Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C5H9NO |
| Molecular Weight | 99.1311 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCCC1=O
InChI
InChIKey=SECXISVLQFMRJM-UHFFFAOYSA-N
InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3
| Molecular Formula | C5H9NO |
| Molecular Weight | 99.1311 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Methyl pyrrolidone (or N-methyl pyrrolidone or NMP) is a small molecule acetyl‐lysine mimetic compound with potent immunomodulatory and direct anti‐myeloma activity. NMP is nontoxic, stable and already in use as a solvent in biomedical applications. This compound is under investigation in clinical trial phase I for the treatment of multiple myeloma. The study will evaluate if the NMP can be safely administered to humans at doses, which induce measurable immunological and anti-tumor effects in patients with myeloma. In addition, NMP could be useful for bone fracture repairing. NMP has shown a protective role in osteoblast differentiation in response to hypoxia, and such protection was through inhibiting the NF-κB signaling. Experiments on rodents have revealed that the compound had a remarkable anti-osteoporotic ability preserving activity in the pulp-dentine complex and preventing jawbone loss. These effects made NMP a promising candidate for the preservation of the activity of the pulp-dentin complex and jawbone thickness in post-menopausal females.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| A simple and rapid dispersive liquid-liquid microextraction method followed by GC-FID for determination of N-methylpyrrolidine in cefepime. | 2010-12 |
|
| Validation of capillary electrophoresis method for determination of N-methylpyrrolidine in cefepime for injection. | 2010-11 |
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| Prospective monitoring of cefepime in intensive care unit adult patients. | 2010 |
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| An improved ion chromatographic method for fast and sensitive determination of N-methylpyrrolidine in cefepime hydrochloride. | 2009-08 |
|
| Selective triplet-state formation during charge recombination in a fullerene/Bodipy molecular dyad (Bodipy=borondipyrromethene). | 2009-07-27 |
|
| Using the cationic surfactants N-cetyl-N-methylpyrrolidinium bromide and 1-cetyl-3-methylimidazolium bromide for sweeping-micellar electrokinetic chromatography. | 2009-07-03 |
|
| Embryotoxic potential of N-methyl-pyrrolidone (NMP) and three of its metabolites using the rat whole embryo culture system. | 2009-06-01 |
|
| Pyrrolidinium ionic liquid crystals with pendant mesogenic groups. | 2009-05-19 |
|
| Evaluation of Pharmasolve corneal permeability enhancement and its irritation on rabbit eyes. | 2009-05 |
|
| Formation and properties of stabilized aluminum nanoparticles. | 2009-03 |
|
| 5-(2-Pyrrolidinyl)oxazolidinones and 2-(2-pyrrolidinyl)benzodioxanes: synthesis of all the stereoisomers and alpha4beta2 nicotinic affinity. | 2009-02-01 |
|
| Rapid homogeneous lauroylation of wheat straw hemicelluloses under mild conditions. | 2008-11-24 |
|
| Fiber diffraction as a screen for amyloid inhibitors. | 2008-06 |
|
| Protic ionic liquids based on the dimeric and oligomeric anions: [(AcO)xH(x-1)]-. | 2008-05-28 |
|
| 1-Methyl-1-propyl-pyrrolidinium chloride. | 2008-02-29 |
|
| Evaluation of traps and lures for mass trapping of Mediterranean fruit fly in citrus groves. | 2008-02 |
|
| Preparation of second generation ionic liquids by efficient solvent-free alkylation of N-heterocycles with chloroalkanes. | 2008-01-25 |
|
| 1,1'-Dimethyl-1,1'-(butane-1,4-di-yl)dipyrrolidinium dibromide methanol disolvate. | 2008-01-11 |
|
| Abstracts of papers presented at the 2008 pittsburgh conference. | 2008 |
|
| Nicotine: on the potential role of ionic liquids for its processing and purification. | 2007-07-19 |
|
| Anti-fibrillogenic and fibril-destabilizing activity of nicotine in vitro: implications for the prevention and therapeutics of Lewy body diseases. | 2007-06 |
|
| EPR studies of amine radical cations. Part 2. Thermal and photo-induced rearrangements of propargylamine and allylamine radical cations in low-temperature freon matrices. | 2006-12-28 |
