 Home > Encyclopedia > (±)-Mephenesin

(±)-Mephenesin

(±)-Mephenesin structure

CAS No:
59-47-2
Formula:
C10H14O3
Chemical Name:
(±)-Mephenesin
Synonyms:
1,2-Propanediol,3-(2-methylphenoxy)-;1,2-Propanediol,3-(o-tolyloxy)-;3-(2-Methylphenoxy)-1,2-propanediol;BDH 312;RP 3602;Atensin;Avosyl;o-Cresyl α-glyceryl ether;Daserol;Decontractyl;1,2-Dihydroxy-3-(2-methylphenoxy)propane;Dioloxol;Glykresin;Glyotol;Kinavosyl;Lissephen;Mephedan;Mephelor;Mephenesin;Mephenesine;Mephensin;Mepherol;Mephson;3-(o-Methylphenoxy)-1,2-propanediol;Myanesin;Myanol;Myasin;Mycocuran;Myodetensine;Myopan;Myoserol;Myoten;Myoxane;Oranixon;Prolax;Relaxar;Relaxil;Sinan;Spartoloxyn;Spasmolyn;Stilalgin;Thoxidil;Tolansin;Tolax;Tolcil;Tolhart;Tolosate;Toloxyn;3-o-Toloxy-1,2-propanediol;Tolserol;Tolseron;Tolsin;Tolulexin;Tolulox;Tolyspaz;Cresoxydiol;3-(o-Tolyloxy)-1,2-propanediol;Glyceryl o-tolyl ether;o-Cresyl glycerol ether;Cresoxypropanediol;Avoxyl;Curythan;Memphenesin;Mephesin;Myolysin;Renarcol;Sansdolor;Walconesin;Mervaldin;Mephin;Daserd;Myodetensin;3-(2-Tolyloxy)-1,2-propanediol;3-(2-Methylphenoxy)propane-1,2-diol;(±)-Mephenesin;Rhex;NSC 25234;NSC 36140;NSC 50788;NSC 8134;118205-96-2
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Mephenesin is an NMDA receptor antagonist, is a centrally acting muscle relaxant.Target: NMDA receptor

1-(2-methylphenyl)glycerol is a glycerol ether in which a single 2-methylphenyl group is attached at position 1 of glycerol via an ether linkage. It is an aromatic ether and a glycerol ether. It derives from an o-cresol.|Mephenesin is a synthetic cresol glyceryl ether which produces transient muscle relaxation and paralysis via central nervous system depression. It first entered use in the 1950s.|A centrally acting muscle relaxant with a short duration of action.

(±)-Mephenesin Basic Attributes

Molecular Weight：

182.22

Exact Mass：

182.22

EC Number：

200-427-4

NSC Number：

757857|50788|36140|25234|8134

DSSTox ID：

DTXSID4023254

ATC Code：

M - Musculo-skeletal system

HScode：

2909309090

Characteristics

PSA：

49.7

XLogP3：

1.4

Density：

1.152g/cm3

Melting Point：

70 °C (decomp)

Boiling Point：

180-184 °C @ Press: 9 Torr

Flash Point：

153-154°C/4mm

Refractive Index：

1.545

Water Solubility：

H2O: Sparingly soluble ;soluble in alcohol

Toxicity：

LD50 in mice, rats, hamsters (mg/kg): 471, 283, 322 i.p.; 990, 945, 821 orally (Roszkowski); LD50 in mice (mM/kg): 2.83 i.p.; 10.53 orally (Dresel, Slater)

Safety Information

wgk germany：

hazard class code：

22-36

safety instructions：

RTECS Number：

TZ1225000

Marks：

Precautionary statement(s)：

P264, P270, P280, P301+P312, P305+P351+P338, P330, P337+P313, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P305+P351+P338, P330, P337+P313, and P501|Aggregated GHS information provided by 47 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Mephenesin can produce hemolysis leading to hemoglobinuria with intravenous administration of concentrations greater than 10%. As a central nervous system depressant it can also produce paralysis and respiratory depression.

Drug Information

Drug Indication：

Mephenesin was used for the treatment of muscle spasticity in diseases like Parkinson's or Multiple Sclerosis.

Pharmacology：

Mephenesin reduced neuronal excitability leading to decreases action potentials to muscle fibers which ultimately produces a reduction in spasticity.

MeSH：

A heterogeneous group of drugs used to produce muscle relaxation, excepting the neuromuscular blocking agents. They have their primary clinical and therapeutic uses in the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. They have been used also for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in MULTIPLE SCLEROSIS. (From Smith and Reynard, Textbook of Pharmacology, 1991, p358) (See all compounds classified as Muscle Relaxants, Central.)

Mechanism of Action：

The exact mechanism of action of mephenesin is not known. It has been observed to block both inward sodium and inward calcium currents in neurons. It has a physiological effect which opposes that of strychnine.

MeSH Entry Terms：

Décontractyl

(±)-Mephenesin Use and Manufacturing

Methods of Manufacturing

Sodium hydroxide (0.37 g) and tetrabutylammonium bromide (0.30 g) were added to 2-methylphenol (1.00 g) and stirred at room temperature. Glycidol (0.75 g) was added and stirred again at 50 ° C for 5 hours The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue (1.49 g) was purified by silica gel column chromatography Respectively. Eluting with a mixture of hexane / ethyl acetate = 1/1, and concentration under reduced pressure to obtain the product (0.47 g). The obtained product was confirmed to be a compound having UV absorption by HPTLC analysis and is considered to be 1, 2-di-hydroxy-3- (2'-methylphenoxy) propyl represented by the following structural formula from the raw material.

Uses

muscle relaxant (skeletal)

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:182.22
XLogP3:1.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:182.094294304
Monoisotopic Mass:182.094294304
Topological Polar Surface Area:49.7
Heavy Atom Count:13
Complexity:138
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of (±)-Mephenesin

Henan Lihao Chem Plant Limited Contact Supplier

CN
5 YRS

Business licensed

Trader Supplier of PVC resin,pvc paste resin,melamine

high quality 1-Bromo-3,5-dimethyladamantane 99% transparent liquid KANBEI

CAS No.: 59-47-2

Grade: Industrial Grade

Content: 99%

Inquiry