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341-69-5

Basic Information
CAS No.: 341-69-5
Name: ORPHENADRINE HYDROCHLORIDE
Molecular Structure:
Molecular Structure of 341-69-5 (ORPHENADRINE HYDROCHLORIDE)
Formula: C18H23 N O . Cl H
Molecular Weight: 305.848
Synonyms: Ethanamine,N,N-dimethyl-2-[(2-methylphenyl)phenylmethoxy]-, hydrochloride (9CI);Ethylamine, N,N-dimethyl-2-[(o-methyl-a-phenylbenzyl)oxy]-, hydrochloride (8CI); (?à)-Orphenadrine hydrochloride;2-(Dimethylamino)ethyl 2-methylbenzhydryl ether hydrochloride; Brocasipal;Disipal; Disipal hydrochloride; Mebedrol; Mefenamin hydrochloride; Mephenamin;Mephenamin hydrochloride; Mephenamine; Mephenamine hydrochloride;N,N-Dimethyl-2-(o-methyl-a-phenylbenzyloxy)ethylamine hydrochloride; NSC 82357; Orfenadrinhydrochloride; Orphenadrine hydrochloride
EINECS: 206-435-4
Density: 1.014g/cm3
Melting Point: 156 - 157 C
Boiling Point: 363°Cat760mmHg
Flash Point: 107.1°C
Solubility: Toxicity data moderate

Stability

    Stable. Incompatible with strong oxidizing agents.

Toxicology

    Toxic if swallowed or absorbed through the skin. May be harmful if inhaled.

    Toxicity data

Appearance: white crystalline powder
Hazard Symbols:
Risk Codes: 22
Safety: Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human systemic effects: mydriasis (pupillary dilation), 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.
PSA: 12.47000
LogP: 4.46460
Synthetic route
7677-24-9

trimethylsilyl cyanide

341-69-5

orphenadrine hydrochloride

A

802577-40-8

2-(methyl(2-(phenyl(2-methylphenyl)methoxy)ethyl)amino)acetonitrile

B

C19H22N2O

Conditions
ConditionsYield
With rose bengal In water at 20℃; for 24h; pH=14; Irradiation; Overall yield = 52%; Overall yield = 1 g;
341-69-5

orphenadrine hydrochloride

A

(S)-orphenadrine

B

33425-91-1

(R)-N,N-dimethyl-N-{2-[1-(2-methylphenyl)-1-phenylmethoxy]ethyl}amine

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

Chemistry informtion about Orphenadrine Hydrochloride (CAS NO.341-69-5) is:
IUPAC Name: N,N-Dimethyl-2-[(2-Methylphenyl)-Phenylmethoxy]Ethanamine Hydrochloride
Synonyms: 2-Dimethylaminoethyl 2-Methylbenzhydryl Ether Hydrochloride ; 2-Dimethylaminoethyl2-Methylbenzhydryletherhydrochloride ; Bf 5930 ; Bg 5930 ; Brocadisipal ; Brocasipal ; Bs 5930 ; Disipal Hydrochloride
Product Categories: API
MF: C18H24ClNO
MW: 305.84
EINECS: 206-435-4 
Flash Point: 107.1 °C
Boiling Point: 363 °C at 760 mmHg
Vapour Pressure: 1.86E-05 mmHg at 25°C
Enthalpy of Vaporization: 60.9 kJ/mol
Storage temp.: 2-8°C
Stability: Stable. Incompatible with strong oxidizing agents.
Following is the molecular structure of Orphenadrine Hydrochloride (CAS NO.341-69-5) is:

