MEPHENESIN

First approved in 1948

Details

Stereochemistry	RACEMIC
Molecular Formula	C10H14O3
Molecular Weight	182.2164
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=CC=C1OCC(O)CO

InChI

InChIKey=JWDYCNIAQWPBHD-UHFFFAOYSA-N

InChI=1S/C10H14O3/c1-8-4-2-3-5-10(8)13-7-9(12)6-11/h2-5,9,11-12H,6-7H2,1H3

HIDE SMILES / InChI

Molecular Formula	C10H14O3
Molecular Weight	182.2164
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.pharma-medicaments.com/media/3512060__017142000_1759_24052013.pdf
Curator's Comment: description was created based on several sources, including: http://www.medindia.net/doctors/drug_information/mephenesin.htm | https://www.ncbi.nlm.nih.gov/pubmed/18886031

Mephenesin is a centrally acting muscle relaxant. This medication is prescribed for muscle spasm. It can be used as an antidote for strychnine poisoning. Most common side effects are: lassitude, drowsiness, weakness, loss of appetite, nausea and vomiting, hypersensitivity reactions. Its clinical usefulness is considered to be limited by its brief duration of action.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate NMDA receptor 47 Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7912632 \| https://www.ncbi.nlm.nih.gov/pubmed/1378953	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Painful muscular contractions 1 Sources: https://www.pharma-medicaments.com/media/3512060__017142000_1759_24052013.pdf	Palliative		Approved 8583	Decontractyl Approved Use It is indicated for the supportive treatment of painful muscle contractions.

Doses

Dose	Population	Adverse events
500 mg single, oral Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/24814457	healthy, 25 years Health Status: healthy Age Group: 25 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/24814457	Disc. AE: Anaphylactic shock... AEs leading to discontinuation/dose reduction: Anaphylactic shock Sources: https://pubmed.ncbi.nlm.nih.gov/24814457
7.5 g single, oral Overdose Dose: 7.5 g Route: oral Route: single Dose: 7.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/17209942	healthy, 48 years Health Status: healthy Age Group: 48 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/17209942	Other AEs: Adverse event... Other AEs: Adverse event (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/17209942

AEs

AE	Significance	Dose	Population
Anaphylactic shock	Disc. AE	500 mg single, oral Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/24814457	healthy, 25 years Health Status: healthy Age Group: 25 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/24814457
Adverse event	grade 5	7.5 g single, oral Overdose Dose: 7.5 g Route: oral Route: single Dose: 7.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/17209942	healthy, 48 years Health Status: healthy Age Group: 48 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/17209942

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY562102	https://www.001chemical.com/chem/59-47-2
AA Blocks	AA00E9FU	http://www.aablocks.com/goods/Goods/detail?id=AA00E9FU
Aaron Chemicals	AR00EA7M	http://www.aaronchem.com/59-47-2
abcr GmbH	AB134044	http://www.abcr.com/shop/en/AB134044
AbMole Bioscience	M5769	http://www.abmole.com/products/mephenesin.html
Acadechem	ACDS-033174	http://www.acadechemical.com/product/107873
AK Scientific, Inc. (AKSCI)	W0052	http://www.aksci.com/item_detail.php?cat=W0052
Ark Pharm	AK546793	http://www.arkpharminc.com/products/59-47-2.html
BLD Pharm	BD137421	http://www.bldpharm.com/products/59-47-2.html
Chem Scene	CS-5340	http://www.chemscene.com/59-47-2.html
Chemspace	CSSB00011215453	https://chem-space.com/CSSB00011215453
Clearsynth	CS-DE-01388	https://www.clearsynth.com/en/CSDE01388.html
CSNpharm	CSN11379	https://www.csnpharm.com/products/mephenesin.html
DC Chemicals	DC34654	http://www.dcchemicals.com//product_show-Mephenesin.html
eNovation Chemicals	D669825	https://www.enovationchem.com/ProductDetails.asp?ProductID=D669825
Finetech	FT-0628209	http://www.finetechnology-ind.com/prod/detail/pub/59-47-2.html
iChemical	EBD70999	http://www.ichemical.com/products/59-47-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00196153	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00196153
LGC Standards	LGCFOR0810.00	https://www.lgcstandards.com/US/en/p/LGCFOR0810.00
LGC Standards	MM0810.00	https://www.lgcstandards.com/US/en/p/MM0810.00
mcule	MCULE-1125347766	https://mcule.com/MCULE-1125347766/
MedChem Express	HY-B1283	https://www.medchemexpress.com/Mephenesin.html
Molcore	MC562102	https://www.molcore.com/product/59-47-2
MuseChem	I004227	https://www.musechem.com/product/I004227.html
Sigma-Aldrich	286567_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/286567?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	S423300_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/s423300
Sinfoo Biotech	S017517	http://www.sinfoobiotech.com/product/1020915
Smolecule	S534976	http://www.smolecule.com/products/s534976
THE BioTek	bt-274757	https://www.thebiotek.com/product/inhibitors/bt-274757

