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metomidate

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metomidate Basic information

Product Name:
metomidate
Synonyms:
  • metomidate
  • 1-(1-Phenylethyl)-1H-imidazole-5-carboxylic acid methyl ester
  • Methomidate
  • 3-(1-phenylethyl)imidazole-4-carboxylic acid methyl ester
  • methyl 3-(1-phenylethyl)imidazole-4-carboxylate
  • Methyl 3-(1-phenylethyl)imidazole-5-carboxylate
  • 1-(α-Methylbenzyl)iMidazole-5-carboxylic Acid Methyl Ester
  • AquacalM
CAS:
5377-20-8
MF:
C13H14N2O2
MW:
230.26
EINECS:
2263684
Product Categories:
  • Aromatics
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
5377-20-8.mol
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metomidate Chemical Properties

Boiling point:
372.26°C (rough estimate)
Density 
1.13
refractive index 
1.6450 (estimate)
storage temp. 
Refrigerator
solubility 
Chloroform, Methanol
pka
4.15±0.23(Predicted)
color 
Colourless to Pale Yellow
InChI
InChI=1S/C13H14N2O2/c1-10(11-6-4-3-5-7-11)15-9-14-8-12(15)13(16)17-2/h3-10H,1-2H3
InChIKey
FHFZEKYDSVTYLL-UHFFFAOYSA-N
SMILES
C1N(C(C2=CC=CC=C2)C)C(C(OC)=O)=CN=1
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metomidate Usage And Synthesis

Chemical Properties

Colourless Hazy Oil

Uses

Metomidate is a the methyl ester analogue of Etomidate (E933300), with sedative and hypnotic properties. Metomidate is mainly used as an anesthetic for veterinary use on its own or in combination with Azaperone (A802200) and other sedatives.

Definition

ChEBI: Methomidate is a member of imidazoles.

Biological Functions

Metomidate, a methyl analog of the anesthetic agent etomidate, is a potent inhibitor of CYP11B1 (11β-hydroxylase) and CYP11B2 (aldosterone synthase), the final two enzymes involved in cortisol and aldosterone synthesis, respectively.

Mechanism of action

Metomidate reduces plasma cortisol and glucose concentrations and increases fish pigmentation, presumably because of increased production of melanocyte-stimulating hormone on the same primary protein as adrenocorticotropic hormone (ACTH). Imidazole anesthetics (e.g., metomidate and etomidate) interrupt cortisol synthesis in mammals by suppressing the enzyme 11-beta-hydroxylase, which is necessary for cortisol production.

Clinical Use

Metomidate can be 11CH3 labeled and used as a positron emission tomography (PET) radiotracer in combination with high-resolution computed tomography (CT) to detect adrenocortical tumors expressing these enzymes. 

metomidate Supplier

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