341-69-5

Basic information

• Product Name: ORPHENADRINE HYDROCHLORIDE
• Synonyms: 2-Dimethylaminoethyl 2-methylbenzhydryl ether hydrochloride;2-dimethylaminoethyl2-methylbenzhydryletherhydrochloride;BF 5930;BG 5930;Brocadisipal;Brocasipal;BS 5930;Disipal hydrochloride
• CAS NO: 341-69-5
• Molecular Formula: C₁₈H₂₃NO*ClH
• Molecular Weight: 305.84
• EINECS: 206-435-4
• Product Categories: API
• Mol File: 341-69-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: 159.0 to 164.0 °C
• Boiling Point: 363°Cat760mmHg
• Flash Point: 107.1°C
• Appearance: white crystalline powder
• Density: 1.014g/cm³
• Vapor Pressure: 1.86E-05mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Freely soluble in water and in ethanol (96 per cent).
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 3745818
• CAS DataBase Reference: ORPHENADRINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ORPHENADRINE HYDROCHLORIDE(341-69-5)
• EPA Substance Registry System: ORPHENADRINE HYDROCHLORIDE(341-69-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36
• RIDADR: 3249
• WGK Germany: 3
• RTECS: KR6300000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 341-69-5(Hazardous Substances Data)

Usage

Chemical Properties

White or almost white, crystalline powder.

Definition

ChEBI: A hydrochloride comprising equimolar amounts of ophenadrine and hydrogen chloride.

General Description

Odorless white or almost white crystalline powder. pH (aqueous solution) about 5.5. Bitter numbing taste.

Air & Water Reactions

May be sensitive to prolonged exposure to light and air. Water soluble.

Reactivity Profile

ORPHENADRINE HYDROCHLORIDE is incompatible with strong oxidizers.

Fire Hazard

Flash point data for ORPHENADRINE HYDROCHLORIDE are not available; however, ORPHENADRINE HYDROCHLORIDE is probably combustible.

Biochem/physiol Actions

Muscarinic receptor antagonist; H1 histamine receptor antagonist; muscle relaxant. Orphenadrine has also been reported to inhibit the noradrenergic transporter and to block the NMDA receptor ion channel.

Clinical Use

Anti-muscarinic: Parkinsonism Drug induced extra-pyramidal symptoms

Safety Profile

Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human systemic effects: mydriasis @updlaryd ilation), hallucinations, distorted perceptions, pulse rate increase, intracranial pressure increase. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx and HCl

Drug interactions

Potentially hazardous interactions with other drugs None known

Metabolism

Orphenadrine is almost completely metabolised to at least 8 metabolites in the liver. It is mainly excreted in the urine as metabolites and small amounts of unchanged drug

InChI:InChI=1/C18H23NO/c1-15-9-7-8-12-17(15)18(20-14-13-19(2)3)16-10-5-4-6-11-16/h4-12,18H,13-14H2,1-3H3/p+1/t18-/m0/s1

Synthetic route

trimethylsilyl cyanide (7677-24-9) + orphenadrine hydrochloride (341-69-5) → 2-(methyl(2-(phenyl(2-methylphenyl)methoxy)ethyl)amino)acetonitrile (802577-40-8) + C19H22N2O

Conditions	Yield
With rose bengal In water at 20℃; for 24h; pH=14; Irradiation; Overall yield = 52%; Overall yield = 1 g;

orphenadrine hydrochloride (341-69-5) → (S)-orphenadrine + (R)-N,N-dimethyl-N-{2-[1-(2-methylphenyl)-1-phenylmethoxy]ethyl}amine (33425-91-1)

Conditions	Yield
With Chiralcel OD-RH column In acetonitrile at 20℃; for 0.116667h; pH=9; Resolution of racemate;

Downstream Products

• 33425-91-1 (R)-N,N-dimethyl-N-{2-[1-(2-methylphenyl)-1-phenylmethoxy]ethyl}amine 
• 802577-40-8 2-(methyl(2-(phenyl(2-methylphenyl)methoxy)ethyl)amino)acetonitrile