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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 127-19-5, Dimethylacetamide, Acetamide, n,n-dimethyl-, Dmac, Acetdimethylamide, Dimethyl acetamide

Molecular Formula

C₄H₉NO

Molecular Weight

87.12 g/mol

InChI Key

FXHOOIRPVKKKFG-UHFFFAOYSA-N

FDA UNII

JCV5VDB3HY

N,N-Dimethylacetamide is a dipolar aprotic solvent and reagent that may be used in the production of fibers and pharmaceuticals, and as a non-aldehyde fixative.

1 2D Structure

N,N-Dimethylacetamide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N,N-dimethylacetamide

2.1.2 InChI

InChI=1S/C4H9NO/c1-4(6)5(2)3/h1-3H3

2.1.3 InChI Key

FXHOOIRPVKKKFG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(=O)N(C)C

2.2 Other Identifiers

2.2.1 UNII

JCV5VDB3HY

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Dimethylacetamide

2.3.2 Depositor-Supplied Synonyms

1. 127-19-5

2. Dimethylacetamide

3. Acetamide, N,n-dimethyl-

4. Dmac

5. Acetdimethylamide

6. Dimethyl Acetamide

7. N,n-dimethyl Acetamide

8. Dimethylamide Acetate

9. N,n-dimethylethanamide

10. Acetic Acid, Dimethylamide

11. Dimethylacetone Amide

12. Nsc 3138

13. N.n-dimethylacetamide

14. Hallucinogen

15. Cbc 510337

16. Sk 7176

17. Dimethylamid Kyseliny Octove

18. Mfcd00008686

19. Acetyl Dimethylamine

20. U-5954

21. N, N-dimethylacetamide

22. N,n-dimethyl-acetamide

23. Jcv5vdb3hy

24. Dtxsid5020499

25. Chebi:84254

26. Nsc-3138

27. Dsstox_cid_499

28. Acetyldimethylamine

29. Dsstox_rid_75625

30. Dsstox_gsid_20499

31. Cas-127-19-5

32. Hsdb 74

33. Ccris 4623

34. N,n-dimethylacetoamide

35. Unii-jcv5vdb3hy

36. Acetic Acid Dimethylamide

37. Dimethylamid Kyseliny Octove [czech]

38. Einecs 204-826-4

39. Dimethyacetamide

40. Dimethylactamide

41. N,n-dimethylacetamide Solution

42. Dimethylacteamide

43. Ai3-15276

44. Trimethylformamide

45. Dimeihyl Acetamide

46. Dimethyl-acetamide

47. N-dimethylacetamide

48. N,n-dimethyacetamide

49. N,n-dimethylactamide

50. N-acetyldimethylamine

51. N,n Dimethylacetamide

52. N,n,-dimethylacetamide

53. N,-n-dimethylacetamide

54. N,n -dimethylacetamide

55. N,n-di-methylacetamide

56. N,n-dimethylacet-amide

57. N, N-dimethylacetoamide

58. N,n-dimethyl Acetoamide

59. Dmac, Dimethylacetamide

60. N,n,-dimethyl-acetamide

61. Acetic Acid-dimethylamide

62. N,n-dimethyl- Acetamide

63. Ec 204-826-4

64. N,n-dimethylacetamide Solution (40% Or Less)

65. N,n-dimethyl-n-acetylamine

66. Ch3con(ch3)2

67. N, N-dimethylacetamide, Ep

68. Chembl11873

69. N,n-dimethylacetamide, >=99%

70. N,n-dimethylacetamide, Anhydrous

71. Dimethylacetamide [mart.]

72. Nsc3138

73. N,n-dimethylacetamide [ii]

74. N,n-dimethylacetamide [mi]

75. Wln: 1vn1 & 1

76. N,n-dimethylacetamide, Hplc Grade

77. Zinc1666602

78. Tox21_202174

79. Tox21_302787

80. N,n-dimethylacetamide [hsdb]

81. Nsc820333

82. Stl482892

83. N,n-dimethylacetamide [vandf]

84. Acetic Acid,amide,n,n-dimethyl

85. Akos000118789

86. N,n-dimethylacetamide-1,2-[13c2]

87. Cs-w023195

88. Hy-w042416

89. N,n-dimethylacetamide [usp-rs]

90. Nsc-820333

91. Dimethylacetamide [ep Monograph]

92. N,n-dimethylacetamide, P.a., 99.5%

93. N,n-dimethylacetamide, Ar, >=99.5%

94. Ncgc00159401-02

95. Ncgc00159401-03

96. Ncgc00256375-01

97. Ncgc00259723-01

98. Bp-31151

99. N,n-dimethylacetamide, Saj Special Grade

100. N,n-dimethylacetamide, Analytical Standard

101. N,n-dimethylacetamide, Anhydrous, 99.8%

102. Db-041302

103. D0641

104. Ft-0629514

105. Ft-0642826

106. N,n-dimethylacetamide, For Hplc, >=99.7%

107. N,n-dimethylacetamide, For Hplc, >=99.9%

108. N,n-dimethylacetamide, Reagentplus(r), 99%

109. C20339

110. N,n-dimethylacetamide, Reagentplus(r), >=99%

111. Q411452

112. Residual Solvent Class 2 - N,n-dimethylacetamide

113. N,n-dimethylacetamide, Saj First Grade, >=99.0%

114. N,n-dimethylacetamide, Uv Hplc Spectroscopic, 99%

115. W-108388

116. N,n-dimethylacetamide, Anhydrous, Zero2(tm), 99.8%

117. N,n-dimethylacetamide, Vetec(tm) Reagent Grade, 98%

118. Z32014266

119. Acetic Acid-dimethylamide 100 Microg/ml In Acetonitrile

120. F0001-0392

121. N,n-dimethylacetamide, Puriss. P.a., >=99.5% (gc)

122. N,n-dimethylacetamide, Spectrophotometric Grade, >=99%

123. Acetic Acid-dimethylamide 1000 Microg/ml In Acetonitrile

124. N,n-dimethylacetamide, For Peptide Synthesis, >=99.8% (gc)

125. 5y9

126. N,n-dimethylacetamide, Pharmagrade, Manufactured Under Appropriate Gmp Controls For Pharma And Biopharmaceutical Production., Ph Eur