|
| Glyoxalase I-type hemithioacetal isomerization reactivity of a mononuclear Ni(II) deprotonated amide complex. | 2006-12-27 |
|
| A nonradioactive high-throughput/high-content assay for measurement of the human serotonin reuptake transporter function in vitro. | 2006-12 |
|
| Synthetic inhibitors of cytochrome P-450 2A6: inhibitory activity, difference spectra, mechanism of inhibition, and protein cocrystallization. | 2006-11-30 |
|
| Electrokinetic chromatographic characterization of novel pseudo-phases based on N-alkyl-N-methylpyrrolidinium ionic liquid type surfactants. | 2006-11 |
|
| The synthesis of N,O-ferrocenyl pyrrolidine-containing ligands and their application in the diethyl- and diphenylzinc addition to aromatic aldehydes. | 2006-09-29 |
|
| Modeling proline ligation in the heme-dependent CO sensor, CooA, using small-molecule analogs. | 2006-07 |
|
| Influence of endotoxin induced fever on the pharmacokinetics of intramuscularly administered cefepime in rabbits. | 2006-06 |
|
| Direct synthesis of fused 1,2,3,4,5-pentathiepins. | 2005-10-07 |
|
| Synthesis of new, potent avermectin-like insecticidal agents. | 2005-07-04 |
|
| Molecular dissection of tropisetron, an alpha7 nicotinic acetylcholine receptor-selective partial agonist. | 2005-04-22 |
|
| 5-substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6. | 2005-01-13 |
|
| Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. | 2004-02-15 |
|
| A new class of potent non-imidazole H(3) antagonists: 2-aminoethylbenzofurans. | 2004-02-09 |
|
| Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride. | 2004-01-19 |
|
| A simple and sensitive GC method for determination of N-methylpyrrolidine in cefepime and its preparation. | 2003-11-24 |
|
| Physicochemical determinants for drug induced blockade of HERG potassium channels: effect of charge and charge shielding. | 2003-10 |
|
| N-n-alkylpyridinium analogs, a novel class of nicotinic receptor antagonists: selective inhibition of nicotine-evoked [3H] dopamine overflow from superfused rat striatal slices. | 2003-09 |
|
| Kinetics and mechanism of ring transformation of S-[1-(4-methoxyphenyl)pyrrolidin-2-on-3-yl]isothiuronium bromide to 2-methylimino-5-[2-(4-methoxyphenylamino)ethyl]thiazolidin-4-one. | 2003-04-07 |
|
| N-methylpiperidinemethyl, N-methylpyrrolidyl and N-methylpyrrolidinemethyl esters as PET radiotracers for acetylcholinesterase activity. | 2003-04 |
|
| A new highly asymmetric chelation-controlled heck arylation. | 2003-03-26 |
|
| Nicotine breaks down preformed Alzheimer's beta-amyloid fibrils in vitro. | 2002-11-01 |
|
| Acetylation of rice straw with or without catalysts and its characterization as a natural sorbent in oil spill cleanup. | 2002-10-23 |
|
| Some aspects of NaBH(4) reduction in NMP. | 2002-08 |
|
| A comparative analysis of glove permeation resistance to paint stripping formulations. | 2002-02-15 |
|
| Studies on a soft glycopyrrolate analog, SG-1. | 2002-02 |
|
| O-Phosphonatomethylcholine, its analogues, alkyl esters, and their biological activity. | 2001-12-06 |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02468687
N-methyl-pyrrolidone will be taken each morning as a single daily dose of oral suspension at a concentration of 50mg/ml on an empty stomach at least 30 minutes prior to food.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 17:49:32 GMT 2025
by
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on
Mon Mar 31 17:49:32 GMT 2025
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| Record UNII |
JR9CE63FPM
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| Record Status |
Validated (UNII)
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N-METHYL-2-PYRROLIDONE
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DTXSID6020856
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m7460
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7307
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C45678
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CONCEPT | Industrial Aid | ||
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