ethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate

• ChemBase ID: 70184
• Molecular Formular: C14H16N2O2
• Molecular Mass: 244.28904
• Monoisotopic Mass: 244.12117776
• SMILES: c1ncc(n1[C@H](C)c1ccccc1)C(=O)OCC
• Canonical SMILES: CCOC(=O)c1cncn1[C@@H](c1ccccc1)C
• InChI: InChI=1S/C14H16N2O2/c1-3-18-14(17)13-9-15-10-16(13)11(2)12-7-5-4-6-8-12/h4-11H,3H2,1-2H3/t11-/m1/s1
• InChIKey: NPUKDXXFDDZOKR-LLVKDONJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate
• IUPAC Traditional name: (+)-etomidate; ethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate
• Synonyms: Etomidate; Amidate; R16659; Etomidate; 1-[(1R)-1-Phenylethyl]-1H-imidazole-5-carboxylic Acid Ethyl Ester; Hypnomidate; R-16659; 1-(1-Phenylethyl)-5-ethoxycarbonylimidazole; Etomidate; D-isomer

Database IDs

• CAS Number: 33125-97-2
• EC Number: 251-385-9
• MDL Number: MFCD00869295
• PubChem SID: 162035908; 24894630
• PubChem CID: 667484

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.4663537
• LogD (pH = 7.4): 2.4993365
• Log P: 2.4997861
• Molar Refractivity: 69.5923 cm^3
• Polarizability: 26.606922 Å^3
• Polar Surface Area: 44.12 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; DMSO: >10 mg/mL; Ethanol; Methanol; Water
• Apperance: white powder; White Solid
• Melting Point: 72-74°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: NI4021500
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• TSCA Listed: false
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H400
• GHS Precautionary statements: P273
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... GABRA1(2554)
• Mechanism of Action: Binds at a distinct binding site associated with a Cl- ionopore at the GABA(A) receptor, increasing the duration of time for which the Cl- ionopore is open.; The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.

Product Information

• Purity: >98% (HPLC); 95+%
• Application(s): Short acting intravenous anaesthetic agent used for the induction of general anaesthesia and for sedation for short procedures such as reduction of dislocated joints and cardioversion.
• Empirical Formula (Hill Notation): C14H16N2O2

DETAILS

Sigma Aldrich - E6530

Biochem/physiol Actions
Etomidate is a general anesthetic; potentiates GABAA transmission. The possible neuroprotective effect of etomidate against streptozotocin-induced (STZ-induced) hyperglycaemia were investigated in the rat brain and spinal cord. Etomidate treatment demonstrated neuroprotective effect on the neuronal tissue against the diabetic oxidative damage

Toronto Research Chemicals - E933300

Etomidate is a hypnotic.

REFERENCES

• Goetz, E., et al.: Anaesthesist, 23, 331 (1974)
• Chang, Z. L., et al.: Anal. Profiles Drug Subs., 12, 191 (1974)
• Godefroi, E.F. et al., J. Med. Chem., 1965, 8, 220, (synth)
• Chang, Z.L. et al., Anal. Profiles Drug Subst., 1983, 12, 191, (rev)
• Giese, J.L. et al., Pharmacotherapy (Carlisle, Mass.), 1983, 3, 251, (rev, pharmacol)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 913
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, HOU100