Orphenadrine Chemical Properties

Melting point:

25°C

Boiling point:

bp12 195°

Density 

1.0278 (rough estimate)

refractive index 

1.5740 (estimate)

pka

pKa 8.4 (Uncertain)

Water Solubility 

1.801mg/L(22.5 ºC)

CAS DataBase Reference

83-98-7

Safety Information

RIDADR 

1851

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

83-98-7(Hazardous Substances Data)

Toxicity

LD50 oral in mouse: 125mg/kg

Orphenadrine Usage And Synthesis

Originator

Norflex,Riker,US,1959

Uses

Relaxant (skeletal muscle); antihistaminic.

Definition

ChEBI: A tertiary amino compound which is the phenyl-o-tolylmethyl ether of 2-(dimethylamino)ethanol.

Manufacturing Process

As described in US Patent 2,567,351, o-methylbenzhydryl bromide is added slowly to β-dimethylaminoethanol at refluxing temperature. After the addition has been completed the mixture is refluxed and stirred for an additional 16 hours. The mixture is cooled and the bottom layer consisting of the crude hydrobromide salt of β-dimethylaminoethanol is drawn off. The excess amino alcohol is distilled from the upper layer in vacuo and the residue is reacted with citric acid.

brand name

Norflex (3M Pharmaceuticals).

Therapeutic Function

Muscle relaxant

Enzyme inhibitor

This muscle relaxant and antihistaminic agent (FWfree-base = 269.39 g/mol; CAS 83-98-7) is both a muscarinic and histamine H1 receptor antagonist that also inhibits some cytochrome P450 systems. Classified as an anticholinergic drug (with 58% as potent as atropine) and an ethanolamineclass antihistamine, it also inhibits the noradrenergic transporter and NMDA receptor ion channel (Ki ≈ 6 μM). Commercially available as either the hydrochloride or citrate salt, orphenadrines used to relieve pain of muscle injuries, such as strains and sprains. Target(s): aldehyde oxidase; CYP1A2; CYP2A6; CYP3A4; CYP2B; CYP2B6; CYP2C9; CYP2C19; CYP2D6; histamine H1 receptor; N-methyl-D-aspartate (NMDA) receptor; muscarinic receptor; noradrenaline reuptake.

Orphenadrine(83-98-7)Related Product Information

• Toluenesulfonamide
• o-Toluic acid
• O-toluenediamine
• Bufenadrine
• Oxitriptyline
• Ciheptolane
• Orphenadrine citrate
• N-METHYLORPHENADRINE METHOSULFATE
• 2-(PHENYL-O-TOLYLMETHOXY)ETHYLDIMETHYLAMINE HYDROCHLORIDE
• m-(alpha-(2-(Dimethylamino)ethoxy)-o-methylbenzyl)phenol maleate
• SPECS AE-641/11703040
• spiroxepin
• Orphenadrine