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Chemical Compound Review

M-Pyrol     1-methylpyrrolidin-2-one

Synonyms: SureCN487, M-PYROL(TM), PubChem17618, CHEMBL12543, NSC-4594, ...
 
 
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Disease relevance of Methylpyrrolidone

 

High impact information on Methylpyrrolidone

  • Analyses of several sulfoxide complexes including rac-11 with N,N-dimethylacetamide (DMAC) or N-methyl-2-pyrrolidone (NMP) in a MeOH solution utilizing cold-spray ionization mass spectrometry provided, for the first time, direct information for intermolecular nonbonded S...O interactions between sulfoxides and amide (or lactam) in a solution [6].
  • Addition of 1.0% (vol/vol) of permeation enhancer, such as oleic acid or N-methyl-2-pyrrolidone, to the ethanol/tricaprylin (50:50) cosolvent system could not significantly increase the permeation rate of ddC [7].
  • Acylation of the amino group on the aromatic ring with acid chlorides in N-methylpyrrolidone (no DMF, no base!) followed by cleavage from the resin using TFA/Me(2)S/water (90:5:5) provides the acylated benzodiazepinones in 52-69% (PS resin) and 41-48% (TG resin) yield (based on the theoretical loading) and >70% purity (HPLC, 210 nm) [8].
  • MGBG penetration in saline, Vehicle N, decylmethylsulfoxide, and N-methylpyrrolidone was determined in normal human skin in vitro [9].
  • The Sonogashira reaction of bromofluoro-substituted alkenes with terminal alkynes, followed by base-catalyzed cyclization in refluxing N-methyl-2-pyrrolidinone (NMP), affords the corresponding fluorinated naphthalene and phenanthrene derivatives in good yields [10].
 

Chemical compound and disease context of Methylpyrrolidone

  • To establish a guideline for residual solvents in medicine, the permitted daily exposure (PDE), equivalent to TDI, of N,N-dimethylformamide was derived on the basis of developmental toxicity (malformation) and of N-methylpyrrolidone on the basis of the developmental neurotoxicity [11].
 

Biological context of Methylpyrrolidone

 

Anatomical context of Methylpyrrolidone

 

Associations of Methylpyrrolidone with other chemical compounds

 

Gene context of Methylpyrrolidone

 

