1.0 2016-09-30 22:19:29 UTC 2020-06-04 20:48:45 UTC BMDB0000087 BMDB00087 Dimethylamine Dimethylamine, also known as DMA or HNME2, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Dimethylamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Dimethylamine exists in all living organisms, ranging from bacteria to humans. Dimethylamine is a potentially toxic compound. DMA HNMe2 Me2nh N,N-Dimethylamine (CH3)2nh Dimethylamine anhydrous Dimethylamine anhydrous (dot) Dimethylamine aqueous solution Dimethylamine hydrobromide Dimethylamine solution N-Methyl-methanamine N-Methylmethanamine N-Methylmethanamine (acd/name 4.0) Dimethylamine nitrate Dimethylamine perchlorate Dimethylamine sulfate Dimethylamine hydrochloride Dimethylamine phosphate (3:1) Dimethylamine, conjugate acid Dimethylammonium chloride Dimethylamine sulfate (1:1) Dimethylammonium formate Dimethylamine monosulfate C2H7N 45.0837 45.057849229 dimethylamine dimethylamine 124-40-3 CNC InChI=1S/C2H7N/c1-3-2/h3H,1-2H3 ROSDSFDQCJNGOL-UHFFFAOYSA-N belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Dialkylamines Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Secondary aliphatic amine Aliphatic acyclic compounds methylamines secondary aliphatic amine Liquid melting_point -92.2 °C water_solubility 1630 mg/mL at 40 °C logp -0.38 HANSCH,C ET AL. (1995) logp -0.53 ALOGPS logs 1.06 ALOGPS logp -0.19 ChemAxon pka_strongest_basic 10.52 ChemAxon iupac dimethylamine ChemAxon average_mass 45.0837 ChemAxon mono_mass 45.057849229 ChemAxon smiles CNC ChemAxon formula C2H7N ChemAxon inchi InChI=1S/C2H7N/c1-3-2/h3H,1-2H3 ChemAxon inchikey ROSDSFDQCJNGOL-UHFFFAOYSA-N ChemAxon polar_surface_area 12.03 ChemAxon refractivity 14.69 ChemAxon polarizability 5.75 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::NmrTwoD 1135 Specdb::CMs 20008 Specdb::CMs 29401 Specdb::CMs 99533 Specdb::CMs 137140 Specdb::CMs 144874 Specdb::EiMs 899 Specdb::MsIr 162 Specdb::MsIr 163 Specdb::MsIr 164 Specdb::NmrOneD 1077 Specdb::NmrOneD 1138 Specdb::NmrOneD 142090 Specdb::NmrOneD 142091 Specdb::NmrOneD 142092 Specdb::NmrOneD 142093 Specdb::NmrOneD 142094 Specdb::NmrOneD 142095 Specdb::NmrOneD 142096 Specdb::NmrOneD 142097 Specdb::NmrOneD 142098 Specdb::NmrOneD 142099 Specdb::NmrOneD 142100 Specdb::NmrOneD 142101 Specdb::NmrOneD 142102 Specdb::NmrOneD 142103 Specdb::NmrOneD 142104 Specdb::NmrOneD 142105 Specdb::NmrOneD 142106 Specdb::NmrOneD 142107 Specdb::NmrOneD 142108 Specdb::NmrOneD 142109 Specdb::NmrOneD 166489 Specdb::MsMs 6123 Specdb::MsMs 6124 Specdb::MsMs 6125 Specdb::MsMs 6126 Specdb::MsMs 6127 Specdb::MsMs 6128 Specdb::MsMs 310543 Specdb::MsMs 310544 Specdb::MsMs 310545 Specdb::MsMs 355297 Specdb::MsMs 355298 Specdb::MsMs 355299 Specdb::MsMs 446053 Specdb::MsMs 446054 Specdb::MsMs 446055 Specdb::MsMs 446056 Specdb::MsMs 446057 Specdb::MsMs 2326977 Specdb::MsMs 2326978 Specdb::MsMs 2326979 Specdb::MsMs 2612029 Specdb::MsMs 2612030 Specdb::MsMs 2612031 Blood Samples collected from 54 Holstein cows Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21. 23394630 Blood Detected by NMR De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014. 25372282 Blood Detected by NMR in male Charolais cows. Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28. 22370585 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk 15 +/- 1 uM 1% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 17 +/- 1 uM 2% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 17 +/- 1 uM 3.25% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 17 +/- 2 uM Skim milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 9.95 +/- 1.96 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Milk 9.40 +/- 2.30 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Milk Samples collected from 54 Holstein cows Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21. 23394630 Milk 14.60 +/- 2.77 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Neuron Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Ruminal Fluid 7.59 uM By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter) Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid 29.5 uM By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter) Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid 33.7 uM By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter) Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid 4.36 uM By NMR. Primiparous Holstein cows, no barley grains in diet. Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid Detected by NMR in bovines in growth and fattening stages. Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 Ruminal Fluid Detected by NMR in bovines in growth and fattening stages. Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 Ruminal Fluid Detected by NMR in bovines in growth and fattening stages. Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub 2012 Jun 15. 22706048 Ruminal Fluid 21.4 uM By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 47.1 uM By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 51.6 uM By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 9.5 uM By NMR. No barley grains in diet (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 22 +/- 6 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 47 +/- 45 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 52 +/- 31 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 10 +/- 2 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. C00543 FDB012589 654 674 17170 DIMETHYLAMINE Dimethylamine 3758 Zones, Stacey I.; Burton, Allen W. Production of methylamine and dimethylamine using STI zeolite catalysts. U.S. Pat. Appl. Publ. (2007), 6pp. Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21. 23394630 O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP00611 N(G),N(G)-dimethylarginine dimethylaminohydrolase 2 Q3SX44 DDAH2 Enzyme BMDBP00612 N(G),N(G)-dimethylarginine dimethylaminohydrolase 1 P56965 DDAH1 Enzyme