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33125-97-2 Usage

Definition

ChEBI: The ethyl ester of 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylic acid. It is an intravenous general anaesthetic with no analgesic activity.

Uses

antiestrogen

General anesthetics

Etomidate is an ultra-short effect non-barbiturate intravenous anesthetic agent allowed to be used in China , it belongs to imidazole derivatives, the appearance is white crystalline powder, melting point 115 ℃, easily soluble in water, methanol, ethanol and propylene glycol, soluble in chloroform, insoluble in acetone, insoluble in ether. Its effects on the central nervous system is similar to barbiturates. Hypnotic effect of Etomidate is strong , and its efficacy is about 12 times higher than thiopental, it has no analgesic effect. It has a rapid onset of anesthesia, after 20 seconds of intravenous injection, it produces anesthesia, anesthesia is maintained for about 5 minutes, it is quick to wake up , increasing the dose will increase the duration of action accordingly. Compared with thiopental ,its anesthesia strength is larger and it has smaller effects on the respiratory and circulatory systems. It is suitable for induction of anesthesia. Intravenous anesthesia, can increase 19% of coronary blood flow and resistance is reduced by 19%. Its obvious advantage is having no negative impact on the cardiovascular system, and it has low toxicity,it has little effect on the respiratory and circulatory system, there is a brief respiratory depression,which makes systolic blood pressure decrease slightly, and make heart rate slightly faster, compared with thiopental, above effects are less, and it has no histamine release effect. It may affect the liver and kidney function and reduce brain oxygen consumption, reduce cerebral blood flow and intracranial pressure. Clinical generally use amount is 0.1~0.4mg/kg, natural wake is 7 to 14 minutes. Distribution half-life is 2.8 minutes, and elimination half-life is 160 minutes. Hydrolyze in the liver and plasma , and the vast majority of metabolites are excreted by the kidneys. The main disadvantages of etomidate is the inhibition of adrenal cortex function, especially after long-term medication.
Induction of anesthesia: quiet, comfortable, heart rate, blood pressure are stable. The usual dose is 0.2~0.3mg/kg. Elderly, frail or critically ill patients can be reduced to 0.1~0.15mg/kg, intravenous drip.It is more suitable for cardiovascular disease, poor cardiac reserve and critically ill patients. Maintenance of intravenous anesthesia or inhalation anesthesia in short surgery or short time heart surgery : intravenous, 0.1~0.2mg/(kg · h). Outpatient minor surgery or special tests: intravenous injection, 0.2~0.3mg/kg.
After the use of the product, there will be clonic muscle contraction, using droperidol or fentanyl before anesthesia can reduce the incidence of myoclonus; if etomidate is used as inducing halothane anesthesia, the amount of halothane should be reduced .
The above information is edited by the chemicalbook of Tian Ye.

Biological Activity

General anesthetic with GABA modulatory and GABA-mimetic actions; selectively interacts with β 2- and β 3-subunit containing GABA A receptors. Short acting and potent hypnotic, with low toxicity.

Chemical Properties

Colourless solid

Brand name

Amidate (Hospira).

Uses

Etomidate is a hypnotic.

Uses

A GABAA receptors agonist.

Uses

Short-time intravenous anesthetics.
InChI:InChI=1/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

33125-97-2 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma (E6530)  Etomidate  >98% (HPLC), powder 33125-97-2 E6530-50MG 6,435.00CNY Detail
Sigma (E6530)  Etomidate  >98% (HPLC), powder 33125-97-2 E6530-10MG 1,531.53CNY Detail
USP (1268750)  Etomidate  United States Pharmacopeia (USP) Reference Standard 33125-97-2 1268750-200MG 4,326.66CNY Detail
Sigma-Aldrich (E2503000)  Etomidate  European Pharmacopoeia (EP) Reference Standard 33125-97-2 E2503000 1,880.19CNY Detail
TCI America (E0897)  Etomidate  >98.0%(GC) 33125-97-2 500mg 2,490.00CNY Detail
TCI America (E0897)  Etomidate  >98.0%(GC) 33125-97-2 100mg 690.00CNY Detail

33125-97-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name etomidate

1.2 Other means of identification

Product number -
Other names (R)-Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:33125-97-2 SDS

