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2D Structure
Also known as: N-methylmethanamine, 124-40-3, N,n-dimethylamine, Methanamine, n-methyl-, Dimethyl-amine, Dimethylamine anhydrous
Molecular Formula
C2H7N
Molecular Weight
45.08  g/mol
InChI Key
ROSDSFDQCJNGOL-UHFFFAOYSA-N
FDA UNII
ARQ8157E0Q

Dimethylamine is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Dimethylamine (DMA) is an organic secondary amine. It is a colorless, liquefied and flammable gas with an ammonia and fish-like odor. Dimethylamine is abundantly present in human urine. Main sources of urinary DMA have been reported to include trimethylamine N-oxide, a common food component, and asymmetric dimethylarginine (ADMA), an endogenous inhibitor of nitric oxide (NO) synthesis. ADMA is excreted in the urine in part unmetabolized and in part after hydrolysis to DMA by dimethylarginine dimethylaminohydrolase (DDAH). Statistically significant increases in urinary DMA have been found in individuals after the consumption of fish and seafoods. The highest values were obtained for individuals that consumed coley, squid and whiting with cod, haddock, sardine, skate and swordfish As a pure chemical substance Dimethylamine is used as dehairing agent in tanning, in dyes, in rubber accelerators, in soaps and cleaning compounds and as an agricultural fungicide. In the body, DMA also undergoes nitrosation under weak acid conditions to give dimethlynitrosamine.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-methylmethanamine
2.1.2 InChI
InChI=1S/C2H7N/c1-3-2/h3H,1-2H3
2.1.3 InChI Key
ROSDSFDQCJNGOL-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CNC
2.2 Other Identifiers
2.2.1 UNII
ARQ8157E0Q
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Dimethylamine Hydrochloride

