1-Methyl-2-pyrrolidone (T3D4946)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-09-17 20:01:58 UTC
Update Date2014-12-24 20:27:00 UTC
Accession NumberT3D4946
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)
Compound Type
  • Amide
  • Amine
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
1-Methyl-2-pyrrolidinone
1-Methylazacyclopentan-2-one
N-Methyl-alpha-pyrrolidinone
N-Methyl-alpha-pyrrolidone
N-Methyl-gamma-butyrolactam
NMP
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 KeyInChIKey=SECXISVLQFMRJM-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
LogPNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-9000000000-f6b5ec5cf179d5b2b4e32017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0005-9000000000-47ce7569060cdb946f8c2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-b144630f86d4b8e665182017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-374f2f08e213ac6209082017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0zfr-8900000000-49455aab0a6c37691a022017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-db81a1cd9771bdf5636c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-d604c3fdefd449d36b132017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0900000000-dabd1db3f0942df68f1f2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-ce64e8af2b11f9d103582016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3900000000-994475260f0994c425c92016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9000000000-84a641fdb9dbe809d0982016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-900ff8933c879631d09d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-cd5028e268ba08ceadb22016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-7f6caecde6fc71b637202016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0007-9000000000-6f78d4926f0506c5f52f2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound IDNot Available
ChEMBL IDCHEMBL12543
ChemSpider ID12814
KEGG ID13387
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4946.pdf
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Aromatase
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.18 uMTox21_Aromatase_InhibitionTox21/NCGC
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]