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
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 |
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Some aspects of NaBH(4) reduction in NMP. | 2002 Aug |
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Studies on a soft glycopyrrolate analog, SG-1. | 2002 Feb |
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A comparative analysis of glove permeation resistance to paint stripping formulations. | 2002 Jan-Feb |
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Nicotine breaks down preformed Alzheimer's beta-amyloid fibrils in vitro. | 2002 Nov 1 |
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Acetylation of rice straw with or without catalysts and its characterization as a natural sorbent in oil spill cleanup. | 2002 Oct 23 |
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N-methylpiperidinemethyl, N-methylpyrrolidyl and N-methylpyrrolidinemethyl esters as PET radiotracers for acetylcholinesterase activity. | 2003 Apr |
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A new highly asymmetric chelation-controlled heck arylation. | 2003 Mar 26 |
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Physicochemical determinants for drug induced blockade of HERG potassium channels: effect of charge and charge shielding. | 2003 Oct |
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Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. | 2004 Feb 15 |
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Molecular dissection of tropisetron, an alpha7 nicotinic acetylcholine receptor-selective partial agonist. | 2005 Apr 22 |
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5-substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6. | 2005 Jan 13 |
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Modeling proline ligation in the heme-dependent CO sensor, CooA, using small-molecule analogs. | 2006 Jul |
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Electrokinetic chromatographic characterization of novel pseudo-phases based on N-alkyl-N-methylpyrrolidinium ionic liquid type surfactants. | 2006 Nov |
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The synthesis of N,O-ferrocenyl pyrrolidine-containing ligands and their application in the diethyl- and diphenylzinc addition to aromatic aldehydes. | 2006 Sep 29 |
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Rapid homogeneous lauroylation of wheat straw hemicelluloses under mild conditions. | 2008 Nov 24 |
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Embryotoxic potential of N-methyl-pyrrolidone (NMP) and three of its metabolites using the rat whole embryo culture system. | 2009 Jun 1 |
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Formation and properties of stabilized aluminum nanoparticles. | 2009 Mar |
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A simple and rapid dispersive liquid-liquid microextraction method followed by GC-FID for determination of N-methylpyrrolidine in cefepime. | 2010 Dec |
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
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C45678
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SUBSTANCE RECORD