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Chemistry

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Also known as: 111-42-2, 2,2'-iminodiethanol, Diolamine, Iminodiethanol, Bis(2-hydroxyethyl)amine, 2-(2-hydroxyethylamino)ethanol
Molecular Formula
C4H11NO2
Molecular Weight
105.14  g/mol
InChI Key
ZBCBWPMODOFKDW-UHFFFAOYSA-N
FDA UNII
AZE05TDV2V

Diethanolamine
Diethanolamine is a metabolite found in the aging mouse brain.
1 2D Structure

Diethanolamine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(2-hydroxyethylamino)ethanol
2.1.2 InChI
InChI=1S/C4H11NO2/c6-3-1-5-2-4-7/h5-7H,1-4H2
2.1.3 InChI Key
ZBCBWPMODOFKDW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(CO)NCCO
2.2 Other Identifiers
2.2.1 UNII
AZE05TDV2V
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Diethanolamine Acetate

2. Diethanolamine Bisulfate

3. Diethanolamine Fumarate

4. Diethanolamine Hydrochloride

5. Diethanolamine Maleate

6. Diethanolamine Maleate (1:1)

7. Diethanolamine Phosphate

8. Diethanolamine Sulfate (1:1)

9. Diethanolamine Sulfate (2:1)

10. Diethanolamine Sulfite

11. Diethanolamine Sulfite (1:1)

12. Diethanolammonium Sulfate

2.3.2 Depositor-Supplied Synonyms

1. 111-42-2

2. 2,2'-iminodiethanol

3. Diolamine

4. Iminodiethanol

5. Bis(2-hydroxyethyl)amine

6. 2-(2-hydroxyethylamino)ethanol

7. 2,2'-dihydroxydiethylamine

8. Diethylolamine

9. Ethanol, 2,2'-iminobis-

10. N,n-diethanolamine

11. Diethanolamin

12. 2,2'-iminobisethanol

13. 2,2'-azanediyldiethanol

14. Di(2-hydroxyethyl)amine

15. N,n'-iminodiethanol

16. Niax Deoa-lf

17. Bis(hydroxyethyl)amine

18. Diaethanolamin

19. Dabco Deoa-lf

20. N,n-bis(2-hydroxyethyl)amine

21. 2,2'-iminodi-1-ethanol

22. N,n-di(hydroxyethyl)amine

23. 2-[(2-hydroxyethyl)amino]ethan-1-ol

24. Nci-c55174

25. H2dea

26. Diolamine [inn]

27. Di(beta-hydroxyethyl)amine

28. 2,2'iminobisethanol

29. Mfcd00002843

30. Bis-2-hydroxyethylamine

31. 61791-44-4

32. Diethylamine, 2,2'-dihydroxy-

33. Poe (2) Tallow Amine

34. 2,2'-iminobis[ethanol]

35. 2-[(2-hydroxyethyl)amino]ethanol

36. Ethanol, 2,2'-iminodi-

37. Nsc 4959

38. Tegoamin Deoa 85

39. Diethanolamine (nf)

40. Diethanolamine [nf]

41. Dihydroxyethyl Tallowamine Oxide

42. Nsc-4959

43. Aze05tdv2v

44. Bis-(2-hydroxy-ethyl)-amine

45. 61791-46-6

46. Chebi:28123

47. Bis(2-hydroxyethyl)tallow Amine Oxide

48. Bis-(2-hydroxyethyl)-tallowamine Oxide

49. Dsstox_cid_1932

50. Dsstox_rid_76411

51. Diolamine (van)

52. Dsstox_gsid_21932

53. Amine,diethyl,2,2'-dihydroxy Diethanolamine

54. Diethanolamin [czech]

55. Diaethanolamin [german]

56. Cas-111-42-2

57. Ccris 5906

58. Hsdb 924

59. Einecs 203-868-0

60. Unii-aze05tdv2v

61. Brn 0605315

62. Diethanolarnine

63. Diethanol Amine

64. Aliphatic Amine

65. Ai3-15335

66. 2,2'-iminobis

67. Diethanolamine, 99%

68. Ethanol,2'-iminodi-

69. N, N-diethanol Amine

70. Ethanol,2'-iminobis-

71. 2, 2'-iminodiethanol

72. Amines, Tallow Alkyl Dihydroxyethyl, Oxides

73. Bis-(2-hydroxyethyl)amine

74. Bmse000371

75. Diolamine [mart.]

76. Diethanol, 2,2'-imino-

77. Diethanolamine [ii]

78. Diethanolamine [mi]

79. Ec 203-868-0

80. Diethylamine,2'-dihydroxy-

81. Schembl2324

82. Bis-(2-hydroxyethyl)-amine

83. Nciopen2_008991

84. Wln: Q2m2q

85. (hoch2 Ch2)2nh

86. Diethanolamine [hsdb]

87. Diethanolamine [iarc]

88. Diethanolamine [inci]

89. Ghl.pd_mitscher_leg0.542

90. 4-04-00-01514 (beilstein Handbook Reference)

91. Bis-(2-hydroxy-ethyl) Amine

92. Ethanol, 2,2'-iminobis-, N-tallow Alkyl Derivs.

93. Mls001065608

94. Bidd:gt0277

95. Diethanolamine [vandf]

96. Bis(2-hydroxyethyl)tallowamine

97. Diethanolamine, Lr, >=98%

98. Chembl119604

99. Schembl5200828

100. Diethanolamine [usp-rs]

101. Dtxsid3021932

102. 2-(2-hydroxy-ethylamino)ethanol

103. 2-(2-hydroxyethylamino)-ethanol

104. Diethanolamine, Biochemical Grade

105. Nsc4959

106. 2,2'-azanediylbis(ethan-1-ol)

