Imiloxan

Imiloxan
Clinical data
ATC code	none;
Identifiers
	IUPAC name (RS)-2-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-1-ethylimidazole;
CAS Number	81167-16-0 ;
PubChem CID	133621;
IUPHAR/BPS	3470;
ChemSpider	117866 ;
UNII	ZJ56PS1DWK;
ChEMBL	ChEMBL578481 ;
CompTox Dashboard (EPA)	DTXSID1045162 ;
Chemical and physical data
Formula	C14H16N2O2
Molar mass	244.289 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN1C=CN=C1CC2COC3=CC=CC=C3O2;
	InChI InChI=1S/C14H16N2O2/c1-2-16-8-7-15-14(16)9-11-10-17-12-5-3-4-6-13(12)18-11/h3-8,11H,2,9-10H2,1H3 ; Key:UXABARREKCJULM-UHFFFAOYSA-N ;
	(what is this?) (verify)

Imiloxan is a drug which is used in scientific research. It acts as a selective antagonist for the α_2B adrenergic receptor,^[1] and has been useful for distinguishing the actions of the different α₂ adrenergic subtypes.^[2]^[3]

Synthesis

The imidazole portion of imiloxan is prepared by the reaction of an imidate with the diethyl acetal of aminoacetaldehyde. N-Alkylation of the imidazole with ethyl iodide gives imiloxan.

References

^ Michel AD, Loury DN, Whiting RL (March 1990). "Assessment of imiloxan as a selective alpha 2B-adrenoceptor antagonist". British Journal of Pharmacology. 99 (3): 560–4. doi:10.1111/j.1476-5381.1990.tb12968.x. PMC 1917331. PMID 1970500.
^ Cobos-Puc LE, Villalón CM, Sánchez-López A, Lozano-Cuenca J, Pertz HH, Görnemann T, Centurión D (January 2007). "Pharmacological evidence that alpha2A- and alpha2C-adrenoceptors mediate the inhibition of cardioaccelerator sympathetic outflow in pithed rats". European Journal of Pharmacology. 554 (2–3): 205–11. doi:10.1016/j.ejphar.2006.09.068. PMID 17109851.
^ Romero TR, de Castro Perez A, de Francischi JN, Gama Duarte ID (April 2009). "Probable involvement of alpha(2C)-adrenoceptor subtype and endogenous opioid peptides in the peripheral antinociceptive effect induced by xylazine". European Journal of Pharmacology. 608 (1–3): 23–7. doi:10.1016/j.ejphar.2009.02.019. PMID 19236861.
^ Caroon, Joan M.; Clark, Robin D.; Kluge, Arthur F.; Olah, Ronald; Repke, David B.; Unger, Stefan H.; Michel, Anton D.; Whiting, Roger L. (1982). "Structure-activity relationships for 2-substituted imidazoles as .alpha.2-adrenoceptor antagonists". Journal of Medicinal Chemistry. 25 (6): 666–70. doi:10.1021/jm00348a012. PMID 6124635.

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[pmid1970500-1] Michel AD, Loury DN, Whiting RL (March 1990). "Assessment of imiloxan as a selective alpha 2B-adrenoceptor antagonist". British Journal of Pharmacology. 99 (3): 560–4. doi:10.1111/j.1476-5381.1990.tb12968.x. PMC 1917331. PMID 1970500.

[pmid17109851-2] Cobos-Puc LE, Villalón CM, Sánchez-López A, Lozano-Cuenca J, Pertz HH, Görnemann T, Centurión D (January 2007). "Pharmacological evidence that alpha2A- and alpha2C-adrenoceptors mediate the inhibition of cardioaccelerator sympathetic outflow in pithed rats". European Journal of Pharmacology. 554 (2–3): 205–11. doi:10.1016/j.ejphar.2006.09.068. PMID 17109851.

[pmid19236861-3] Romero TR, de Castro Perez A, de Francischi JN, Gama Duarte ID (April 2009). "Probable involvement of alpha(2C)-adrenoceptor subtype and endogenous opioid peptides in the peripheral antinociceptive effect induced by xylazine". European Journal of Pharmacology. 608 (1–3): 23–7. doi:10.1016/j.ejphar.2009.02.019. PMID 19236861.

[4] Caroon, Joan M.; Clark, Robin D.; Kluge, Arthur F.; Olah, Ronald; Repke, David B.; Unger, Stefan H.; Michel, Anton D.; Whiting, Roger L. (1982). "Structure-activity relationships for 2-substituted imidazoles as .alpha.2-adrenoceptor antagonists". Journal of Medicinal Chemistry. 25 (6): 666–70. doi:10.1021/jm00348a012. PMID 6124635.

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