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Lauramine Oxide
Also known as: 1643-20-5, Lauryldimethylamine oxide, Dodecyldimethylamine oxide, Lauryldimethylamine n-oxide, 1-dodecanamine, n,n-dimethyl-, n-oxide, Ldao
Molecular Formula
C14H31NO
Molecular Weight
229.40  g/mol
InChI Key
SYELZBGXAIXKHU-UHFFFAOYSA-N
FDA UNII
4F6FC4MI8W

lauryl dimethylamine-N-oxide is a natural product found in Euglena gracilis with data available.
1 2D Structure

Lauramine Oxide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N,N-dimethyldodecan-1-amine oxide
2.1.2 InChI
InChI=1S/C14H31NO/c1-4-5-6-7-8-9-10-11-12-13-14-15(2,3)16/h4-14H2,1-3H3
2.1.3 InChI Key
SYELZBGXAIXKHU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCCCCCCCC[N+](C)(C)[O-]
2.2 Other Identifiers
2.2.1 UNII
4F6FC4MI8W
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ammonyx Lo

2. Ddao

3. Dodecyldimethylamine N-oxide

4. Dodecyldimethylamine Oxide

5. Hexyldimethylamine Oxide

6. Lauryldimethylamine Oxide

7. Ldao

8. N,n-dimethyldodecyclamine N-oxide

9. N,n-dimethyldodecylamine-n-oxide

10. N-dodecyl-n,n-dimethylamine N-oxide

2.3.2 Depositor-Supplied Synonyms

1. 1643-20-5

2. Lauryldimethylamine Oxide

3. Dodecyldimethylamine Oxide

4. Lauryldimethylamine N-oxide

5. 1-dodecanamine, N,n-dimethyl-, N-oxide

6. Ldao

7. N,n-dimethyldodecan-1-amine Oxide

8. Ammonyx Ao

9. Empigen Ob

10. Ammonyx Lo

11. Aromox Dmcd

12. Conco Xal

13. Dimethylaurylamine Oxide

14. N,n-dimethyldodecylamine N-oxide

15. Dimethyldodecylamine Oxide

16. N-dodecyldimethylamine Oxide

17. Dimethyldodecylamine N-oxide

18. Dodecyldimethylamine N-oxide

19. Dodecyl(dimethyl)amine Oxide

20. Ddno

21. N,n-dimethyldodecylamine-n-oxide

22. Lauryl Dimethylamine-n-oxide

23. Dimethyllaurylamine Oxide

24. N,n-dimethyldodecylamine Oxide

25. N,n-dimethyl-1-dodecylamine N-oxide

26. Laurylamine Oxide

27. Lauryl Dimethyl Amine Oxide

28. N,n-dimethyl-1-dodecanamine-n-oxide

29. 4f6fc4mi8w

30. Amine Oxide, Dodecyl(dimethyl)-

31. Chembl1233973

32. Aromox Dmmc-w

33. Amonyx Ao

34. Refan [russian]

35. N,n-dimethyldodecylamine N-oxide 30% Solution In H2o

36. Refan

37. N-lauryldimethylamine N-oxide

38. Hsdb 5451

39. N-lauryl-n,n-dimethylamine Oxide

40. Nci-c55129

41. Einecs 216-700-6

42. N,n-dimethyl-dodecylaminoxid [czech]

43. Oxyde De Dimethyllaurylamine [french]

44. Unii-4f6fc4mi8w

45. Dodecylamine, N,n-dimethyl-, N-oxide

46. Oxyde De Dimethyllaurylamine

47. Brn 1769927

48. N,n-dimethyl-dodecylaminoxid

49. 1-dodecanamine, N,n-dimethl-, N-oxide

50. N,n-dimethyldodecanamine Oxide

51. Cyclomox L

52. Rhodamox L

53. Softamine L

54. Genaminox La

55. Schercamox Dml

56. Rhodamox Lo

57. Oxamin Lo

58. Emcol L

59. Incromine Oxide L

60. Emcol Lo

61. Unisafe A-lm

62. Amphitol 20n

63. Barlox 12i

64. Mfcd00002049

65. N,n-dimethyldodecan-1-amine N-oxide

66. Rewominox L 408

67. Ammonyx Dmcd 40

68. Admox 12

69. Aromox Dm 12d

70. Aromox Dm 12w

71. Oxidet Dm 20

72. Euroxide Lo

73. Aromox Dm 12d-w

74. Emal 20n

75. Imethylauroylamine Oxide

76. Atlas Cd 413

77. Tomah Ao 728

78. Aromox Dm 12dw(c)

79. Ammonyx C10 Amine Oxide

80. Lauryldimethylamine-n-oxide

81. Ec 216-700-6

82. N,n-dimethyl Lauramine Oxide

83. Schembl27337

84. Lauramine Oxide [ii]

85. 4-04-00-00798 (beilstein Handbook Reference)

86. Lauramine Oxide [hsdb]

87. Lauramine Oxide [inci]

88. Dtxsid1020514

89. Chebi:131762

90. (c10-16)alkyldimethylamine Oxide

91. 101cg

92. Zinc2039372

93. Bdbm50327308

94. Akos015904034

95. Db04147

96. Ncgc00164286-01

97. N,n-dimethyldodecylamine N-oxide Solution

98. Lauryldimethylamine Oxide / Lauramine Oxide

99. Ft-0689256

100. L0361

101. D78505

102. 1-dodecanamine, N,n-dimethyl-, N-oxide (9ci)