33125-97-2Synthetic route

ethanol
64-17-5

ethanol

1-[(1R)-1-phenylethyl]-5-hydroxymethylimidazole

1-[(1R)-1-phenylethyl]-5-hydroxymethylimidazole

etomidate
33125-97-2

etomidate

Conditions
ConditionsYield
With sodium cyanide; manganese(IV) oxide; acetic acid at 80℃; for 12h;85%
(S)-1-phenylethanol
1445-91-6

(S)-1-phenylethanol

1H-imidazole-5-carboxylic acid ethyl ester
23785-21-9

1H-imidazole-5-carboxylic acid ethyl ester

etomidate
33125-97-2

etomidate

Conditions
ConditionsYield
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at -40℃; Mitsunobu reaction; Inert atmosphere;70%
[1-11C]ethyl iodide
97849-55-3

[1-11C]ethyl iodide

(R)-(+)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid
56649-48-0

(R)-(+)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid

etomidate
33125-97-2

etomidate

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydroxide In N,N-dimethyl-formamide at 120℃; for 0.0833333h;
[Ru(2,2′-bipyridine)2(etomidate)2](PF6)2

[Ru(2,2′-bipyridine)2(etomidate)2](PF6)2

water
7732-18-5

water

A

[Ru(2,2′-bipyridine)2(etomidate)(H2O)](PF6)2

[Ru(2,2′-bipyridine)2(etomidate)(H2O)](PF6)2

B

etomidate
33125-97-2

etomidate

Conditions
ConditionsYield
for 0.0166667h; Kinetics; Time; UV-irradiation;
[Ru(2,2′-bipyridine)2(etomidate)2]Cl2

[Ru(2,2′-bipyridine)2(etomidate)2]Cl2

acetonitrile
75-05-8

acetonitrile

A

bis(acetonitrile)bis(2,2'-bipyridine)ruthenium(II) hexafluorophosphate
55124-54-4

bis(acetonitrile)bis(2,2'-bipyridine)ruthenium(II) hexafluorophosphate

B

etomidate
33125-97-2

etomidate

Conditions
ConditionsYield
for 1h; Kinetics; Time; UV-irradiation;
C12H14N2OS

C12H14N2OS

etomidate
33125-97-2

etomidate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; sodium nitrite / tetrahydrofuran; water / 0.5 h / Flow reactor
2: manganese(IV) oxide; sodium cyanide; acetic acid / 12 h / 80 °C
View Scheme
etomidate
33125-97-2

etomidate

(R)-(+)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid
56649-48-0

(R)-(+)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid

Conditions
ConditionsYield
With methanol; lithium hydroxide In tetrahydrofuran; water at 20℃;93%
With sodium hydroxide In methanol at 20℃; for 6h;91.5%
With methanol; sodium hydroxide at 20℃; for 6h;90.1%
isopropyl alcohol
67-63-0

isopropyl alcohol

etomidate
33125-97-2

etomidate

C15H18N2O2
771422-77-6

C15H18N2O2

Conditions
ConditionsYield
With sodium isopropylate at 20℃; for 5h;80%
propan-1-ol
71-23-8

propan-1-ol

etomidate
33125-97-2

etomidate

C15H18N2O2
61045-93-0

C15H18N2O2

Conditions
ConditionsYield
With sodium n-propoxide at 20℃; for 5h;78%
methanol
67-56-1

methanol

etomidate
33125-97-2

etomidate

(R)-Metomidate
61045-91-8

(R)-Metomidate

Conditions
ConditionsYield
With sodium methylate at 20℃; for 5h;71%
etomidate
33125-97-2

etomidate

methylamine
74-89-5

methylamine

A

C13H15N3O
1016274-81-9

C13H15N3O

B

(R)-(-)-[1-phenylethyl]-1H-imidazole
844658-92-0

(R)-(-)-[1-phenylethyl]-1H-imidazole

Conditions
ConditionsYield
In ethanol at 180℃; for 18h; Inert atmosphere; Sealed tube;A 19%
B 65%
potassium hexafluorophosphate
17084-13-8

