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Chemical Compound Review

PubChem10938     N-methylethanamide

Synonyms: HSDB 94, NSC-747, CHEMBL11544, NSC747, ACMC-1BL6E, ...
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Disease relevance of N-methylethanamide


High impact information on N-methylethanamide

  • Effective "dimerization" of dimethyl sulfoxide through a linear polymethylene chain increases its inducing activity by a magnitude similar to that observed when N-methylacetamide is effectively dimerized in such a manner [2].
  • In the present report, it is shown that this apparent hydrophobicity results from an underestimation of the free energy contribution that the methyl groups make to the transfer of N-methylacetamide from water to CCl4 [3].
  • Ab initio MP2 and density functional quantum chemistry calculations are used to explore geometries and vibrational properties of N-methylacetamide and of the alanine dipeptide with backbone angles characteristic of helix and sheet regions in proteins [4].
  • DFT calculations at the B3LYP/D95++(d,p) level of clusters of N-methylacetamide (NMA) with one, two, and three waters that were geometrically optimized on the counterpoise-corrected potential energy surfaces show that the gas-phase enthalpy of the interactions of NMA with three waters is -14.11 kcal/mol [5].
  • When some or all of the hydrogen atoms of formamide are replaced by methyl groups, the total number of water molecules hydrogen-bonding with the attacking hydroxide in the transition state decreases from three for formamide to two for N-methylacetamide, N,N-dimethylformamide (DMF), and N,N-dimethylacetamide (DMA) [6].

Biological context of N-methylethanamide


Associations of N-methylethanamide with other chemical compounds

  • Treatment of animals with N-methylacetamide, a diabetogen which does not cause insulin deficiency in the animal but rather produces an insulin-resistant state, did not affect the metabolism in vitro of either hexobarbital or aniline [12].
  • By carrying out molecular dynamics simulations of an N-methylacetamide (NMA) in methanol solution, the amide I mode frequency fluctuation and hydrogen bonding dynamics were theoretically investigated [13].
  • Apparently, the effects of poly-L-lysine were superior to those produced by N-methyl-acetamide, a potent inducer of differentiation "in vitro" [14].
  • Creatinine-adjusted NMAC concentration in urine for each volunteer within 12 h after the exposure was more closely correlated with the total excretion amount of NMAC up to 36 h than with urinary-volume-adjusted or specific-gravity-adjusted NMAC concentration in both the dermal and inhalation exposure experiments [15].

Analytical, diagnostic and therapeutic context of N-methylethanamide

  • The results of classical molecular dynamics (MD) simulations and Raman spectroscopy studies of neat liquid N-methylacetamide (NMA), the simplest model system relevant to the peptides, are reported as a function of temperature and pressure [16].


  1. Effects of N-methylacetamide and splenectomy on RF murine myeloid leukemia. Preisler, H., Bjornsson, S., Pavelic, Z. Leuk. Res. (1979) [Pubmed]
  2. Inducers of erythroleukemic differentiation. Relationship of structure to activity among planar-polar compounds. Reuben, R.C., Khanna, P.L., Gazitt, Y., Breslow, R., Rifkind, R.A., Marks, P.A. J. Biol. Chem. (1978) [Pubmed]
  3. Hydrophobicity of the peptide C=O...H-N hydrogen-bonded group. Roseman, M.A. J. Mol. Biol. (1988) [Pubmed]
  4. Calculations of NMR dipolar coupling strengths in model peptides. Case, D.A. J. Biomol. NMR (1999) [Pubmed]
  5. Enthalpies of Hydration of N-Methylacetamide by One, Two, and Three Waters and the Effect upon the C=O Stretching Frequency. An Ab Initio DFT Study. Dannenberg, J.J. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  6. Theoretical studies of the transition-state structures and free energy barriers for base-catalyzed hydrolysis of amides. Xiong, Y., Zhan, C.G. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory (2006) [Pubmed]
  7. Nucleic acid base-pairing and N-methylacetamide self-association in chloroform: affinity and conformation. Luo, R., Head, M.S., Given, J.A., Gilson, M.K. Biophys. Chem. (1999) [Pubmed]
  8. QM/MM study of the active site of free papain and of the NMA-papain complex. Han, W.G., Tajkhorshid, E., Suhai, S. J. Biomol. Struct. Dyn. (1999) [Pubmed]
  9. Toxicokinetics of dimethylacetamide (DMAc) in rat isolated perfused liver. Palmen, N.G., Evelo, C.T., Borm, P.J., Henderson, P.T. Human & experimental toxicology. (1993) [Pubmed]
  10. Dimethylacetamide pharmacokinetics following inhalation exposures to rats and mice. Hundley, S.G., Lieder, P.H., Valentine, R., McCooey, K.T., Kennedy, G.L. Toxicol. Lett. (1994) [Pubmed]
  11. Ultrafast vibrational spectroscopy of water and aqueous N-methylacetamide: Comparison of different electronic structure/molecular dynamics approaches. Schmidt, J.R., Corcelli, S.A., Skinner, J.L. The Journal of chemical physics. (2004) [Pubmed]
  12. Effect of experimental diabetes on drug metabolism in the rat. Ackerman, D.M., Leibman, K.C. Drug Metab. Dispos. (1977) [Pubmed]
  13. Non-Gaussian statistics of amide I mode frequency fluctuation of N-methylacetamide in methanol solution: linear and nonlinear vibrational spectra. Kwac, K., Lee, H., Cho, M. The Journal of chemical physics. (2004) [Pubmed]
  14. In vitro and in vivo studies of poly-L-lysine as inducer of Friend leukemic cells differentiation. Supino, R., Gibelli, N., Nano, R., Pezzoni, G., Zunino, F. Tumori. (1987) [Pubmed]
  15. Dermal absorption of N,N-dimethylacetamide in human volunteers. Nomiyama, T., Omae, K., Ishizuka, C., Yamauchi, T., Kawasumi, Y., Yamada, K., Endoh, H., Sakurai, H. International archives of occupational and environmental health. (2000) [Pubmed]
  16. Structure and hydrogen bonding in neat N-methylacetamide: classical molecular dynamics and Raman spectroscopy studies of a liquid of peptidic fragments. Whitfield, T.W., Martyna, G.J., Allison, S., Bates, S.P., Vass, H., Crain, J. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2006) [Pubmed]
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