Fenmetozole

Fenmetozole
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 2-[(3,4-dichlorophenoxy)methyl]-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−1
3D model (JSmol)
SMILES
  • Clc2ccc(OCC/1=N/CCN\1)cc2Cl

Fenmetozole (DH-524) is a drug which was patented as an antidepressant,[1][2] 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.[3][4][5][6][7] It acts as an α2-adrenergic receptor antagonist similarly to other imidazoles like idazoxan.[8] It was never marketed.[2]

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. 1 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.
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