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Droperidol

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Name

Droperidol

EINECS 208-957-8
CAS No. 548-73-2 Density 1.269 g/cm3
PSA 58.10000 LogP 3.61630
Solubility 4.1mg/L(30 oC) Melting Point 148-149 °C
Formula C22H22FN3O2 Boiling Point N/A
Molecular Weight 379.434 Flash Point N/A
Transport Information UN 3249 Appearance Pale yellow solid
Safety 36 Risk Codes 22
Molecular Structure Molecular Structure of 548-73-2 (DROPERIDOL) Hazard Symbols HarmfulXn
Synonyms

2-Benzimidazolinone,1-[1-[3-(p-fluorobenzoyl)propyl]-1,2,3,6-tetrahydro-4-pyridyl]- (8CI);1-(1-[4-(p-Fluorophenyl)-4-oxobutyl]-1,2,3,6-tetrahydro-4-pyridyl)-2-benzimidazolinone;1-[1-[3-(p-Fluorobenzoyl)propyl]-1,2,3,6-tetrahydro-4-pyridyl]-2-benzimidazolinone;Dehydrobenzperidol;Dridol;Droleptan;Inapsin;Inopsin;McN-JR 4749;NSC 169874;Neurolidol;R 4749;Sintodril;1-{1-[4-(4-fluorophenyl)-4-oxobutyl]-1,2,3,6-tetrahydropyridin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one;

Article Data 6

Droperidol Synthetic route

C22H22FN3O2C2H4O

548-73-2

droperidol

Conditions
ConditionsYield
With hydrogenchloride In methanol for 1.5h;300 mg
60373-72-0

1-(p-Fluorophenyl)-4-[4-(2-oxo-1-benzimidazolinyl)-1,2,3,6-tetrahydro-1-pyridyl]-1-butanol

548-73-2

droperidol

Conditions
ConditionsYield
In chloroform

Droperidol History

Droperidol  is discovered at Janssen Pharmaceutica in 1961, droperidol is a butyrophenone, and is a potent D2 (dopamine receptor) antagonist with some histamine and serotonin antagonist activity.
It has a central antiemetic prevents postoperative nausea and vomiting in adults using doses as low as 0.625 mg,and as an intramuscular injection,an antipsychotic in doses ranging from 5 to 10 mg given. When use in intramuscular sedation has been replaced by intramuscular preparations of haloperidol, midazolam, clonazepam and olanzapine.

Droperidol Specification

The Droperidol, with the CAS registry number 548-73-2 and EINECS registry number 208-957-8, has the systematic name of 1-{1-[4-(4-fluorophenyl)-4-oxobutyl]-1,2,3,6-tetrahydropyridin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one. It is a kind of pale yellow solid, and belongs to the following product categories: Heterocyclic Compounds; Intermediates & Fine Chemicals; Pharmaceuticals. The molecular formula of this chemical is C22H22FN3O2. It is harmful if swallowed. Therefore, you had better wear suitable protective clothing while dealing with this chemical. What's more, it should be stored at 2-8 °C.

The physical properties of Droperidol are as following: (1)ACD/LogP: 3.51; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.46; (4)ACD/LogD (pH 7.4): 3.11; (5)ACD/BCF (pH 5.5): 2.44; (6)ACD/BCF (pH 7.4): 108.17; (7)ACD/KOC (pH 5.5): 17.22; (8)ACD/KOC (pH 7.4): 763.15; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 43.86 Å2; (13)Index of Refraction: 1.613; (14)Molar Refractivity: 104.06 cm3; (15)Molar Volume: 298.7 cm3; (16)Polarizability: 41.25×10-24cm3; (17)Surface Tension: 51.3 dyne/cm; (18)Density: 1.269 g/cm3.

Preparation of Droperidol: It can be synthesized from 1-benzyl-3-carbethoxypiperidin-4-one, which is reacted with o-phenylendiamine. Under the reaction conditions, 1,5-benzdiazepine rearranges into 1-(1-benzyl-1,2,3,6-tetrahydro-4-piridyl)-2-benzymidazolone. Debenzylation of the resulting product with hydrogen over catalyst palladium, and subsequent alkylation of this using 4-chloro-4'-fluorobutyrophenone, and the yield is droperidol.

Droperidol can be synthesized from 1-benzyl-3-carbethoxypiperidin-4-one and o-phenylendiamine, and after recomposition, the resluting product reacts with 4-chloro-4'-fluorobutyrophenone, the aim product is obtained

Uses of Droperidol: It is a D1, D2 dopamine receptor antagonist and used as butyrophenone antipsychotic and anti-emetic. It is also used for the treatment of neuroleptanalgesic anesthesia and sedation in intensive-care.

You can still convert the following datas into molecular structure:
(1)SMILES: Fc1ccc(cc1)C(=O)CCCN4C/C=C(/N3c2ccccc2NC3=O)CC4
(2)InChI: InChI=1/C22H22FN3O2/c23-17-9-7-16(8-10-17)21(27)6-3-13-25-14-11-18(12-15-25)26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-5,7-11H,3,6,12-15H2,(H,24,28)
(3)InChIKey: RMEDXOLNCUSCGS-UHFFFAOYAS

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 223ug/kg/12D- (0.223mg/kg) BEHAVIORAL: WAKEFULNESS

BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE WEAKNESS
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 93, 1972.
man TDLo intravenous 133ug/kg (0.133mg/kg) BEHAVIORAL: COMA Journal of Clinical Psychiatry. Vol. 47, Pg. 94, 1986.
mouse LD oral > 160mg/kg (160mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 13, Pg. 205, 1963.
mouse LD50 intraperitoneal 72mg/kg (72mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Zhonghua Mazuixue Zazhi. Chinese Journal of Anesthesiology. Vol. 5(2), Pg. 65, 1985.
mouse LD50 intravenous 20mg/kg (20mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 13, Pg. 205, 1963.
mouse LD50 subcutaneous 125mg/kg (125mg/kg)   Toxicology and Applied Pharmacology. Vol. 6, Pg. 63, 1964.
rat LD50 intravenous 30mg/kg (30mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 13, Pg. 205, 1963.
rat LD50 oral 750mg/kg (750mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 subcutaneous > 100mg/kg (100mg/kg)   Drugs in Japan Vol. 6, Pg. 533, 1982.

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