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₄H₉NO
Molecular Weight	87.12 g/mol
XLogP3	-0.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	0
Exact Mass	87.068413911 g/mol
Monoisotopic Mass	87.068413911 g/mol
Topological Polar Surface Area	20.3 Å²
Heavy Atom Count	6
Formal Charge	0
Complexity	58.6
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Commercial solvent tested as a parenteral drug vehicle and as an antitumor agent.

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-200

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Cryoprotective Agents

Substances that provide protection against the harmful effects of freezing temperatures. (See all compounds classified as Cryoprotective Agents.)

5.2 Absorption, Distribution and Excretion

/N,N-DIMETHYLACETAMIDE/ ... READILY ABSORBED THROUGH SKIN ... .

Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1834

N,N-dimethylacetamide is rapidly absorbed through biological membranes.

PMID:3530639 Kennedy GL Jr; Crit Rev Toxicol 17 (2): 129-82 (1986)

No correlation between personal airborne exposure and excretion of mono-methylacetamide in urine was detected during a full workshift (5 days). Most (n = 6) workers studied (n = 8) excreted about 13% of the calculated inhaled dose as metabolite in urine.

PMID:3681500 Borm PJ et al; J Occup Med 29 (11): 898-903 (1987)

DMAC is readily absorbed in man after oral, dermal, or inhalation exposure. ... About 2% of a dose of dimethylacetamide is recovered in the urine as MMAC /N-methylacetamide/ after inhalation; 10% is recovered after inhalation plus skin exposure. Exposure to 10 ppm of DMAC results in complete excretion of MMAC with in 30 hr. Maximal concns of 45 & 100 ppm (mg/L) of MMAC in the urine are found in subjects exposed both by inhalation & skin. In workers continuously exposed to DMAC vapor (inhalation plus skin) & subjected to DMAC airborne levels of 6-22 ppm ..., about 13.5% of the estimated dose is excreted as MMAC in the urine. Some workers may excrete about 30% of a dose as MMAC.

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. 1673

For more Absorption, Distribution and Excretion (Complete) data for N,N-DIMETHYLACETAMIDE (7 total), please visit the HSDB record page.

5.3 Metabolism/Metabolites

N-DEMETHYLATION OF ... DIMETHYLACETAMIDE OCCURRED IN RAT, RESPECTIVE MONOMETHYLAMIDES APPEARING IN URINE ... IN THE CASE OF DIMETHYLACETAMIDE WAS DIDEMETHYLATED PRODUCT, ACETAMIDE, ALSO FOUND.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 429

ANALYSIS OF HUMAN URINE AFTER OCCUPATIONAL EXPOSURE TO DIMETHYLACETAMIDE SHOWS N-METHYLACETAMINE. /FROM TABLE/

Doull, J., C.D. Klaassen, and M. D. Amdur (eds.). Casarett and Doull's Toxicology. 2nd ed. New York: Macmillan Publishing Co., 1980., p. 707

Gas chromatographic analysis of the urine of rats which had received dimethylacetamide by the subcutaneous route indicated the presence of N-methyl-acetamide and acetamide. Both metabolites were also found ... in incubation mixtures of dimethylacetamide with rat liver homogenate. N-Methylacetamide was detected in the urine of human volunteers who had inhaled dimethylacetamide or absorbed dimethylacetamide vapor through the skin. Measurement of the amount of the metabolite N-methylacetamide excreted by individuals exposed to dimethylacetamide vapors with or without face masks which allowed the inhalation of air free of dimethylacetamide indicated that more dimethylacetamide was absorbed through the lung than through the skin. ... Only 2-10% of the amount of dimethylacetamide inhaled was recovered in the urine in the form of N-methylacetamide. It has been suggested that the major urinary metabolite of the analogous dimethylformamide is N-(hydroxymethyl)-N-methylformamide and not N-methylformamide, since the carbinolamide decomposes on the gas chromatography column (to N-methylformamide) but is relatively stable in aqueous solution. In analogy, it would be logical to assume that the N-methylacetamide found in the urine after exposure to dimethylacetamide really arose from chemical breakdown of N-(hydroxymethyl)-N-methylacetamide during the analytical process.

Snyder, R. (ed.). Ethel Browning's Toxicity and Metabolism of Industrial Solvents. 2nd ed. Volume II: Nitrogen and Phosphorus Solvents. Amsterdam-New York-Oxford: Elsevier, 1990., p. 144

N,N-dimethylacetamide is metabolized by demethylation first to monomethyl derivatives and then to the parent acetamide.

PMID:3530639 Kennedy GL Jr; Crit Rev Toxicol 17 (2): 129-82 (1986)

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