Mephenesin

HCID 4059

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Basic information

CAS: 59-47-2
Standard SMILES: Cc1ccccc1OCC(O)CO
InChIKey: JWDYCNIAQWPBHD-UHFFFAOYSA-N
Molecular formula: C10H14O3
Average molar mass: 182.22 g/mol
Monoisotopic mass: 182.0942943

Overview

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 a glycerol ether and an aromatic ether. It is functionally related to an o-cresol.

Names & identifiers

Preferred name: Mephenesin
IUPAC: 3-(2-methylphenoxy)propane-1,2-diol
English name: Mephenesin
Molecular formula: C10H14O3
Molecular weight: 182.22

Names & synonyms

mephenesin59-47-2MephenesineTolserol3-(2-Methylphenoxy)propane-1,2-diolCresoxydiolMefenesinaMephenesinum3-(o-Methylphenoxy)-1,2-propanediolDTXSID4023254NSC-252347B8PIR2954

Show more names

MephensinRhexSinanTolaxXerala1141OrtolA 1141DaserdGlytol

DTXCID803254(+-)-MephenesinRefChem:810990M03BX06200-427-4DecontractylDioloxolLissephen

Database identifiers

CAS: 59-47-2
PubChem CID: 4059
DTXSID: DTXSID4023254
ChEMBL: CHEMBL229128
ChEBI: CHEBI:94398
UNII: 7B8PIR2954
EC Number: 200-427-4
Nikkaji: J46.973D

Properties

Computed structural properties

XLogP: 1.4
Topological polar surface area: 49.7 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 4
Heavy atoms: 13
Formal charge: 0
Complexity: 138

Experimental & physicochemical properties

DrugsPharmaceuticals -> Antipsychotics

LogP1.41

SolubilitySparingly soluble

Human DrugsPharmaceuticals

Physicochemical properties

Melting point: 69 · 69-71 °C(lit.)
Boiling point: 153 · 153-154 °C4 mm Hg(lit.)
Density: 1.0966 · 1.0966 (rough estimate)
refractive index: 1.532 · 1.5320 (estimate)
Flash point: 153 · 153-154°C/4mm
storage temp.: Sealed in dry,Room Temperature
solubility: Soluble in alcohol
pka: 13.52 · 13.52±0.20(Predicted)
form: Solid
color: White
Merck: 14 · 14,5850
EWG's Food Scores: 1 · 1
FDA UNII: 7 B8PIR2954 · 7B8PIR2954
ATC code: 3 BX06 · M03BX06
Symbol(GHS): 6 · GHS06
Signal word: Warning
Hazard statements: 301 · H301
Precautionary statements: 264 · P264-P270-P301+P310a-P321-P405-P501a
Hazard Codes: Xn
Risk Statements: 22 · 22-36
Safety Statements: 26 · 26
WGK Germany: 2 · 2
RTECS: 1225000 · TZ1225000
HS Code: 2909498090 · 2909498090
Toxicity: 50 in · 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 & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information1,2-Propanediol, 3-(2-methylphenoxy)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

wgk: 2
rtecs: TZ1225000
hs_code: 2909498090
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)
risk_code: 22-36
Signal word: Warning
Symbol(GHS): GHS06
hazard_code: Xn
safety_code: 26
Hazard statements: H301
Precautionary statements: P264-P270-P301+P310a-P321-P405-P501a

Chemistry & industry

Pharmacology

ATC Code · 2 items

M - Musculo-skeletal system

QM - Musculo-skeletal system

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

Mechanism of ActionThe 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 Pharmacological Classification · 1 item

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)

Uses & manufacturing

Use ClassificationPharmaceuticals

Applications

Usesmuscle relaxant (skeletal)

UsesMephenesin was used in the study of ligand-based virtual screening and design of antimalarial compounds.

Upstream & downstream products

Upstream raw materials

Suppliers67 total

郑州阿尔法化工有限公司+86-18530059196 · [email protected]

艾吉析科技（上海）有限公司17717235263 · [email protected]

河南赢创生物科技有限公司16650615803 · [email protected]

Suzhou ARTK Medchem Co., Ltd.+86-18168183658 · [email protected]

河北创海生物科技有限公司+86-86-13131129325 · [email protected]

Additional notes · 1 item

DefinitionChEBI: 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 is functionally related to an o-cresol.

Related reactions

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Compound notes

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