Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110619
Identification
Name: carbamate
Description:Carbamic acid is occasionally found as carbamate in workers exposed to pesticides. Carbamates, particularly carbofuran, seem to be more associated with exuberant and diversified symptomatology of pesticide exposure than organophosphates. Neurological symptoms occur among farmers occupationally exposed to acetylcholinesterase-inhibiting insecticides such as carbamates. Carbamic acid products of several amines, such as beta-N-methylamino-L-alanine (BMAA), ethylenediamine, and L-cysteine have been implicated in toxicity. Studies suggested that a significant portion of amino-compounds in biological samples (that naturally contain CO2/bicarbonate) can be present as a carbamic acid. The formation of carbamate glucuronide metabolites has been described for numerous pharmaceuticals and they have been identified in all of the species commonly used in drug metabolism studies (rat, dog, mouse, rabbit, guinea pig, and human). There has been no obvious species specificity for their formation and no preference for 1 or 2 degree amines. Many biological reactions have also been described in the literature that involve the reaction of CO2 with amino groups of biomolecules. For example, CO2 generated from cellular respiration is expired in part through the reversible formation of a carbamate between CO2 and the -amino groups of the alpha and beta-chains of hemoglobin. Glucuronidation is an important mechanism used by mammalian systems to clear and eliminate both endogenous and foreign chemicals. Many functional groups are susceptible to conjugation with glucuronic acid, including hydroxyls, phenols, carboxyls, activated carbons, thiols, amines, and selenium. Primary and secondary amines can also react with carbon dioxide (CO2) via a reversible reaction to form a carbamic acid. The carbamic acid is also a substrate for glucuronidation and results in a stable carbamate glucuronide metabolite. The detection and characterization of these products has been facilitated greatly by the advent of soft ionization mass spectrometry techniques and high field NMR instrumentation. (PMID: 16268118 , 17168688 , 12929145 ).
Structure
Thumb
Synonyms:
  • carbamic acid
  • aminoformic acid
Chemical Formula: CH2NO2
Average Molecular Weight: 60.032
Monoisotopic Molecular Weight: 61.0163783457
InChI Key: KXDHJXZQYSOELW-UHFFFAOYSA-M
InChI: InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4)/p-1
CAS number: 463-77-4
IUPAC Name:carbamate
Traditional IUPAC Name: carbamic acid
SMILES:C(=O)([O-])N
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as carbamic acids. These are compounds containing the carbamic acid functional group, with the general structure RN(R')C(=O)OH or RN(R')C(=O)[O-] where R,R' = H or organyl group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct Parent Carbamic acids
Alternative Parents
Substituents
  • Carbamic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility379.0 mg/mLALOGPS
logP-1.1ALOGPS
logP-0.56ChemAxon
logS0.79ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity11.32 m3·mol-1ChemAxon
Polarizability4.68 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-33c2cd9e9f87e70aeee7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-80dc946b5f814bf962fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-db68c8dff28932d0bd97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-9000000000-54e827d7f4201ae683bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-9000000000-3158c8b265d264989bd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-24350f23db0893ec042cView in MoNA
References
References:
  • Rendon von Osten J, Epomex C, Tinoco-Ojanguren R, Soares AM, Guilhermino L: Effect of pesticide exposure on acetylcholinesterase activity in subsistence farmers from Campeche, Mexico. Arch Environ Health. 2004 Aug;59(8):418-25. [16268118 ]
  • Schaefer WH: Reaction of primary and secondary amines to form carbamic acid glucuronides. Curr Drug Metab. 2006 Dec;7(8):873-81. [17168688 ]
  • Smit LA, van-Wendel-de-Joode BN, Heederik D, Peiris-John RJ, van der Hoek W: Neurological symptoms among Sri Lankan farmers occupationally exposed to acetylcholinesterase-inhibiting insecticides. Am J Ind Med. 2003 Sep;44(3):254-64. [12929145 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
ChEBI13941
ChemSpider270
HMDBHMDB03551
KEGGC01563
PubChem276