PubMed

Title	Date	PubMed
Segmental patterns of vestibular-mediated synaptic inputs to axial and limb motoneurons in the neonatal mouse assessed by optical recording.	2010-12-15	20962007
Permeability evaluation through chitosan membranes using taguchi design.	2010-09-25	21179329
Age estimation in 25-45 yrs. old females by physical and radiological methods.	2010-07	21731347
Bicuculline-sensitive primary afferent depolarization remains after greatly restricting synaptic transmission in the mammalian spinal cord.	2010-04-14	20392950
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486
[Acute generalized exanthematous pustulosis induced by topical application of Algipan].	2009-10	19801255
Stability indicating HPLC method for simultaneous determination of mephenesin and diclofenac diethylamine.	2009-01	20177453
Three different types of chirality-driven crystallization within the series of uniformly substituted phenyl glycerol ethers.	2008-11	18767134
Strategy for identification of leachables in packaged pharmaceutical liquid formulations.	2008-02-13	18180126
Comparison of atmospheric pressure photoionization and atmospheric pressure chemical ionization for normal-phase LC/MS chiral analysis of pharmaceuticals.	2007-03-15	17288463
The synthesis of amphipathic prodrugs of 1,2-diol drugs with saccharide conjugates by high regioselective enzymatic protocol.	2007-02-15	17178228
Fatal mephenesin intoxication.	2007-01	17209942
Activity of common anticonvulsant drugs on spinal seizure-induced by sudden cooling.	2006-09-30	16626844
Spinal ventral root after-discharges as a pain index: involvement of NK-1 and NMDA receptors.	2006-04-12	16507302
The role of serendipity in drug discovery.	2006	17117615
Acupuncture therapy rapidly terminates intractable hiccups complicating acute myocardial infarction.	2005-03	15813167
Descending respiratory polysynaptic inputs to cervical and thoracic motoneurons diminish during early postnatal maturation in rat spinal cord.	2005-02	15733100
Simple pharmacological test battery to assess efficacy and side effect profile of centrally acting muscle relaxant drugs.	2004-10-18	16125625
Determination of guaifenesin in human serum by capillary gas chromatography and electron capture detection.	2004-06-29	15193724
Analysis of neutral drugs in human plasma by fluoride attachment in liquid chromatography/negative ion electrospray tandem mass spectrometry.	2004	15329856
DDT-induced tremor in rats: effects of pharmacological agents.	1985	3929313

Patents

Sample Use Guides

In Vivo Use Guide

Oral: 1 to 2 tablets per dose (500 - 1000 mg), 3 times daily Topical: 2 to 3 times a day with area messages of about ten minutes (duration - 5 days).

Route of Administration: Other

In Vitro Use Guide

Mephenesin is oxidatively metabolized in vitro 'by rat and mouse liver slices to 3- (o-tolyloxy)lactic acid. The uMoles of mephenesin metabolized per gram of fresh tissue was apparently a linear relationship with time up to 60 minutes. The maximum percent of substrate oxidized occurred between 1 500- 2000 ug.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:21 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:21 GMT 2025`
Record UNII	7B8PIR2954
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MEPHENESIN

Official Name

English

NSC-25234

Preferred Name

English

MEPHENESIN [MI]

Common Name

English

Mephenesin [WHO-DD]

Common Name

English

MEPHENESIN [MART.]

Common Name

English

TOLSEROL

Code

English

mephenesin [INN]

Common Name

English

3-(O-METHYLPHENOXY)-1,2-PROPANEDIOL

Common Name

English

MEPHENESINE

Common Name

English

Classification Tree Code System Code

WHO-ATC

M03BX06