C8759

Sigma-Aldrich

Carisoprodol

Synonym(s):
2-Methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamate
Empirical Formula (Hill Notation):
C12H24N2O4
CAS Number:
Molecular Weight:
260.33
EC Number:
MDL number:
PubChem Substance ID:

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C8759.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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...
Laxmaiah Manchikanti et al.
Pain physician, 16(1), E1-E13 (2013-01-24)
Reports of chronic pain and associated opioid use, abuse, and fatalities continue to increase at an alarming rate, not only in the United States but also across the globe. In light of the many resultant fatalities, multiple authors and authorities...
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...
Jennifer A Fass
The Annals of pharmacotherapy, 44(12), 1962-1967 (2010-11-11)
To review the current legal status and patterns of abuse of carisoprodol. A literature search was conducted through MEDLINE (1950-August 2010), PubMed (1966-August 2010), EMBASE (1966-August 2010), and International Pharmaceutical Abstracts (1970-August 2010) using the search terms carisoprodol and abuse....
B K Logan et al.
Journal of forensic sciences, 45(3), 619-623 (2000-06-16)
This paper considers the pharmacology of the centrally acting muscle relaxant carisoprodol, and its metabolite meprobamate, which is also administered as an anxiolytic in its own right. Literature implicating these drugs in impaired driving is also reviewed. A series of...

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