1-Methyl-2-pyrrolidone (CHEM003902)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2014-09-17 20:01:58 UTC
Update Date2016-11-09 01:09:14 UTC
Accession NumberCHEM003902
Identification
Common Name1-Methyl-2-pyrrolidone
ClassSmall Molecule
Description1-Methyl-2-pyrrolidone, or N-Methyl-2-pyrrolidone (NMP), is a chemical compound with 5-membered lactam structure. It is a colorless to slightly yellow liquid miscible with water. It is used in petrochemical processing, and as a solvent for surface treatment of textiles, resins and metal coated plastics or as a paint stripper. In the pharmaceutical industry, N-methyl-2-pyrrolidone is used in the formulation for drugs by both oral and transdermal delivery routes. NMP has been identified as a reproductive toxicant, first by California in 2001[3] and then by the European Commission in 2003. In the face of increasing regulation, some manufacturers are considering alternative solvents for some applications, especially where worker exposure is difficult to control, such as in paint stripping, graffiti removal, and agriculture. (Wikipedia)
Contaminant Sources
  • Clean Air Act Chemicals
  • ECHA Toxic for reproduction
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-Methyl-2-pyrrolidinoneChEBI
1-Methylazacyclopentan-2-oneChEBI
N-Methyl-2-pyrrolidinoneChEBI
N-Methyl-alpha-pyrrolidinoneChEBI
N-Methyl-alpha-pyrrolidoneChEBI
N-Methyl-gamma-butyrolactamChEBI
NMPChEBI
N-MethylpyrrolidoneKegg
N-Methyl-a-pyrrolidinoneGenerator
N-Methyl-α-pyrrolidinoneGenerator
N-Methyl-a-pyrrolidoneGenerator
N-Methyl-α-pyrrolidoneGenerator
N-Methyl-g-butyrolactamGenerator
N-Methyl-γ-butyrolactamGenerator
1-Methyl-2-pyrrolidinone, 2,3,4,5-(14)C-labeledMeSH
N-MethylpyrrolidinoneMeSH
1-Methyl-2-pyrrolidinone, 1-methyl-(14)C-labeledMeSH
PharmasolveMeSH
N-Methyl-2-pyrrolidoneMeSH
Methyl pyrrolidoneMeSH
Chemical FormulaC5H9NO
Average Molecular Mass99.131 g/mol
Monoisotopic Mass99.068 g/mol
CAS Registry Number872-50-4
IUPAC Name1-methylpyrrolidin-2-one
Traditional Namemethylpyrrolidone
SMILESCN1CCCC1=O
InChI IdentifierInChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3
InChI KeySECXISVLQFMRJM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassN-alkylpyrrolidines
Direct ParentN-alkylpyrrolidines
Alternative Parents
Substituents
  • Pyrrolidone
  • 2-pyrrolidone
  • N-alkylpyrrolidine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Microsome
  • Microtubule
  • Mitochondrion
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
QuinolonesNot AvailableNot Available
ApoptosisNot Availablemap04210
Nicotine addictionNot Availablemap05033
Mismatch repairNot Availablemap03430
Cell cycleNot Availablemap04110
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless to slightly yellow liquid.
Experimental Properties
PropertyValue
Melting Point-24°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility853 g/LALOGPS
logP-0.72ALOGPS
logP-0.36ChemAxon
logS0.93ALOGPS
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity27.15 m³·mol⁻¹ChemAxon
Polarizability10.7 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-9000000000-f6b5ec5cf179d5b2b4e3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0005-9000000000-47ce7569060cdb946f8cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-b144630f86d4b8e66518Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-374f2f08e213ac620908Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0zfr-8900000000-49455aab0a6c37691a02Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-db81a1cd9771bdf5636cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-d604c3fdefd449d36b13Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0900000000-dabd1db3f0942df68f1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-ce64e8af2b11f9d10358Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3900000000-994475260f0994c425c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9000000000-84a641fdb9dbe809d098Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-900ff8933c879631d09dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-cd5028e268ba08ceadb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-7f6caecde6fc71b63720Spectrum
MSMass Spectrum (Electron Ionization)splash10-0007-9000000000-6f78d4926f0506c5f52fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
Metabolism1-Methyl-2-pyrrolidone is rapidly biotransformed by hydroxylation to 5-hydroxy- N -methyl-2-pyrrolidone, which is further oxidized to N -methylsuccinimide; this intermediate is further hydroxylated to 2-hydroxy- N - methylsuccinimide. These metabolites are all colourless. The excreted amounts of NMP metabolites in the urine after inhalation or oral intake represented about 100% and 65% of the administered doses, respectively.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources1-Methyl-2-pyrrolidone is used in petrochemical processing, and as a solvent for surface treatment of textiles, resins and metal coated plastics or as a paint stripper. In the pharmaceutical industry, N-methyl-2-pyrrolidone is used in the formulation for drugs by both oral and transdermal delivery routes.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsRapid, irregular respiration, shortnessof breath, decreased pain reflex, and slight bloody nasalsecretion.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB12521
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00039855
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkN-Methyl-2-pyrrolidone
Chemspider IDNot Available
ChEBI ID7307
PubChem Compound ID13387
Kegg Compound IDC11118
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23337464
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24446970