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Fenmetozole

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Chemical compound Pharmaceutical compound
Fenmetozole
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 2--4,5-dihydro-1H-imidazole
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H10Cl2N2O
Molar mass245.10 g·mol
3D model (JSmol)
SMILES
  • Clc2ccc(OCC/1=N/CCN\1)cc2Cl

Fenmetozole (DH-524) is a drug which was patented as an antidepressant, but was later studied as an antagonist of the effects of ethanol, though results were poor and it even increased its effects in some cases. It acts as an α2-adrenergic receptor antagonist similarly to other imidazoles like idazoxan. It was never marketed.

Fenoxazoline has the precise same formula, albeit instead of the 3',4'-dich, an ortho-isopropyl group was chosen instead.

References

  1. Dictionary of organic compounds. London: Chapman & Hall. 1996. ISBN 0-412-54090-8.
  2. ^ David J. Triggle (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9.
  3. McNamee HB, Mendelson JH, Korn J (June 1975). "Fenmetozole in acute alcohol intoxication in man". Clinical Pharmacology and Therapeutics. 17 (6): 735–7. doi:10.1002/cpt1975176735. PMID 1095283. S2CID 68796969.
  4. Griffis LC, Bright TP, Cerimele BJ, Forney RB (September 1978). "Combined effects of fenmetozole and ethanol". Clinical Pharmacology and Therapeutics. 24 (3): 350–3. doi:10.1002/cpt1978243350. PMID 357069. S2CID 9289874.
  5. Frye GD, Breese GR, Mailman RB, Vogel RA, Ondrusek MG, Mueller RA (1980). "An evaluation of the selectivity of fenmetozole (DH-524) reversal of ethanol-induced changes in central nervous system function". Psychopharmacology. 69 (2): 149–55. doi:10.1007/BF00427641. PMID 6256788. S2CID 25303633.
  6. Vogel RA, Frye GD, Koepke KM, Mailman RB, Mueller RA, Breese GR (1981). "Differential effects of TRH, amphetamine, naloxone, and fenmetozole on ethanol actions: attenuation of the effects of punishment and impairment of aerial righting reflex". Alcoholism: Clinical and Experimental Research. 5 (3): 386–92. doi:10.1111/j.1530-0277.1981.tb04921.x. PMID 6792942.
  7. Frye GD, Breese GR (1981). "An evaluation of the locomotor stimulating action of ethanol in rats and mice". Psychopharmacology. 75 (4): 372–9. doi:10.1007/BF00435856. PMID 6803283. S2CID 34953445.
  8. Stillings MR, England CD, Welbourn AP, Smith CF (September 1986). "Effect of methoxy substitution on the adrenergic activity of three structurally related alpha 2-adrenoreceptor antagonists". Journal of Medicinal Chemistry. 29 (9): 1780–3. doi:10.1021/jm00159a037. PMID 2875186.
Adrenergic receptor modulators
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
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