Carisoprodol (CHEM002508)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2009-07-30 17:58:45 UTC
Update Date2026-03-31 17:11:48 UTC
Accession NumberCHEM002508
Identification
Common NameCarisoprodol
ClassSmall Molecule
DescriptionA centrally acting skeletal muscle relaxant whose mechanism of action is not completely understood but may be related to its sedative actions. It is used as an adjunct in the symptomatic treatment of musculoskeletal conditions associated with painful muscle spasm. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1202)
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Carbamate
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Muscle Relaxant
  • Muscle Relaxant, Central
  • Muscle Relaxant, Skeletal
  • Neuromuscular Agent
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-2-Methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamateChEBI
(1-Methylethyl)carbamic acid 2-(((aminocarbonyl)oxy)methyl)-2-methylpentyl esterChEBI
2-Methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamateChEBI
2-Methyl-2-propyltrimethylene carbamate isopropylcarbamateChEBI
Carbamic acid 2-isopropylcarbamoyloxymethyl-2-methyl-pentyl esterChEBI
CarisoprodolumChEBI
Isopropyl meprobamateChEBI
N-Isopropy-2-methyl-2-propyl-1,3-propanediol dicarbamateChEBI
SomaKegg
(+-)-2-Methyl-2-propyl-1,3-propanediol carbamic acid isopropylcarbamic acidGenerator
(1-Methylethyl)carbamate 2-(((aminocarbonyl)oxy)methyl)-2-methylpentyl esterGenerator
2-Methyl-2-propyl-1,3-propanediol carbamic acid isopropylcarbamic acidGenerator
2-Methyl-2-propyltrimethylene carbamic acid isopropylcarbamic acidGenerator
Carbamate 2-isopropylcarbamoyloxymethyl-2-methyl-pentyl esterGenerator
Isopropyl meprobamic acidGenerator
N-Isopropy-2-methyl-2-propyl-1,3-propanediol dicarbamic acidGenerator
CarisoprodateHMDB
CarisoprodatumHMDB
IsomeprobamateHMDB
IsoprotaneHMDB
IsoprothaneHMDB
IsopropylmeprobamateHMDB
Mio relaxHMDB
Schein brand OF carisoprodolHMDB
SomalgitHMDB
SoprodolHMDB
VanadomHMDB
Wallace brand 1 OF carisoprodolHMDB
Belmac brand OF carisoprodolHMDB
CarisomaHMDB
Forest brand OF carisoprodolHMDB
GM Pharmaceuticals brand OF carisoprodolHMDB
IsobamateHMDB
Carter horner brand OF carisoprodolHMDB
Wallace brand 2 OF carisoprodolHMDB
Wallace brand 3 OF carisoprodolHMDB
Chemical FormulaC12H24N2O4
Average Molecular Mass260.330 g/mol
Monoisotopic Mass260.174 g/mol
CAS Registry Number78-44-4
IUPAC Name2-[(carbamoyloxy)methyl]-2-methylpentyl N-(propan-2-yl)carbamate
Traditional NameSoma
SMILESCCCC(C)(COC(N)=O)COC(=O)NC(C)C
InChI IdentifierInChI=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 KeyOFZCIYFFPZCNJE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as carbamate esters. Carbamate esters are compounds containing an ester of carbamic acid with the general structure R2NC(=O)OR' (R' not H). They are esters of carbamic acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCarbamate esters
Alternative Parents
Substituents
  • Carbamic acid ester
  • Carbonic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point89-91°C
Boiling PointNot Available
Solubility300 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.79 g/LALOGPS
logP1.76ALOGPS
logP1.92ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)15.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area90.65 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity67.1 m³·mol⁻¹ChemAxon
Polarizability28.77 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9200000000-7ee2bc67a583d40d99b8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9200000000-7ee2bc67a583d40d99b8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9320000000-ea5623d29b47a08ec316Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-056r-1920000000-df362ad4c912b7d0fb43Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-4910000000-0fe5eef3c39360c36d38Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ot-9300000000-94d7b1adea0d831c0950Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03dj-9100000000-a99d65f53726ca3b6116Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-9000000000-618eb5a23da29ec51cb6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-9000000000-d2d07fc2a5972fd4e9f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-9000000000-007521fa65c254bad2b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-1920000000-df362ad4c912b7d0fb43Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-03di-9000000000-bf1fe057c44420039b3aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-004i-4910000000-e7f506802140a9e5d5f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-03dj-9100000000-ab0f09b2ddbd1ef81090Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-01ot-9300000000-1ebfa5d842a1f8d54673Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-03di-9000000000-ef44fb81f70af0bfd465Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-03di-9000000000-a7cb3ad99f7b8bfb6ed9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-6490000000-046fd220fa245140ddabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9320000000-b08ca9d93b628ea8b4f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-4f09dfa1c188e3251a65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-9010000000-548142f811b5a3632f8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-37215ebd46867ac40f9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-46650c3ec5dedc27b7ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0lxt-7970000000-bf2aa9b29774479d4c05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6t-9410000000-9352c9b82fc7d1079dd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ec-9100000000-c1581d5627d6283a4fbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0adi-2960000000-0132a40d2da121a22471Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3900000000-5ed690941e48fd4fa317Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-9200000000-84ceb4ca447a62939b63Spectrum
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityCarisoprodol is a central nervous system depressant that acts as a sedative and skeletal muscle relaxant. Rather than acting directly on skeletal muscle, carisoprodol interrupts neuronal communication within the reticular formation and spinal cord, resulting in sedation and alteration in pain perception. Its exact mechanism of action is not yet known.
MetabolismHepatic. Metabolized in the liver via the cytochrome P450 oxidase isozyme CYP2C19. Route of Elimination: Carisoprodol is eliminated by both renal and non-renal routes. Half Life: 8 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the relief of discomfort associated with acute, painful, musculoskeletal conditions.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include drowsiness, giddiness, nausea, indigestion, or rash. Other adverse effects attributed to therapeutic use of carisoprodol include dizziness, irritability, insomnia, diplopia, temporary loss of vision, ataxia, weakness, headache, and dysarthria. Non-CNS adverse effects include gastrointestinal complaints, tachycardia, and postural hypotension. Patients sensitive to sulfites or tartrazine may experience wheezing, allergic rashes including erythema multiforme, or anaphylaxis after using some preparations of carisoprodol which contain such additives
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00395
HMDB IDHMDB0014539
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00032142
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCarisoprodol
Chemspider ID2478
ChEBI ID3419
PubChem Compound ID2576
Kegg Compound IDC07927
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Berger, F.M. and Ludwig, B.J.; U S . Patent 2,937,119; May 17,1960; assigned to Carter
Products, Inc.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14521410
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17725338
3. Littrell RA, Hayes LR, Stillner V: Carisoprodol (Soma): a new and cautious perspective on an old agent. South Med J. 1993 Jul;86(7):753-6.
4. Chou R, Peterson K, Helfand M: Comparative efficacy and safety of skeletal muscle relaxants for spasticity and musculoskeletal conditions: a systematic review. J Pain Symptom Manage. 2004 Aug;28(2):140-75.
5. Toth PP, Urtis J: Commonly used muscle relaxant therapies for acute low back pain: a review of carisoprodol, cyclobenzaprine hydrochloride, and metaxalone. Clin Ther. 2004 Sep;26(9):1355-67.