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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
Structure of Methylpyrrolidone

SMILES

CN1CCCC1=O

InChI

InChIKey=SECXISVLQFMRJM-UHFFFAOYSA-N
InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
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
Prospective monitoring of cefepime in intensive care unit adult patients.
2010
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
Patents

Sample Use Guides

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
by admin
on Mon Mar 31 17:49:32 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:32 GMT 2025
Record UNII
JR9CE63FPM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Methylpyrrolidone
NF   USP-RS  
Common Name English
METHYL PYRROLIDONE
II   INCI  
INCI  
Preferred Name English
N-METHYLPYRROLIDONE
EP   MART.  
Systematic Name English
N-METHYL-PYRROLIDONE
Systematic Name English
1-METHYL-2-PYRROLIDINONE
HSDB  
Systematic Name English
2-PYRROLIDINONE, METHYL-
Systematic Name English
N-METHYLPYRROLIDONE [MART.]
Common Name English
N-METHYLPYRROLIDONE [USP-RS]
Common Name English
NSC-4594
Code English
1-METHYLPYRROLIDONE [MI]
Common Name English
1-METHYLPYRROLIDINONE
Systematic Name English
1-METHYL-2-PYRROLIDONE
Systematic Name English
1-METHYL-5-PYRROLIDINONE
Systematic Name English
N-methyl-2-pyrrolidinone
Systematic Name English
N-Methyl-2-pyrrolidone
Systematic Name English
N-METHYLPYRROLIDONE [EP MONOGRAPH]
Common Name English
METHYL PYRROLIDONE [II]
Common Name English
1-METHYL-2-PYRROLIDINONE [HSDB]
Common Name English
NMP
Common Name English
1-METHYLPYRROLIDONE
Systematic Name English
METHYLPYRROLIDONE [USP-RS]
Common Name English
METHYLPYRROLIDONE [NF]
Common Name English
Code System Code Type Description
HSDB
5022
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY
CAS
872-50-4
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY
RXCUI
1305552
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PRIMARY RxNorm
EVMPD
SUB37598
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PRIMARY
FDA UNII
JR9CE63FPM
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY
RS_ITEM_NUM
1601703
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PRIMARY
DAILYMED
JR9CE63FPM
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY
PUBCHEM
13387
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY
RS_ITEM_NUM
1437202
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
ALTERNATIVE
ECHA (EC/EINECS)
212-828-1
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY
CAS
51013-18-4
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
NON-SPECIFIC SUBSTITUTION
SMS_ID
100000129174
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY
WIKIPEDIA
N-METHYL-2-PYRROLIDONE
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID6020856
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY
NCI_THESAURUS
C77542
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY
DRUG BANK
DB12521
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY
MESH
C038678
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY
MERCK INDEX
m7460
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY Merck Index
CHEBI
7307
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
CONCEPT Industrial Aid
NSC
4594
Created by admin on Mon Mar 31 17:49:32 GMT 2025 , Edited by admin on Mon Mar 31 17:49:32 GMT 2025
PRIMARY