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| | Eperisone hydrochloride Basic information | | Synthesis |
| | Eperisone hydrochloride Chemical Properties |
| Melting point | 169-171°C | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Methanol (Slightly), Water (Slightly) | | form | Solid | | color | White | | InChI | InChI=1S/C17H25NO.ClH/c1-3-15-7-9-16(10-8-15)17(19)14(2)13-18-11-5-4-6-12-18;/h7-10,14H,3-6,11-13H2,1-2H3;1H | | InChIKey | GTAXGNCCEYZRII-UHFFFAOYSA-N | | SMILES | C1(=CC=C(CC)C=C1)C(=O)C(C)CN1CCCCC1.Cl | | CAS DataBase Reference | 56839-43-1(CAS DataBase Reference) |
| WGK Germany | WGK 3 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral | | Toxicity | LD50 in male S.D. rats, Wistar rats, mice (mg/kg): 1300, 1850, 1024 orally (Miyagawa) |
| | Eperisone hydrochloride Usage And Synthesis |
| Synthesis | The product was synthesized by reacting p-ethylphenylacetone (2) with guanethidine hydrochloride via the Mannieh reaction, as shown in Figure 1:
Figure 1 shows the reaction route for the synthesis of ethylperisone hydrochloride
Synthesis method:
1. Synthesis of p-ethylphenylacetone (2)
Propyl chloride (100g, 1.08 mol) was added. After treatment, the reaction solution was distilled under reduced pressure after recovering petroleum ether and excess ethylbenzene. The fraction at bP112-114 ℃/1.33kPa was collected to obtain 2.
2. Synthesis of ethylparaben (1)
Take freshly distilled ethylparaben (20.2 g, 0.24 mol), add anhydrous ethanol (20 ml), add concentrated hydrochloric acid dropwise at low temperature to pH 4-5, evaporate the ethanol under reduced pressure, then add anhydrous ethanol (50 ml), p-ethyl acetone (32.4 g, 0.2 mol), 36% formaldehyde solution (42.0 g, 0.5 mol) and concentrated hydrochloric acid (1 ml), stir and reflux for 8 h, evaporate the solvent, dissolve the residue in 10% sodium hydroxide solution, extract with ether, wash the extract with water, dry, and pass hydrogen chloride through in an ice-water bath to pH 2-3. Filter out the generated solid, recrystallize with ethanol-acetone to obtain 1 colorless crystal. | | Description | Eperisone hydrochloride is a centrally acting muscle relaxant useful in the
management of various spastic conditions including cervical spondylosis and
cerebral palsy. It is structurally related to tolperisone. | | Chemical Properties | White Solid | | Originator | Eisai (Japan) | | Uses | Used as antispasmodic | | Uses | A spasmolytic agent related structurally to Tolperisone (T535475). Muscle relaxant (skeletal). | | Application | Clinically, eperisone hydrochloride is widely used to treat various symptoms of muscle tension. For instance, in orthopedics, it is frequently employed to alleviate pain and muscle tension resulting from fractures, dislocations, and muscle strains; in neurology, it is used to treat muscle rigidity and spasms associated with conditions such as Parkinson's disease and multiple sclerosis; and in rehabilitation medicine, it helps improve the recovery of muscle function following sports injuries. | | Definition | ChEBI: Eperisone hydrochloride is an aromatic ketone. | | Manufacturing Process | To 60 ml of isopropanol, there are introduced 120 g of 4-ethyl-propiophenone,
28.8g of p-formaldehyde and 107 g of piperidine hydrochloride, and the
resulting mixture is heated to reflux on an oil bath with stirring. The heating is
continued, and when the reaction mixture solidifies, the state being a sign of
completion of the reaction, there are added 500 ml of acetone thereinto. The
solidified mass is pulverized by crush, recovered by filtration and washed with
acetone. 144 g of the crude dry crystalline substance is thus obtained, which
is the hydrochloride of the purposed product. The hydrochloride is
recrystallized from isopropanol, and there are obtained the crystalline needles
having the melting point of 170°C to 172°C. | | Brand name | MYONAL | | Therapeutic Function | Muscle relaxant | | Mechanism of action | Eperisone hydrochloride treats symptoms of hypertonia by acting on the central nervous system to relax skeletal muscles and directly relax vascular smooth muscle. It primarily affects spinal reflexes and gamma motor neurons, effectively inhibiting spinal reflexes and muscle sensitivity, while simultaneously increasing blood circulation and suppressing pain reflexes. Chemicalbook is a multi-point muscle relaxant, acting on the vicious cycle of muscle rigidity (hypertonia → insufficient blood supply → pain → further increase in muscle tension) to relieve symptoms of hypertonia. Its key feature is the simultaneous relaxation of high-tension muscles, improved blood circulation, and reduction of accompanying pain. |
| | Eperisone hydrochloride Preparation Products And Raw materials |
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