U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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
Some aspects of NaBH(4) reduction in NMP.
2002 Aug
Studies on a soft glycopyrrolate analog, SG-1.
2002 Feb
A comparative analysis of glove permeation resistance to paint stripping formulations.
2002 Jan-Feb
Nicotine breaks down preformed Alzheimer's beta-amyloid fibrils in vitro.
2002 Nov 1
Acetylation of rice straw with or without catalysts and its characterization as a natural sorbent in oil spill cleanup.
2002 Oct 23
N-methylpiperidinemethyl, N-methylpyrrolidyl and N-methylpyrrolidinemethyl esters as PET radiotracers for acetylcholinesterase activity.
2003 Apr
A new highly asymmetric chelation-controlled heck arylation.
2003 Mar 26
Physicochemical determinants for drug induced blockade of HERG potassium channels: effect of charge and charge shielding.
2003 Oct
Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6.
2004 Feb 15
Molecular dissection of tropisetron, an alpha7 nicotinic acetylcholine receptor-selective partial agonist.
2005 Apr 22
5-substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6.
2005 Jan 13
Modeling proline ligation in the heme-dependent CO sensor, CooA, using small-molecule analogs.
2006 Jul
Electrokinetic chromatographic characterization of novel pseudo-phases based on N-alkyl-N-methylpyrrolidinium ionic liquid type surfactants.
2006 Nov
The synthesis of N,O-ferrocenyl pyrrolidine-containing ligands and their application in the diethyl- and diphenylzinc addition to aromatic aldehydes.
2006 Sep 29
Rapid homogeneous lauroylation of wheat straw hemicelluloses under mild conditions.
2008 Nov 24
Embryotoxic potential of N-methyl-pyrrolidone (NMP) and three of its metabolites using the rat whole embryo culture system.
2009 Jun 1
Formation and properties of stabilized aluminum nanoparticles.
2009 Mar
A simple and rapid dispersive liquid-liquid microextraction method followed by GC-FID for determination of N-methylpyrrolidine in cefepime.
2010 Dec
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
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
METHYL PYRROLIDONE [INCI]
Common 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 Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
CAS
872-50-4
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
RXCUI
1305552
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY RxNorm
EVMPD
SUB37598
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
FDA UNII
JR9CE63FPM
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
RS_ITEM_NUM
1601703
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
DAILYMED
JR9CE63FPM
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
PUBCHEM
13387
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
RS_ITEM_NUM
1437202
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
ALTERNATIVE
ECHA (EC/EINECS)
212-828-1
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
CAS
51013-18-4
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
NON-SPECIFIC SUBSTITUTION
SMS_ID
100000129174
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
WIKIPEDIA
N-METHYL-2-PYRROLIDONE
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID6020856
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
NCI_THESAURUS
C77542
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
DRUG BANK
DB12521
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
MESH
C038678
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
MERCK INDEX
m7460
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY Merck Index
CHEBI
7307
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
CONCEPT Industrial Aid
NSC
4594
Created by admin on Fri Dec 15 15:11:25 GMT 2023 , Edited by admin on Fri Dec 15 15:11:25 GMT 2023
PRIMARY