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| | Ethopropazine Hydrochloride Basic information |
| Product Name: | Ethopropazine Hydrochloride | | Synonyms: | lysivanehydrochloride;n,n-diethyl-alpha-methyl-10h-phenothiazine-10-ethanaminmonohydrochloride;n,n-diethyl-alpha-methyl-10-phenothiazineethylaminhydrochloride;profenaminemonohydrochloride;ethopropazine hcl;10H-Phenothiazine-10-ethanamine, N,N-diethyl-.alpha.-methyl-, monohydrochloride;10H-Phenothiazine-10-ethanamine, N,N-diethyl-a-methyl-, monohydrochloride (9CI);NSC 169467 | | CAS: | 1094-08-2 | | MF: | C19H25ClN2S | | MW: | 348.93 | | EINECS: | 214-134-4 | | Product Categories: | | | Mol File: | 1094-08-2.mol |  |
| | 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 | | InChI | 1S/C19H24N2S.ClH/c1-4-20(5-2)15(3)14-21-16-10-6-8-12-18(16)22-19-13-9-7-11-17(19)21;/h6-13,15H,4-5,14H2,1-3H3;1H | | InChIKey | VXPCQISYVPFYRK-UHFFFAOYSA-N | | SMILES | Cl[H].CCN(CC)C(C)CN1c2ccccc2Sc3ccccc13 |
| Hazard Codes | Xn | | Risk Statements | 22 | | WGK Germany | 3 | | RTECS | SO5002000 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral | | 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 Preparation Products And Raw materials |
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