imiloxan

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 383752803

| IUPAC_name = (RS)-2-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-1-ethylimidazole

| image = Imiloxan.png

| tradename =

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| legal_AU =

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| routes_of_administration =

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| IUPHAR_ligand = 3470

| CAS_number_Ref = {{cascite|correct|??}}

| ATC_prefix = none

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| PubChem = 133621

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = ZJ56PS1DWK

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 578481

| CAS_number = 81167-16-0

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 117866

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = UXABARREKCJULM-UHFFFAOYSA-N

| chemical_formula =

| C=14 | H=16 | N=2 | O=2

| smiles = CCN1C=CN=C1CC2COC3=CC=CC=C3O2

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Imiloxan is a drug which is used in scientific research. It acts as a selective antagonist for the α2B adrenergic receptor,{{cite journal | vauthors = Michel AD, Loury DN, Whiting RL | title = Assessment of imiloxan as a selective alpha 2B-adrenoceptor antagonist | journal = British Journal of Pharmacology | volume = 99 | issue = 3 | pages = 560–4 | date = March 1990 | pmid = 1970500 | pmc = 1917331 | doi = 10.1111/j.1476-5381.1990.tb12968.x }} and has been useful for distinguishing the actions of the different α2 adrenergic subtypes.{{cite journal | vauthors = Cobos-Puc LE, Villalón CM, Sánchez-López A, Lozano-Cuenca J, Pertz HH, Görnemann T, Centurión D | title = Pharmacological evidence that alpha2A- and alpha2C-adrenoceptors mediate the inhibition of cardioaccelerator sympathetic outflow in pithed rats | journal = European Journal of Pharmacology | volume = 554 | issue = 2–3 | pages = 205–11 | date = January 2007 | pmid = 17109851 | doi = 10.1016/j.ejphar.2006.09.068 }}{{cite journal | vauthors = Romero TR, de Castro Perez A, de Francischi JN, Gama Duarte ID | title = Probable involvement of alpha(2C)-adrenoceptor subtype and endogenous opioid peptides in the peripheral antinociceptive effect induced by xylazine | journal = European Journal of Pharmacology | volume = 608 | issue = 1–3 | pages = 23–7 | date = April 2009 | pmid = 19236861 | doi = 10.1016/j.ejphar.2009.02.019 | doi-access = free }}

Synthesis

File:Imiloxan synthesis.svg

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

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