Difenidol hydrochloride Chemical Properties

Melting point:

212-214°

storage temp. 

2-8°C

solubility 

DMSO (Slightly, Sonicated), Methanol (Slightly)

form 

Solid

color 

White to Off-White

PH

pH (10g/l, 25℃) : 4.7～6.5

Water Solubility 

H2O: 2mg/mL, clear (warmed)

Merck 

14,3311

InChI

InChI=1S/C21H27NO/c23-21(19-11-4-1-5-12-19,20-13-6-2-7-14-20)15-10-18-22-16-8-3-9-17-22/h1-2,4-7,11-14,23H,3,8-10,15-18H2

InChIKey

OGAKLTJNUQRZJU-UHFFFAOYSA-N

SMILES

C(O)(CCCN1CCCCC1)(C1=CC=CC=C1)C1C=CC=CC=1

CAS DataBase Reference

3254-89-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

36

WGK Germany 

3

RTECS 

TM4970500

HS Code 

2933.39.9200

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

Toxicity

LD50 oral in rat: 515mg/kg

MSDS

• Language:English Provider:SigmaAldrich

Difenidol hydrochloride Usage And Synthesis

Chemical Properties

White Solid

Uses

Diphenidol is an muscarinic antagonist is an antivertigo agent. Diphenidol displays heart arrhythmia inhibition and parasympatholytic activity.

Definition

ChEBI: Difenidol hydrochloride is a diarylmethane.

brand name

Vontrol (GlaxoSmithKline).

Biological Activity

Diphenidol is a non-selective muscarinic acetylcholine receptor antagonist. Diphenidol is an antiemetic agent used in the treatment of vomiting and vertigo.

Synthesis

Difenidol hydrochloride is synthesized in three steps. S1: Preparation of 1-(3-chloropropyl)hexahydropyridine: 1,3-Bromochloropropane reacts with hexahydropyridine at room temperature. Liquid base is then added. After layering, the oily layer is collected and dried to give the intermediate. S2: Preparation of ??,??-diphenyl-1-piperidinobutanol: After initiation with magnesium, a THF solution of intermediate N-(3-chloropropyl)piperidine is added dropwise, followed by a THF solution of benzophenone. After holding, the mixture is poured into ice-cold ammonium chloride solution for hydrolysis. Filtration and drying yield the product. S3: Preparation of ??,??-diphenyl-1-piperidinobutanol hydrochloride: The product from step 2 is dissolved in acetone. After decolorization, hydrochloric acid is added dropwise to form the salt. Gradient cooling induces crystallization. Filtration and drying give the final product.

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