2. Dimethylamine Monosulfate

3. Dimethylamine Nitrate

4. Dimethylamine Perchlorate

5. Dimethylamine Phosphate (3:1)

6. Dimethylamine Sulfate

7. Dimethylamine Sulfate (1:1)

8. Dimethylamine, Conjugate Acid

9. Dimethylammonium Chloride

10. Dimethylammonium Formate

2.3.2 Depositor-Supplied Synonyms

1. N-methylmethanamine

2. 124-40-3

3. N,n-dimethylamine

4. Methanamine, N-methyl-

5. Dimethyl-amine

6. Dimethylamine Anhydrous

7. Dimethylamine (anhydrous)

8. Rcra Waste Number U092

9. Dimethylamine Solution

10. (ch3)2nh

11. Dimethylamine Aq

12. Nsc 8650

13. Hnme2

14. Me2nh

15. Dimethylamine Aqueous Solution

16. Arq8157e0q

17. Chebi:17170

18. Nsc-8650

19. Dimethylamin

20. Dimethyl Amine

21. Dimethylamine, Purum, >=99.0%

22. Mfcd00008288

23. Ccris 981

24. Dimethylamine Solution, 40 Wt. % In H2o

25. Hsdb 933

26. Dimethylamine, In Aqueous Solution

27. Einecs 204-697-4

28. Ai3-15638-x

29. Un1032

30. Un1160

31. Rcra Waste No. U092

32. Dimethlamine

33. Dimethlyamine

34. Dimethyamine

35. Dimethylammonia

36. Dimethylarnine

37. Dimetylamine

38. Dirnethylamine

39. Unii-arq8157e0q

40. Di-methylamine

41. Dimetyl Amine

42. N,n-dimethylamin

43. N,n Dimethylamine

44. N,n Dimethyl Amine

45. N,n- Dimethylamine

46. N,n-dimethyl Amine

47. Dimethylamine Solution (over 55% But Not Over 65%)

48. N-methyl-methanamine

49. Dimethylamine Solution (45% Or Less)

50. N, N-dimethyl Amine

51. Nhme2

52. N-methyl-1-methanamine

53. Dimethylamine, Anhydrous

54. Dsstox_cid_4057

55. Dimethylamine [mi]

56. Dimethylamine Reagent Grade

57. Nh(me)2

58. Ec 204-697-4

59. Methylaminomethylidyneradical

60. Dimethylamine [hsdb]

61. Dimethylamine, >=99.8%

62. Dsstox_rid_77272

63. Nciopen2_007708

64. Dsstox_gsid_24057

65. Dimethylamine Anhydrous (dot)

66. Un 1160 (salt/mix)

67. Chembl120433

68. Dimethylamine Solution (over 45% But Not Over 55%)

69. Gtpl5177

70. Nh(ch3)2

71. Wln: 1m1

72. Dtxsid5024057

73. Nsc8650

74. Dimethylamine, Anhydrous, >=99%

75. Dimethylamine (~2.0 M In Thf)

76. Str00287

77. Tox21_302439

78. Bdbm50416497

79. Dimethylamine Solution 40% In Water

80. Dimethylamine, 2m In Tetrahydrofuran

81. Nsc187661

82. Stl263869

83. N-methylmethanamine (acd/name 4.0)

84. Akos008968166

85. Dimethylamine Solution 1.0 M In Thf

86. Dimethylamine Solution 2.0 M In Thf

87. Nsc-187661

88. Un 1032

89. Dimethylamine Solution, 2.0 M In Thf

90. Dimethylamine (ca. 8% In Acetonitrile)

91. Dimethylamine Solution 2.0m In Methanol

92. Dimethylamine, 40% W/w Aqueous Solution

93. Ncgc00255288-01

94. Cas-124-40-3

95. Dimethylamine Solution, 2.0 M In Methanol

96. Dimethylamine Solution, Cp, 50% In H2o

97. D0643

98. D3292

99. D3936

100. D3948

101. D4198

102. D5884

103. D5885

104. Dacarbazine Impurity D [ep Impurity]

105. C00543

106. Dimethylamine (ca. 7% In N,n-dimethylformamide)

107. Q408022

108. Molybdoceric Acid (h8 Ce Mo12 O42), Eicosahydrate

109. Dimethylamine Solution [un1160] [flammable Liquid]

110. Dimethylamine, 40% W/w Aqueous Solution, In Ampoule

111. Dimethylamine, Anhydrous [un1032] [flammable Gas]

112. Z57834054

113. Metformin Hydrochloride Impurity F [ep Impurity]

114. Dimethylamine Solution, Purum, 33% In Absolute Ethanol (~5.6 M)

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 45.08 g/mol
Molecular Formula C2H7N
XLogP3-0.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area12
Heavy Atom Count3
Formal Charge0
Complexity2.8
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

The disposition and pharmacokinetics of [(14)C]dimethylamine [(14)C] DMA) following 6-hr inhalation of either 10 or 175 ppm were determined in male Fischer 344 rats. Seventy-two hours after termination of exposure, the disposition of recovered radioactivity was similar for each airborne concentration, with more than 90% in the urine and feces, 7 to 8% in selected tissues and the carcass, and 1.5% exhaled as (14)CO2. Over 98% of the radioactivity in the urine was unmetabolized DMA. Analysis of tissue radioactivity immediately after exposure to [(14)C]DMA showed that the respiratory nasal mucosa contained the highest concentration of (14)C, followed by the olfactory nasal mucosa; concentrations of (14)C in liver, lung, kidney, brain, and testes were approximately 2 orders of magnitude less than in the nasal mucosal tissues. Radioactivity in plasma of rats exposed by inhalation to 175 ppm of [(14)C]DMA decayed in a biphasic manner. The terminal half-life for plasma radioactivity was similar to the half-lives of some plasma proteins, suggesting incorporation of (14)C into proteins subsequent to metabolism of [(14)C]DMA. The results indicate that, while most of the inhaled DMA is excreted unchanged, a small amount of oxidative metabolism of DMA occurs.

PMID:6138225 McNulty MJ, Heck HD; Drug Metab Dispos 11 (5): 417-20 (1983)


1. The fate of [(14)C]-dimethylamine was investigated following oral administration to four male volunteers. 2. The major route of excretion was urine, with 94% of the administered radioactivity being voided over 3 days (87% during the first 24 hr). Small amounts (1-3%) of radioactivity were found in the faeces and expired air. 3. Metabolism was limited with only 5% being demethylated to methylamine. The remainder of the dose was excreted unchanged. 4. Pharmacokinetic studies indicated rapid (t1/2ab = 8 min) and extensive absorption (bioavailability = 82%) from the gastrointestinal tract followed by widespread distribution and a fairly prompt excretion (t1/2el = 6-7 hr) with a plasma clearance of 190 mL/min.

PMID:8059541 Zhang AQ et al; Xenobiotica 24 (4): 379-87 (1994)


The urinary excretion of dimethylamine has been measured in 203 unrelated healthy volunteers (102 male) who maintained their normal diets. ... The average daily output was 17.43 +/- 11.80 mg (mean +/- SD) (21.21 +/- 14.78 male; 13.74 +/- 5.65 female) with values for the majority of the population lying within the 0.68-35.72 mg range. Four male outliers excreted up to 109.2 mg; these large amounts of dimethylamine were presumed to be of dietary origin. ...

