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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
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
O-Phosphonatomethylcholine, its analogues, alkyl esters, and their biological activity.
2001 Dec 6
Studies on a soft glycopyrrolate analog, SG-1.
2002 Feb
Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6.
2004 Feb 15
A new class of potent non-imidazole H(3) antagonists: 2-aminoethylbenzofurans.
2004 Feb 9
Direct synthesis of fused 1,2,3,4,5-pentathiepins.
2005 Oct 7
Influence of endotoxin induced fever on the pharmacokinetics of intramuscularly administered cefepime in rabbits.
2006 Jun
Nicotine: on the potential role of ionic liquids for its processing and purification.
2007 Jul 19
Evaluation of traps and lures for mass trapping of Mediterranean fruit fly in citrus groves.
2008 Feb
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
Preparation of second generation ionic liquids by efficient solvent-free alkylation of N-heterocycles with chloroalkanes.
2008 Jan 25
Prospective monitoring of cefepime in intensive care unit adult patients.
2010
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