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Clorgiline

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Clorgiline
Clinical data
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 (INN), orclorgyline (BAN), is amonoamine oxidase inhibitor (MAOI) structurally related topargyline which is described as anantidepressant.[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] It has been found to bind with highaffinity to theσ1 receptor (Ki = 3.2 nM)[3][5] and with very high affinity to theI2 imidazoline receptor (Ki = 40 pM).[6]

Unlikeselegiline, clorgiline does not appear to be amonoaminergic activity enhancer (MAE).[7][8][9][10]

Clorgiline is also amultidrug efflux pump inhibitor.[11] Holmeset al., 2012 reverseazole fungicide resistance using clorgiline, showing promise for its use inmultiple fungicide resistance.[11]

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. ^abStone 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. ^Yossef I (1994).Sigma Receptors. Academic Press. p. 84.ISBN 978-0-12-376350-1.
  6. ^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.
  7. ^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.
  8. ^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.
  9. ^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.
  10. ^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.
  11. ^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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