Oxethazaine - CAS 126-27-2
Catalog number:
126-27-2
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C28H41N3O3
Molecular Weight:
467.65
COA:
Inquire
Targets:
Others
Description:
Oxethazaine, an effective topical anesthetic, could be used to relieve the pain caused by peptic ulcer disease and esophagitis.
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Purity:
98%
Appearance:
White powder.
Synonyms:
OXETHAZAINE;OXETHAZINE;OXETACAINE;2,2’-((2-hydroxyethyl)imino)bis(n-(1,1-dimethyl-2-phenylethyl)-n-methylaceta;2,2’-((2-hydroxyethyl)imino)bis(n-(alpha,alpha-dimethylphenethyl)-n-acetamid;2,2’-((2-hydroxyethyl)imino)bis(n-(alpha,alpha-dimethylphenethyl)-
Solubility:
Chloroform (Slightly), Methanol (Slightly)
Storage:
-20ºC Freeze
MSDS:
Inquire
Application:
Oxethazaine is an effective topical anesthetic that could be used to relieve the pain caused by peptic ulcer disease and esophagitis.
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity:
Grams-Kilos
Density:
1.093 g/cm3
InChIKey:
FTLDJPRFCGDUFH-UHFFFAOYSA-N
InChI:
InChI=1S/C28H41N3O3/c1-27(2,19-23-13-9-7-10-14-23)29(5)25(33)21-31(17-18-32)22-26(34)30(6)28(3,4)20-24-15-11-8-12-16-24/h7-16,32H,17-22H2,1-6H3
Canonical SMILES:
CC(C)(CC1=CC=CC=C1)N(C)C(=O)CN(CCO)CC(=O)N(C)C(C)(C)CC2=CC=CC=C2
1.Confirming urinary excretion of mephentermine and phentermine following the ingestion of oxethazaine by gas chromatography-mass spectrometry analysis.
Huang WH1, Liu CH, Liu RH, Tseng YL. J Anal Toxicol. 2010 Mar;34(2):73-7.
Mephentermine and phentermine, substances prohibited in sports by the World Anti-Doping Agency, were found for the first time in urine specimens following the administration of a therapeutic medication, oxethazaine. In a recent sporting event, a urine specimen donor who tested positive for mephentermine and phentermine claimed consumption of Mucaine((R)) for treating stomach pain was the reason for testing positive. Five volunteers were administrated oxethazaine (a topical anesthetic found in the multi-ingredient medication Mucaine and its generic equivalent, Stoin, both of which are available in Taiwan), mephentermine, and phentermine. Excretion profiles of mephentermine and phentermine following the administration of these drugs were found to be similar. However, the mephentermine/phentermine ratios found in urine specimens collected at different time points following the administration of oxethazine and mephentermine were found to be characteristically different.
2.Mechanisms involved in the contraction of intrahepatic portal vein branches by clomipramine and oxethazaine in isolated perfused rat livers.
Masuda Y1, Edo T. J Pharmacol Sci. 2005 Jun;98(2):181-4. Epub 2005 Jun 8.
Clomipramine (CLM) and oxethazaine (OXZ) were previously reported to increase portal pressure by contracting portal vein branches (PVBs) in isolated perfused rat liver. In the present study, to characterize the contractile mechanisms, the effects of Y27632, HA1077, staurosporine, papaverine, SKF96365, and sulindac sulfide on the portal pressure increase induced by CLM and OXZ were examined comparatively with those induced by endothelin-1. The results suggest that 1) intrahepatic PVBs employ a Rho-kinase-dependent pathway for sustained contraction, 2) CLM contracts PVBs by activating a Rho-kinase pathway and Ca(2+)-channels, and 3) OXZ acts primarily by promoting Ca(2+) entry through its ionophore-like action.
3.Intrahepatic flow disturbance: possibility of a hidden cause of drug toxicity.
Masuda Y1. J Pharmacol Sci. 2006 Mar;100(3):167-74. Epub 2006 Mar 4.
The liver has an intricate microvascular system that allows homogenous perfusion throughout the organ. However, the regulatory mechanisms of intrahepatic circulation are still unclear, and the effects of drugs on this system have rarely been reported. Oxethazaine, a topical anesthetic, was incidentally found to induce a consistent increase in portal pressure in the isolated perfused rat liver, which led us to characterize this phenomenon. For this, a vital staining method was developed to detect microcirculatory alterations in the isolated liver. Using this method, not only vasoconstrictors like endothelin-1, but the drugs oxethazaine and clomipramine, a tricyclic antidepressant, were found to induce flow redistribution to the deeper and hilar portions of the liver with minimal perfusion at the periphery, which was due to a short-circuit flow at the center owing to the constriction of the intrahepatic portal vein branches. Hepatic nerve stimulation also produced a similar flow disturbance.
4.Biphasic effects of oxethazaine, a topical anesthetic, on the intracellular Ca(2+) concentration of PC12 cells.
Masuda Y1, Oguma T, Kimura A. Biochem Pharmacol. 2002 Aug 15;64(4):677-87.
There have been few reports on the mechanism(s) of action of oxethazaine (OXZ) despite its potent local anesthetic action. Generally, local anesthetics (LAs) not only inhibit Na(+) channels but also affect various membrane functions. In the present study, using PC12 cells as a nerve cell model, the effects of OXZ on intracellular Ca(2+) concentration ([Ca(2+)](i)) were examined in relation to cytotoxicity and dopamine release. [Ca(2+)](i) was determined by the quin2 method. In resting cells, (6-10)x10(-5)M OXZ produced lactate dehydrogenase leakage, which was Ca(2+)-dependent, inhibited by metal Ca(2+) channel blockers, and preceded by a marked increase in [Ca(2+)](i). Some other LAs showed no cytotoxicity at these concentrations. In K(+)-depolarized cells, however, lower concentrations of OXZ (10(-6)-10(-7)M), that had no effect on resting [Ca(2+)](i), inhibited both the dopamine release and the increase of [Ca(2+)](i) in parallel. The inhibitory potency against the [Ca(2+)](i) increase was in the order of nifedipine>OXZ approximately verapamil>diltiazem, and OXZ acted additively on the Ca(2+) channel blockers.
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CAS 126-27-2 Oxethazaine

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