Fenmetozole

Fenmetozole
Clinical data
ATC code	None;
Identifiers
	IUPAC name 2-[(3,4-dichlorophenoxy)methyl]-4,5-dihydro-1H-imidazole;
CAS Number	41473-09-0 ; 23712-05-2 (HCl);
PubChem CID	32049;
ChemSpider	29721;
UNII	C15WFN6GMO;
ChEMBL	ChEMBL50472;
CompTox Dashboard (EPA)	DTXSID40194371 ;
Chemical and physical data
Formula	C10H10Cl2N2O
Molar mass	245.10 g·mol−1
3D model (JSmol)	Interactive image;
	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

^ Dictionary of organic compounds. London: Chapman & Hall. 1996. ISBN 0-412-54090-8.
^ ^a ^b David J. Triggle (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[isbn0-412-54090-8-1] Dictionary of organic compounds. London: Chapman & Hall. 1996. ISBN 0-412-54090-8.

[isbn0-412-46630-9-2] David J. Triggle (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9.

[pmid1095283-3] 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.

[pmid357069-4] 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.

[pmid6256788-5] 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.

[pmid6792942-6] 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.

[pmid6803283-7] 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.

[pmid2875186-8] 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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Fenmetozole

References

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