potassium hexafluorophosphate

trans-[Ru(2,2'-bipyridyl)2(H2O)2](CF3SO3)2

trans-[Ru(2,2'-bipyridyl)2(H2O)2](CF3SO3)2

etomidate
33125-97-2

etomidate

[Ru(2,2′-bipyridine)2(etomidate)2](PF6)2

[Ru(2,2′-bipyridine)2(etomidate)2](PF6)2

Conditions
ConditionsYield
Stage #1: trans-[Ru(2,2'-bipyridyl)2(H2O)2](CF3SO3)2; etomidate In ethanol; water at 85℃; for 24h; Inert atmosphere;
Stage #2: potassium hexafluorophosphate In ethanol; water
47%
etomidate
33125-97-2

etomidate

A

(R)-(+)-ethyl 1-[1-(4-iodophenyl)ethyl]-1H-imidazole-5-carboxylate

(R)-(+)-ethyl 1-[1-(4-iodophenyl)ethyl]-1H-imidazole-5-carboxylate

B

(R)-(+)-ethyl 1-[1-(3-iodophenyl)ethyl]-1H-imidazole-5-carboxylate

(R)-(+)-ethyl 1-[1-(3-iodophenyl)ethyl]-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
With iodine; silver trifluoroacetate; acetic acid In tetrachloromethane at 80℃; for 16h; in the dark;
etomidate
33125-97-2

etomidate

(+)-Azietomidate

(+)-Azietomidate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / 1 h / 100 °C
2: 76 percent / p-(dimethylamino)pyridine; dicyclohexylcarbodiimide / CH2Cl2 / 15 h / 20 °C
View Scheme
etomidate
33125-97-2

etomidate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hydroxide / tetrahydrofuran; methanol / 20 °C
2: phosgene / dichloromethane / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2: oxalyl dichloride / dichloromethane / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / water
2: oxalyl dichloride / dichloromethane
View Scheme
Multi-step reaction with 2 steps
1: lithium hydroxide; methanol / tetrahydrofuran; water / 20 °C
2: oxalyl dichloride / dichloromethane / 1 h / 0 - 20 °C
View Scheme
etomidate
33125-97-2

etomidate

C18H20N2O4
1446482-53-6

C18H20N2O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide / tetrahydrofuran; methanol / 20 °C
2: phosgene / dichloromethane / 0 - 20 °C
3: triethylamine / dichloromethane / 48 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2: oxalyl dichloride / dichloromethane / 0 - 20 °C
3: triethylamine / dichloromethane / 48 h / 0 - 20 °C
View Scheme
etomidate
33125-97-2

etomidate

C19H22N2O4
1446482-57-0

C19H22N2O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide / tetrahydrofuran; methanol / 20 °C
2: phosgene / dichloromethane / 0 - 20 °C
3: dichloromethane; pyridine / 1 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2: oxalyl dichloride / dichloromethane / 0 - 20 °C
3: pyridine / dichloromethane / 1 h / 80 °C
View Scheme
etomidate
33125-97-2

etomidate

C21H26N2O3

C21H26N2O3

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide / tetrahydrofuran; methanol / 20 °C
2: phosgene / dichloromethane / 0 - 20 °C
3: pyridine / dichloromethane / 1 h / 80 °C
View Scheme
etomidate
33125-97-2

etomidate

C18H20N2O4
1446482-69-4

C18H20N2O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide / tetrahydrofuran; methanol / 20 °C
2: phosgene / dichloromethane / 0 - 20 °C
3: triethylamine / dichloromethane / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2: oxalyl dichloride / dichloromethane / 0 - 20 °C
3: triethylamine / dichloromethane / 0 - 20 °C
View Scheme
etomidate
33125-97-2

etomidate

C20H25N3O3*2ClH

C20H25N3O3*2ClH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium hydroxide / tetrahydrofuran; methanol / 20 °C
2.1: phosgene / dichloromethane / 0 - 20 °C
3.1: pyridine / dichloromethane / 2 h / 80 °C
3.2: 1 h / 20 °C
View Scheme
etomidate
33125-97-2

etomidate

C21H27N3O3

C21H27N3O3

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium hydroxide / tetrahydrofuran; methanol / 20 °C
2.1: phosgene / dichloromethane / 0 - 20 °C
3.1: pyridine / dichloromethane / 2 h / 80 °C
3.2: 1 h / 20 °C
4.1: acetonitrile / 0.5 h
4.2: 2 h
View Scheme
etomidate
33125-97-2