PMID:7758205 Zhang AQ et al; Clin Chim Acta 233 (1-2): 81-8 (1995)


In the gastro-intestinal tract of male Wistar rats fed a commercial diet containing 23.6 ppm dimethylamine (DMA), the concentration of DMA was highest (11.2 +/- 2.1 ppm) in the stomach and declined towards the lower regions. In contrast, the highest DMA concentration (6.6 +/- 2.5 ppm) was observed in the upper small intestine in rats fed a diet containing only 1.0 ppm DMA. DMA was absorbed in the intestines, and the disappearance curves were monoexponential. The t1/2 values for DMA in the ligated stomach, upper and lower small intestine, caecum and large intestine were 198, 8.3, 11.6, 31.5 and 11.0 min, respectively. The DMA concentration in the blood had increased to 3.0 +/- 1.0 ppm (from a pre-injection level of 0.28 +/- 0.06 ppm) 5 min after the injection of 250 micrograms DMA into the ligated upper small intestine. The disappearance curve for DMA in the blood was monoexponential and the t1/2 for the initial 15 min was 12.5 min when 250 micrograms DMA was injected into a femoral vein. The peak concentrations of DMA in the intestine and bile, respectively, were 15.6 +/- 12.6 ppm (at 15 min) and 3.7 +/- 1.9 ppm (at 30 min after the iv injection of DMA). In this 30-min period, urinary DMA increased from 17.3 +/- 9.4 to 139 +/- 23 ppm. These results show that, following ingestion, DMA is absorbed from the intestine into the blood, from which it disappears rapidly, the major part being excreted in the urine while a small proportion is excreted in the bile or secreted into the intestine, where it may be reabsorbed.

PMID:6540740 Ishiwata H et al; Food Chem Toxicol 22 (8): 649-53 (1984)


For more Absorption, Distribution and Excretion (Complete) data for Dimethylamine (12 total), please visit the HSDB record page.


4.2 Metabolism/Metabolites

It is extensively absorbed (bioavailability 72%); 5% is demethylated to methylene, but 95% is secreted unchanged in the urine.

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 1427


The intragastric formation of nitrosodimethylamine (NDA) by bacteria existing in the gastrointestinal tract of monkey was examined by determining the in vitro formation of nitrosodimethylamine from nitrite and dimethylamine in the brain-heart-infusion (BHI) medium, adjusted to pH 6 with gastric juice containing 5000 ppm sodium nitrate and 1000 ppm dimethylamine. Nitrosodimethylamine formation depended on the activity of the nitrate-reducing bacteria in the stomach contents of the monkey, and the concn of nitrite was clearly related to the amount of nitrosodimethylamine. NDA was formed in the brain-heart-infusion medium alone at pH 5 and 6. The addition of gastric juice to the medium increased the formation of nitrosodimethylamine.

Hayashi N et al; Eisei Shikensho Hokoku 100: 72-6 (1982)


The extent of nitrosamine formation and the metabolism of the resultant nitrosamines in vivo were investigated by using (15)N-stable isotope labeling and by the determination of the isotope ratio in the expired N. (15)N-labeled dimethylamine (1.1 mmol/kg) and various doses of nonlabeled nitrile (0.55-2.2 mmol/kg) or labeled nitrile without dimethylamine administered to male rats, which were placed in an enclosed respiratory system. The system was flushed with a mixture containing 80% He and 20% O, and N content of the recirculating atmosphere was determined. When labeled dimethylamine and nonlabeled nitrile were administered, nitrile reacted with secondary amines, followed by enzymic alpha-hydroxylation and decomposition of the ensuing alkyldiazohydroxide to molecular N and an alkyl cation as ultimate carcinogen. When (15)N nitrile was administered, N was released (nitrile reacted with primary amines to release molecular N and formation of the corresponding alcohol or olefin).

Frank H et al; Fresenius Z Anal Chem 317 (6): 660 (1984)


Dimethylamine is the immediate precursor of dimethylnitrosamine, a known potent carcinogen in a wide variety of animal species. Although small amounts of dimethylamine are ingested directly, the major dietary source is believed to be via choline and related materials. Owing to quantitative recoveries following oral administration, urinary dimethylamine levels provide good overall measures of body exposure. The oral administration of equimolar amounts (1 mmol/kg body weight) of potential amine precursors to male Wistar rats produced only small increases in urinary dimethylamine after choline (+ 11%; 0.60 +/- 0.36% dose), dimethylaminopropanol (+ 32%; 1.49 +/- 0.30% dose), dimethylaminoethyl chloride (+ 110% 5.38 +/- 1.72% dose) and trimethylamine (+ 51%; 1.6 +/- 0.80% dose) input, whereas significantly larger increases were found following trimethylamine N-oxide ingestion (+ 355%; 12.93 +/- 1.13% dose; t-test, P < 0.001). These data suggest that trimethylamine N-oxide is a major dietary source of dimethylamine, by direct conversion and not by sequential reduction (to trimethylamine) and demethylation, and that in this respect it is of greater importance, on a molar basis, than choline.

PMID:9771553 Zhang AQ et al; Food Chem Toxicol 36 (11): 923-7 (1998)


Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.