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C8759

Sigma-Aldrich

Carisoprodol

Synonym(s):

2-Methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamate

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About This Item

Empirical Formula (Hill Notation):
C12H24N2O4
CAS Number:
78-44-4
Molecular Weight:
260.33
EC Number:
201-118-7
MDL number:
MFCD00057661
UNSPSC Code:
12352200
PubChem Substance ID:
24278083

drug control

USDEA Schedule IV

solubility

ethanol: soluble

originator

Schering Plough

storage temp.

2-8°C

SMILES string

CCCC(C)(COC(N)=O)COC(=O)NC(C)C

InChI

1S/C12H24N2O4/c1-5-6-12(4,7-17-10(13)15)8-18-11(16)14-9(2)3/h9H,5-8H2,1-4H3,(H2,13,15)(H,14,16)

InChI key

OFZCIYFFPZCNJE-UHFFFAOYSA-N

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General description

Carisoprodol (N-isopropyl-2-methyl-2-propyl-l,3-propanediol dicarbamate) is a dicarbamate that is structurally similar to mephenesin and meprobamate. It functions as a skeletal muscle relaxant and has analgesic properties. Although it does not have an effect on behavior, it inhibits reticular formation. The area associated with pain perception in the CNS is affected by carisoprodol for its analgesic activity.
Carisoprodol is actively metabolized to meprobamate, a depressant of the CNS having sedative hypnotic.

Application

Carisoprodol has been used as a standard for quantitative determination of carisoprodol in tablets using high-performance thin-layer chromatography. It has also been used to study the effect of pharmacological agents on the muscles of dystrophin-deficient mdx5Cv mice.

Biochem/physiol Actions

Metabolite of meprobamate that is a skeletal muscle relaxant, reduces muscle spasm by depression of brainstem neurons.

Features and Benefits

This compound was developed by Schering Plough. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Analysis of carisoprodol tablets by HPTLC with visible absorbance densitometry.
Fisher, J., and J. Sherma
Acta Chromatographica , 96-101 (2001)
Michael B Gatch et al.
Drug and alcohol dependence, 123(1-3), 29-34 (2011-11-08)
Carisoprodol is a muscle relaxant that acts at the GABA(A) receptor. Concerns about the abuse liability of carisoprodol are increasing, but evidence that carisoprodol produces tolerance and a significant withdrawal syndrome has yet to be established. The purpose of the
James P Zacny et al.
Pharmacology, biochemistry, and behavior, 100(1), 138-143 (2011-09-03)
Carisoprodol is a centrally acting drug used to relieve skeletal muscle spasms and associated pain in acute musculoskeletal conditions. There is evidence from different sources that this oral muscle relaxant is abused and that it is associated with impairment leading
J G Bramness et al.
Clinical pharmacology and therapeutics, 91(3), 438-441 (2012-02-10)
Carisoprodol, a centrally acting muscle relaxant indicated for acute lower back pain, has been available in Europe and the United States since 1959. Studies indicating increased risk of abuse or addiction led to withdrawal of the drug from the market
James P Zacny et al.
Drug and alcohol dependence, 120(1-3), 229-232 (2011-08-16)
Some chronic pain patients on long-term opioid therapy also take centrally active skeletal muscle relaxants. One of those muscle relaxants is carisoprodol, a drug that is abused and capable of producing impairment. It would be of relevance to characterize the
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