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 33mg/kg (33mg/kg) brain and coverings: increased intracranial pressure Archiv fuer Toxikologie. Vol. 25, Pg. 76, 1969.
guinea pig LD50 subcutaneous 74mg/kg (74mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 373, 1972.
man TDLo oral 71mg/kg (71mg/kg) sense organs and special senses: mydriasis (pupillary dilation): eye behavioral: "hallucinations, distorted perceptions" cardiac: pulse rate increase without fall in bp Human Toxicology. Vol. 4, Pg. 331, 1985.
mouse LD50 intraperitoneal 65mg/kg (65mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 373, 1972.
mouse LD50 intravenous 20mg/kg (20mg/kg) behavioral: convulsions or effect on seizure threshold behavioral: changes in motor activity (specific assay) behavioral: ataxia Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 72, 1955.
mouse LD50 oral 100mg/kg (100mg/kg) behavioral: convulsions or effect on seizure threshold behavioral: changes in motor activity (specific assay) behavioral: ataxia Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 72, 1955.
mouse LD50 subcutaneous 88mg/kg (88mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 373, 1972.
rat LD50 intraperitoneal 93mg/kg (93mg/kg) lungs, thorax, or respiration: respiratory stimulation Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 28, 1969.
rat LD50 intravenous 27500ug/kg (27.5mg/kg) behavioral: convulsions or effect on seizure threshold behavioral: changes in motor activity (specific assay) behavioral: ataxia Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 72, 1955.
rat LD50 oral 255mg/kg (255mg/kg) behavioral: altered sleep time (including change in righting reflex) behavioral: convulsions or effect on seizure threshold behavioral: tremor Gendai no Rinsho. Vol. 2, Pg. 311, 1968.
rat LD50 subcutaneous 230mg/kg (230mg/kg) behavioral: convulsions or effect on seizure threshold behavioral: ataxia behavioral: changes in motor activity (specific assay) Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 72, 1955.
women TDLo oral 150mg/kg (150mg/kg) behavioral: convulsions or effect on seizure threshold behavioral: coma lungs, thorax, or respiration: dyspnea Archiv fuer Toxikologie. Vol. 23, Pg. 264, 1968.

Safety Profile

Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human systemic effects: mydriasis (pupillary dilation), 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. 
Hazard Codes:
HarmfulXn
Risk Statements:
R22:Harmful if swallowed.
Safety Statements:
S36:Wear suitable protective clothing.
RIDADR: 3249
RTECS: KR6300000
HazardClass: 6.1(b)
PackingGroup: III

Analytical Methods

The citrate salt of orphenadrine is available as Norflex, Banflex, Flexon, and X-Otag, and the hydrochloride salt is available as Disipal and Mephenamin.
In the United States and Canada, orphenadrine citrate is supplied as 100 mg controlled-release tablets, 100 mg immediate-release tablets, and 60 mg immediate-release tablets. Orphenadrine hydrochloride is supplied as 50 and 60 mg tablets, a 10 mg/ml oral solution and 30 mg/ml solution for injection.
Orphenadrine Hydrochloride is also available mixed with aspirin, paracetamol (Anarex), ibuprofen, caffeine, and/or codeine in many places. All Orphenadrine Hydrochloride preparations require a prescription in the United States and the various oral forms are over the counter in Canada; It is also available in many European and Pacific Rim countries (including Australia), by prescription in all of them except Belgium, Mexico and Canada where single-ingredient and combination products are available over the counter. It is available over the counter in the Philippines as Norgesic (35 mg Orphenadrine Citrate/450 mg Paracetamol) and Norgesic Forte (50 mg Orphenadrine Citrate/650 mg Paracetamol) from 3M Pharmaceuticals. Orphenadrine is not available at this time in Japan, Slovenia, Croatia, China, France and Spain.

Specification

Orphenadrine Hydrochloride (CAS NO.341-69-5) is odorless white or almost white crystalline powder. pH (aqueous solution) about 5.5. It is bitter numbing taste. It may be sensitive to prolonged exposure to light and air and it soluble in water. It is incompatible with strong oxidizers. Flash point data for it is not available; however, it is probably combustible.Orphenadrine Hydrochloride has been manufactured at the SAFC Arklow facility since 1988.