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

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 sensitive GC method for determination of N-methylpyrrolidine in cefepime and its preparation.
2003 Nov 24
Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6.
2004 Feb 15
Glyoxalase I-type hemithioacetal isomerization reactivity of a mononuclear Ni(II) deprotonated amide complex.
2006 Dec 27
Synthetic inhibitors of cytochrome P-450 2A6: inhibitory activity, difference spectra, mechanism of inhibition, and protein cocrystallization.
2006 Nov 30
1-Methyl-1-propyl-pyrrolidinium chloride.
2008 Feb 29
1,1'-Dimethyl-1,1'-(butane-1,4-di-yl)dipyrrolidinium dibromide methanol disolvate.
2008 Jan 11
Protic ionic liquids based on the dimeric and oligomeric anions: [(AcO)xH(x-1)]-.
2008 May 28
Rapid homogeneous lauroylation of wheat straw hemicelluloses under mild conditions.
2008 Nov 24
An improved ion chromatographic method for fast and sensitive determination of N-methylpyrrolidine in cefepime hydrochloride.
2009 Aug
Selective triplet-state formation during charge recombination in a fullerene/Bodipy molecular dyad (Bodipy=borondipyrromethene).
2009 Jul 27
Using the cationic surfactants N-cetyl-N-methylpyrrolidinium bromide and 1-cetyl-3-methylimidazolium bromide for sweeping-micellar electrokinetic chromatography.
2009 Jul 3
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
Evaluation of Pharmasolve corneal permeability enhancement and its irritation on rabbit eyes.
2009 May
Pyrrolidinium ionic liquid crystals with pendant mesogenic groups.
2009 May 19
Prospective monitoring of cefepime in intensive care unit adult patients.
2010
A simple and rapid dispersive liquid-liquid microextraction method followed by GC-FID for determination of N-methylpyrrolidine in cefepime.
2010 Dec
Validation of capillary electrophoresis method for determination of N-methylpyrrolidine in cefepime for injection.
2010 Nov
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 Fri Dec 15 15:11:25 UTC 2023
Edited
by admin
on Fri Dec 15 15:11:25 UTC 2023
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
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 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
CAS
872-50-4
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
RXCUI
1305552
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY RxNorm
EVMPD
SUB37598
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
FDA UNII
JR9CE63FPM
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
RS_ITEM_NUM
1601703
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
DAILYMED
JR9CE63FPM
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
PUBCHEM
13387
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
RS_ITEM_NUM
1437202
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
ALTERNATIVE
ECHA (EC/EINECS)
212-828-1
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
CAS
51013-18-4
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
NON-SPECIFIC SUBSTITUTION
SMS_ID
100000129174
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
WIKIPEDIA
N-METHYL-2-PYRROLIDONE
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID6020856
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
NCI_THESAURUS
C77542
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
DRUG BANK
DB12521
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
MESH
C038678
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
MERCK INDEX
m7460
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY Merck Index
CHEBI
7307
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
CONCEPT Industrial Aid
NSC
4594
Created by admin on Fri Dec 15 15:11:25 UTC 2023 , Edited by admin on Fri Dec 15 15:11:25 UTC 2023
PRIMARY