103. Ldao, N,n-dimethyldodecylamine N-oxide, Powder

104. Dodecylamine, N,n-dimethyl-, N-oxide (6ci,8ci)

105. N,n-dimethyldodecylamine N-oxide 100 Mm Solution

106. J-010130

107. J-521637

108. Q6501952

109. N,n-dimethyldodecylamine N-oxide (ca. 30% In Water)

110. N,n-dimethyldodecylamine N-oxide, >=99% (titration)

111. N,n-dimethyldodecylamine N-oxide Solution, ~30% In H2o

112. N,n-dimethyldodecylamine N-oxide, Bioxtra, >=99.0% (nt)

113. N,n-dimethyldodecylamine N-oxide Solution, Bioultra, ~0.1 M In H2o

2.4 Create Date
2005-06-01
3 Chemical and Physical Properties
Molecular Weight 229.40 g/mol
Molecular Formula C14H31NO
XLogP35.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count11
Exact Mass229.240564612 g/mol
Monoisotopic Mass229.240564612 g/mol
Topological Polar Surface Area18.1 Ų
Heavy Atom Count16
Formal Charge0
Complexity146
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 MeSH Pharmacological Classification

Surface-Active Agents

Agents that modify interfacial tension of water; usually substances that have one lipophilic and one hydrophilic group in the molecule; includes soaps, detergents, emulsifiers, dispersing and wetting agents, and several groups of antiseptics. (See all compounds classified as Surface-Active Agents.)


Detergents

Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties. (See all compounds classified as Detergents.)


4.2 Absorption, Distribution and Excretion

(1-Dodecyl-14C)lauramine oxide (10 mg with 100 uCi of 14C) was applied to the skin of two humans to study cutaneous absorption and metabolism of lauramine oxide. Ninety-two percent of the applied radioactivity was recovered from the skin of the test subjects 8 hr after dosing, and 0.1 and 0.23% of the radioactivity was recovered from the excretion products of the test subjects. The stratum corneum contained <0.2% of the applied dose.

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Lauramine Oxide and Stearamine Oxide; Journal of American College of Toxicology 13 (3): 231-45 (1994)


Oral administration of a solution containing 50 mg (1-dodecyl-14C)lauramine oxide (100 uCi of 14C) to two humans resulted in excretion patterns of radioactivity similar to that of the other species studied. Fifty percent and 37% of the radioactivity was found in the urine within 24 hr of dosing, and expired 14C02 contained between 18 and 22% of the radioactivity administered.

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Lauramine Oxide and Stearamine Oxide; Journal of American College of Toxicology 13 (3): 231-45 (1994)


Four Sprague-Dawley rats were given intraperitoneal injections of 22 mg (methyl-14C)lauramine oxide kg (specific activity 1.3 mCi/g). Sixty-seven percent of the total radioactivity was eliminated in the urine, 8% was expired as I4CO2, and 6% was eliminated in the feces within 24 hr. The distribution of radioactivity was essentially the same as that seen in rats given oral doses of lauramine oxide. The conclusion was that "... microbial metabolism by gastrointestinal flora does not play a major role in the absorption and excretion of [lauramine oxide] in rats."

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Lauramine Oxide and Stearamine Oxide; Journal of American College of Toxicology 13 (3): 231-45 (1994)


Aqueous (methyl-14C)lauramine oxide (10 mg containing 1.3 mCi/g) was applied to the skin of four Sprague-Dawley rats to test metabolism and absorption of the compound. Over 72 hr, 14.2% of the total radioactivity was found in the urine, 2.5% in the CO2, and 1.8% in the feces. Radioactivity was detected in the liver, kidneys, testes, blood, and expired CO2.

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Lauramine Oxide and Stearamine Oxide; Journal of American College of Toxicology 13 (3): 231-45 (1994)


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


4.3 Metabolism/Metabolites

Metabolic profiles for different species (rat, human, mouse, rabbit) did not have any significant differences in metabolites, but the degree of absorption, especially in cutaneous applications, varied from species to species.

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Lauramine Oxide and Stearamine Oxide; Journal of American College of Toxicology 13 (3): 231-45 (1994)


Characterization of metabolites of lauramine oxide resulted in the positive identification of only one metabolite, N-dimethyl-4-aminobutyric acid N-oxide. Several pathways exist for metabolism of lauramine oxide: omega,beta-oxidation of alkyl chains (the most common pathway for surfactant metabolism), hydroxylation of alkyl chains, and reduction of the amine oxide group.

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Lauramine Oxide and Stearamine Oxide; Journal of American College of Toxicology 13 (3): 231-45 (1994)


Urinary metabolites in rats, rabbits and humans suggested metabolism via omega, beta-oxidation of the aliphatic chain, amine oxide reduction and aliphatic, mid-chain hydroxylation. N,N-dimethyl-4-aminobutyric acid and its N-oxide accounted for 28, 28 and 23% in man, rats and rabbits, respectively.

PMID:7293233 Turan et al; Xenobiotica 11 (7): 447 (1981)


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