Analytical, diagnostic and therapeutic context of Methylpyrrolidone

References

  1. 1-Methyl-2-pyrrolidinone (NMP) does not induce structural and numerical chromosomal aberrations in vivo. Engelhardt, G., Fleig, H. Mutat. Res. (1993) [Pubmed]
  2. Developmental toxicity of N-methyl-2-pyrrolidone administered orally to rats. Saillenfait, A.M., Gallissot, F., Langonné, I., Sabaté, J.P. Food Chem. Toxicol. (2002) [Pubmed]
  3. Subchronic feeding study in beagle dogs of N-methylpyrrolidone. Becci, P.J., Gephart, L.A., Koschier, F.J., Johnson, W.D., Burnette, L.W. Journal of applied toxicology : JAT. (1983) [Pubmed]
  4. Physicochemical investigations of dipolar aprotic solvents as potential cholelitholytic agents. Kennelly, P., Corrigan, O.I. J. Pharm. Pharmacol. (1987) [Pubmed]
  5. The thermoregulatory mechanism of melatonin-induced hypothermia in chicken. Rozenboim, I., Miara, L., Wolfenson, D. Am. J. Physiol. (1998) [Pubmed]
  6. Highly stereoselective asymmetric pummerer reactions that incorporate intermolecular and intramolecular nonbonded S...O interactions. Nagao, Y., Miyamoto, S., Miyamoto, M., Takeshige, H., Hayashi, K., Sano, S., Shiro, M., Yamaguchi, K., Sei, Y. J. Am. Chem. Soc. (2006) [Pubmed]
  7. Transdermal delivery of zalcitabine: in vitro skin permeation study. Kim, D.D., Chien, Y.W. AIDS (1995) [Pubmed]
  8. Solid-phase synthesis of 7-acylamino-1,4-benzodiazepine-2,5-diones. Ettmayer, P., Chloupek, S., Weigand, K. Journal of combinatorial chemistry. (2003) [Pubmed]
  9. Percutaneous penetration of methylglyoxal bis(guanylhydrazone): effects on hairless mouse epidermis in vivo. McCullough, J.L., Weinstein, G.D., Rosenblum, M.G., Jenkins, J.J. J. Invest. Dermatol. (1983) [Pubmed]
  10. A simple, two-step, site-specific preparation of fluorinated naphthalene and phenanthrene derivatives from fluorobromo-substituted alkenes. Wang, Y., Xu, J., Burton, D.J. J. Org. Chem. (2006) [Pubmed]
  11. Principles of risk assessment for determining the safety of chemicals: recent assessment of residual solvents in drugs and di(2-ethylhexyl) phthalate. Hasegawa, R., Koizumi, M., Hirose, A. Congenital anomalies. (2004) [Pubmed]
  12. Site-specific preparation of 3-fluoro-1-substituted-naphthalenes via a novel base-catalyzed cyclization reaction from (E)-monofluoroenynes. Xu, J., Wang, Y., Burton, D.J. Org. Lett. (2006) [Pubmed]
  13. A new, efficient glycosylation method for oligosaccharide synthesis under neutral conditions: preparation and use of new DISAL donors. Petersen, L., Jensen, K.J. J. Org. Chem. (2001) [Pubmed]
  14. Effects of prenatal exposure to N-methylpyrrolidone on postnatal development and behavior in rats. Hass, U., Lund, S.P., Elsner, J. Neurotoxicology and teratology. (1994) [Pubmed]
  15. N-methyl-2-pyrrolidone as a cosolvent: relationship of cosolvent effect with solute polarity and the presence of proton-donating groups on model drug compounds. Tarantino, R., Bishop, E., Chen, F.C., Iqbal, K., Malick, A.W. Journal of pharmaceutical sciences. (1994) [Pubmed]
  16. Poly(lactic-co-glycolic acid) hollow fibre membranes for use as a tissue engineering scaffold. Ellis, M.J., Chaudhuri, J.B. Biotechnol. Bioeng. (2007) [Pubmed]
  17. Osteoconduction exerted by methylpyrrolidinone chitosan used in dental surgery. Muzzarelli, R.A., Biagini, G., Bellardini, M., Simonelli, L., Castaldini, C., Fratto, G. Biomaterials (1993) [Pubmed]
  18. Contribution of CYP2E1 to N-methyl-2-pyrrolidone metabolism. Ligocka, D., Lison, D., Haufroid, V. Arch. Toxicol. (2003) [Pubmed]
  19. Adrenalin release caused by N-methylpyrrolidone injected into the adrenal gland. Baggio, G., Ferrari, F., Ferrari, P. Il Farmaco; edizione pratica. (1976) [Pubmed]
  20. Osteoconductive properties of methylpyrrolidinone chitosan in an animal model. Muzzarelli, R.A., Zucchini, C., Ilari, P., Pugnaloni, A., Mattioli Belmonte, M., Biagini, G., Castaldini, C. Biomaterials (1993) [Pubmed]
  21. Gel filtration of protected peptides on Enzacryl K2 in dimethylformamide and N-methyl-2-pyrrolidone. Galpin, I.J., Handa, B.K., Moore, S., Ramage, R. J. Chromatogr. (1976) [Pubmed]
  22. Transdermal delivery of dideoxynucleoside-type anti-HIV drugs. 2. The effect of vehicle and enhancer on skin permeation. Kim, D.D., Chien, Y.W. Journal of pharmaceutical sciences. (1996) [Pubmed]
  23. Studies of in vitro skin permeation and retention of a leukotriene antagonist from topical vehicles with a hairless guinea pig model. Kumar, S., Malick, A.W., Meltzer, N.M., Mouskountakis, J.D., Behl, C.R. Journal of pharmaceutical sciences. (1992) [Pubmed]
  24. Aneuploidy induction in Saccharomyces cerevisiae by two solvent compounds, 1-methyl-2-pyrrolidinone and 2-pyrrolidinone. Mayer, V.W., Goin, C.J., Taylor-Mayer, R.E. Environ. Mol. Mutagen. (1988) [Pubmed]
  25. Size-exclusion chromatography of large molecules from coal liquids, petroleum residues, soots, biomass tars and humic substances. Herod, A.A., Zhuo, Y., Kandiyoti, R. J. Biochem. Biophys. Methods (2003) [Pubmed]
  26. Examination of soil contaminated by coal-liquids by size exclusion chromatography in 1-methyl-2-pyrrolidinone solution to evaluate interference from humic and fulvic acids and extracts from peat. Morgan, T.J., Herod, A.A., Brain, S.A., Chambers, F.M., Kandiyoti, R. Journal of chromatography. A. (2005) [Pubmed]
  27. Liquid chromatography-mass spectrometry and liquid chromatography-tandem mass spectrometry determination of N-methylpyrrolidinone in riverine biofilms. Headley, J.V., Peru, K.M., Friesen, D.A., Neu, T. Journal of chromatography. A. (2001) [Pubmed]
 
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