Ethopropazine Hydrochloride Chemical Properties

Melting point:

223-225° (some decompn)

storage temp. 

2-8°C

solubility 

DMSO: >5mg/mL at ~60°C, clear

form 

powder

color 

white

Merck 

13,3783

Stability:

Hygroscopic

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

RTECS 

SO5002000

Toxicity

LD50 s.c. in mice: 670 mg/kg (Farquharson, Johnston)

Ethopropazine Hydrochloride Usage And Synthesis

Originator

Parsidol,Warner Lambert,US,1954

Uses

Ethopropazine hydrochloride is a drug that shifts energy metabolism from mitochondrial respiration to glycolysis.

Uses

Antiparkinsonian;Anticholinergic

Definition

ChEBI: The monohydrochloride salt of profenamine. An antimuscarinic, it is used for the symptomatic treatment of Parkinson's disease.

Manufacturing Process

6.2 grams of phenthiazine in 100 cc of warm dry benzene was added during 1 hour with stirring, and in an atmosphere of hydrogen, to the Grignard reagent prepared from 1 gram of magnesium, 6.2 grams of methyl iodide, and 20 cc of dry ether. After boiling for 30 minutes, a solution of 6.6 grams of 2-chloro- 1-diethylamino propane in 10 cc of dry benzene was added during 1 hour to the boiling solution, and heating was maintained for a further 1.5 hours.
The reaction mixture was then cooled and treated with aqueous ammonium chloride and chloroform added to dissolve an oil at the interface of the benzene and aqueous layers. The chloroform-benzene extract was extracted with 2 N hydrochloric acid and the acid extract was basified at 5° to 10°C with 50% aqueous sodium hydroxide.
There was obtained a mixture of N-(2'-diethylamino-2'- methylethyl)phenthiazine and N-(2'-diethylamino-1'-methylethyl)phenthiazine in the form of a viscous yellow oil, BP 202° to 205°C/2 mm. This oil was treated in ethereal solution with ethereal hydrogen chloride and gave a white solid which was fractionally crystallized from ethylene dichloride. The less soluble fraction, N-(2'-diethylamino-2'-methylethyl)phenthiazine hydrochloride formed colorless rhombs, MP 223° to 225°C. The more soluble N-(2'- diethylamino-1'-methylethyl)phenthiazine hydrochloride was obtained as colorless prismatic needles, MP 166° to 168°C.

Therapeutic Function

Antiparkinsonian

General Description

Ethopropazinehydrochloride, 10-[2-(diethylamino)propyl]phenothiazinemonohydrochloride (Parsidol), introduced to therapy in1954, has antimuscarinic activity and is especially useful inthe symptomatic treatment of parkinsonism. In this capacity,it has value in controlling rigidity, and it also has a favorableeffect on tremor, sialorrhea, and oculogyric crises.

Biochem/physiol Actions

Ethoproprazine hydrochloride is an inhibitor of butyrylcholinesterase; antiparkinsonian. It reduces extrapyramidal motor effects, characteristic of Parkinson′s disease; also alleviates thermal hyperalgesia in rats.

Clinical Use

Ethopropazine Hydrochloride is oftenused in conjunction with other antiparkinsonian drugs forcomplementary activity.Side effects are common with this drug but are usuallynot severe. Drowsiness and dizziness are the most commonside effects at ordinary dosage levels, and as the dose increases,xerostomia, mydriasis, and others become evident.It is contraindicated in conditions such as glaucoma becauseof its mydriatic effect.

Ethopropazine Hydrochloride(1094-08-2)Related Product Information

• 2-Aminoethylammonium chloride
• diethazine
• Phenothiazine
• 10-METHYLPHENOTHIAZINE
• 2-(Phenylthio)aniline
• Ethopropazine Hydrochloride
• 1-(DIMETHYLAMINO)ISOPROPYLAMINE
• N-Methyldiphenylamine
• Promethazine hydrochloride
• ETHOPROPAZINE
• fenethazine
• Diphenyl sulfide
• DIPHENYLAMINE HYDROCHLORIDE
• N,N,N',N'-TETRAMETHYL-1,2-DIAMINOPROPANE
• N-(2-amino-1-methylethyl)-N,N-diethylamine
• N,N-DIETHYL-N',N'-DIMETHYLETHYLENE DIAMINE
• N,N-DIETHYL-N'-PHENYLETHYLENEDIAMINE
• N-MONODESMETHYL PROMETHAZINE