity to theσ1 receptor (Ki = 3.2–510 nM)[5][6][7][8][9] and with very high affinity to theimidazolineI2 receptor (Ki = 40 pM).[10] Unlikeselegiline, clorgiline does not appear to be amonoaminergic activity enhancer (MAE).[11][12][13][14]

Clorgiline is also amultidrug efflux pump inhibitor.[15] Holmeset al., 2012 reverseazole fungicide resistance using clorgiline, showing promise for its use inmultiple fungicide resistance.[15]

References

[edit]
  1. ^abElks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 304–.ISBN 978-1-4757-2085-3.
  2. ^Morton IK, Hall JM (6 December 2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 80–.ISBN 978-94-011-4439-1.
  3. ^Stone TW (January 1993).Acetylcholine, Sigma Receptors, CCK and Eicosanoids, Neurotoxins. Taylor & Francis. pp. 124–.ISBN 978-0-7484-0063-8.
  4. ^Murphy DL, Karoum F, Pickar D, Cohen RM, Lipper S, Mellow AM, et al. (1998). "Differential trace amine alterations in individuals receiving acetylenic inhibitors of MAO-A (Clorgyline) or MAO-B (Selegiline and pargyline)".MAO — the Mother of all Amine Oxidases. Journal of Neural Transmission. Supplement. Vol. 52. pp. 39–48.doi:10.1007/978-3-7091-6499-0_5.ISBN 978-3-211-83037-6.PMID 9564606.
  5. ^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.
  6. ^De Costa, B. R.; He, X. S. (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.
  7. ^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.
  8. ^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.
  9. ^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.
  10. ^Piletz JE, Halaris A, Ernsberger PR (1994)."Psychopharmacology of imidazoline and alpha 2-adrenergic receptors: implications for depression".Critical Reviews in Neurobiology.9 (1): 29–66 (43).PMID 8828003.
  11. ^Shimazu S, Miklya I (May 2004). "Pharmacological studies with endogenous enhancer substances: β-phenylethylamine, tryptamine, and their synthetic derivatives".Prog Neuropsychopharmacol Biol Psychiatry.28 (3):421–427.doi:10.1016/j.pnpbp.2003.11.016.PMID 15093948.
  12. ^Knoll J (1983)."Deprenyl (selegiline): the history of its development and pharmacological action".Acta Neurol Scand Suppl.95:57–80.doi:10.1111/j.1600-0404.1983.tb01517.x.PMID 6428148.
  13. ^Knoll J (May 1992). "The pharmacological profile of (-)deprenyl (selegiline) and its relevance for humans: a personal view".Pharmacology & Toxicology.70 (5 Pt 1):317–321.doi:10.1111/j.1600-0773.1992.tb00480.x.PMID 1608919.
  14. ^Yen TT, Dalló J, Knoll J (1982). "The aphrodisiac effect of low doses of (-) deprenyl in male rats".Pol J Pharmacol Pharm.34 (5–6):303–308.PMID 6821215.
  15. ^ab
IRTooltip Imidazoline receptor
Non-specific
AAADTooltip Aromatic L-amino acid decarboxylase
MAOTooltip Monoamine oxidase
Phenethylamines
(dopamine,epinephrine,
norepinephrine)
PAHTooltip Phenylalanine hydroxylase
THTooltip Tyrosine hydroxylase
DBHTooltip Dopamine beta-hydroxylase
PNMTTooltip Phenylethanolamine N-methyltransferase
COMTTooltip Catechol-O-methyl transferase
Tryptamines
(serotonin,melatonin)
TPHTooltip Tryptophan hydroxylase
AANATTooltip Serotonin N-acetyl transferase
ASMTTooltip Acetylserotonin O-methyltransferase
Histamine
HDCTooltip Histidine decarboxylase
HNMTTooltip Histamine N-methyltransferase
DAOTooltip Diamine oxidase
σ1
σ2
Unsorted
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