etomidate

C20H24N2O4

C20H24N2O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide / tetrahydrofuran; methanol / 20 °C
2: phosgene / dichloromethane / 0 - 20 °C
3: pyridine / dichloromethane / 1 h / 80 °C
View Scheme
etomidate
33125-97-2

etomidate

C20H18N2O4
1446482-52-5

C20H18N2O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide / tetrahydrofuran; methanol / 20 °C
2: phosgene / dichloromethane / 0 - 20 °C
3: triethylamine / dichloromethane / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2: oxalyl dichloride / dichloromethane / 0 - 20 °C
3: triethylamine / dichloromethane / 0 - 20 °C
View Scheme
etomidate
33125-97-2

etomidate

methoxycarbonyl etomidate
1198154-78-7

methoxycarbonyl etomidate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hydroxide / tetrahydrofuran; methanol / 20 °C
2: dmap; dicyclohexyl-carbodiimide / dichloromethane / 48 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 48 h / 20 °C
View Scheme
etomidate
33125-97-2

etomidate

C20H24N2O4

C20H24N2O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2: oxalyl dichloride / dichloromethane / 0 - 20 °C
3: pyridine / dichloromethane / 1 h / 80 °C
View Scheme
etomidate
33125-97-2

etomidate

C24H31N3O6

C24H31N3O6

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2: oxalyl dichloride / dichloromethane / 0 - 20 °C
3: pyridine / dichloromethane / 2 h / 80 °C
View Scheme
etomidate
33125-97-2

etomidate

C19H23N3O4*2ClH

C19H23N3O4*2ClH

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2: oxalyl dichloride / dichloromethane / 0 - 20 °C
3: pyridine / dichloromethane / 2 h / 80 °C
4: hydrogenchloride / ethyl acetate; 1,4-dioxane / 1 h / 20 °C
View Scheme
etomidate
33125-97-2

etomidate

C20H25N3O4

C20H25N3O4

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2.1: oxalyl dichloride / dichloromethane / 0 - 20 °C
3.1: pyridine / dichloromethane / 2 h / 80 °C
4.1: hydrogenchloride / ethyl acetate; 1,4-dioxane / 1 h / 20 °C
5.1: acetonitrile / 0.5 h
5.2: 2 h
View Scheme
etomidate
33125-97-2

etomidate

C20H25N3O4*2ClH

C20H25N3O4*2ClH

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2.1: oxalyl dichloride / dichloromethane / 0 - 20 °C
3.1: pyridine / dichloromethane / 2 h / 80 °C
4.1: hydrogenchloride / ethyl acetate; 1,4-dioxane / 1 h / 20 °C
5.1: acetonitrile / 0.5 h
5.2: 2 h
6.1: hydrogenchloride / ethyl acetate; 1,4-dioxane / 1 h
View Scheme
etomidate
33125-97-2

etomidate

C19H22N2O5

C19H22N2O5

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2: oxalyl dichloride / dichloromethane / 0 - 20 °C
3: pyridine / dichloromethane / 1 h / 80 °C
View Scheme
etomidate
33125-97-2

etomidate

C16H16N2O4
1446482-73-0

C16H16N2O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2: oxalyl dichloride / dichloromethane / 0 - 20 °C
3: triethylamine / dichloromethane / 0 - 20 °C
View Scheme
etomidate
33125-97-2

etomidate

C16H15ClN2O3
1446482-74-1

C16H15ClN2O3

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2: oxalyl dichloride / dichloromethane / 0 - 20 °C
3: triethylamine / dichloromethane / 0 - 20 °C
4: oxalyl dichloride / dichloromethane / 0 - 20 °C
View Scheme
etomidate
33125-97-2

etomidate

C19H20N2O5
1446482-75-2

C19H20N2O5

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: lithium hydroxide; water / methanol; tetrahydrofuran / 20 °C
2: oxalyl dichloride / dichloromethane / 0 - 20 °C
3: triethylamine / dichloromethane / 0 - 20 °C
4: oxalyl dichloride / dichloromethane / 0 - 20 °C
5: triethylamine / dichloromethane / 0 - 20 °C
View Scheme

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