107. Diethanolamine, Acs Reagent Grade

108. 2-(2-hydroxy-ethylamino)-ethanol

109. Diethanolamine, Analytical Standard

110. Diethanolamine, Puriss., 99.0%

111. Hms2269d18

112. Str03965

113. Zinc5975487

114. Tox21_201701

115. Tox21_300034

116. Diethanolamine, Bioxtra, >=98.5%

117. Stl264122

118. Akos000119884

119. Tallow Bis-(2-hydroxyethyl)amine Oxide

120. Diethanolamine Reagent Grade 1kg

121. Diethanolamine, Acs Reagent, >=98.5%

122. Ncgc00091478-01

123. Ncgc00091478-02

124. Ncgc00091478-03

125. Ncgc00091478-04

126. Ncgc00254061-01

127. Ncgc00259250-01

128. Diethanolamine, Reagent Grade, >=98.0%

129. Smr000112130

130. Trolamine Impurity B [ep Impurity]

131. Diethanolamine, Bioultra, >=99.5% (gc)

132. Diethanolamine, Saj First Grade, >=98.0%

133. Ft-0624757

134. I0008

135. S0376

136. Diethanolamine, Jis Special Grade, >=99.0%

137. C06772

138. D02337

139. D92250

140. Diethanolamine 1000 Microg/ml In Acetonitrile

141. 2,2'-iminobisethanol, N-tallow Alkyl, N-oxide

142. Q418437

143. Ethanol, 2,2'-iminobis-, N-tallow Alkyl, N-oxide

144. J-506841

145. F2190-0311

146. Z966690660

147. Bfc20619-2edf-4764-8e91-830aa892bd39

148. Ethanol, 2,2'-iminobis-, N-tallow Alkyl Derivs, N-oxides

149. Diethanolamine, Puriss. P.a., Acs Reagent, >=99.0% (gc)

150. Diethanolamine, United States Pharmacopeia (usp) Reference Standard

151. Trolamine Impurity B, European Pharmacopoeia (ep) Reference Standard

152. Diethanolamine, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 105.14 g/mol
Molecular Formula C4H11NO2
XLogP3-1.4
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass105.078978594 g/mol
Monoisotopic Mass105.078978594 g/mol
Topological Polar Surface Area52.5 Ų
Heavy Atom Count7
Formal Charge0
Complexity28.9
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Minimum/Potential Fatal Human Dose

The estimated fatal dose of diethanolamine in humans is 20 g.

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. 406


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

(14)C-Diethanolamine (7 mg/kg bw) was given orally to male Fischer 344 rats once or by daily repeat dosing for up to eight weeks. Single oral doses (0.7-200 mg/kg bw) were well absorbed but excreted very slowly. About 20-30% of oral and intravenous doses (7 mg/kg bw) was found in urine (mainly as unchanged diethanolamine), with less than 3% in feces and only 0.2% or less was exhaled (CO2) within 48 h. Most of the diethanolamine was retained in tissues at high concentrations. The tissue-to-blood ratios were 150-200 for the liver and kidney, 30-40 for the lung and spleen and 10-20 for the heart, brain and muscle. Tissue radioactivity was found mainly in aqueous extracts (up to 90%) and 5-10% was organic-extractable.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V77 364 (2000)


(14)C-Diethanolamine was applied to 19.5 sq cm of the dorsal skin (20 mg/sq cm, 1500 mg/kg bw) and covered for 48 hr (no washing) or for 6 hr before it was removed by washing. Absorbed (14)C-diethanolamine was determined in 48-hr urine and feces and from sampled tissues. Unwashed rats absorbed 1.4% and washed animals 0.64% of the dose, while the majority of (14)C-diethanolamine was recovered in the occlusive wrappings (80%) and in skin of the dose site (3.6%). The radioactivity was found in carcass, liver or kidneys but very little in urine (0.11%), feces or blood

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V77 363 (2000)


Studies of the penetration of (14)C-diethanolamine from cosmetic formulations (shampoos hair dyes and body lotions) through human skin samples indicated that approximately 0.1% of the applied dose of shampoo and hair dye formulations was absorbed into the receptor fluid after 5-30 minutes; in a 72-hour repeated dose study with a body lotion formulation, nearly 30% of applied diethanolamine accumulated in the skin and approximately 1% was absorbed into the receptor fluid.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V101 128 (2012)


Dermal absorption of diethanolamine is suggested to occur in rats since N-nitrosodiethanolamine was excreted in the urine of male Sprague-Dawley rats which had been administered diethanolamine by dermal application and given nitrite in their drinking water.

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. 403


5.2 Metabolism/Metabolites

Treatment of Wistar or Sherman rats with diethanolamine caused increases in the formation of hepatic phospholipids. In addition, dietary administration led to incorporation of ethanolamine into hepatic phospholipids, and repeated oral administration of diethanolamine in drinking water (one to three wk) at a dose of 320 mg/kg/day was found to reduce the level of incorporation of ethanolamine and choline into hepatic and renal phospholipids in Sprague-Dawley rats.

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. 403


Dermal absorption of diethanolamine is suggested to occur in rats since N-nitrosodiethanolamine was excreted in the urine of male Sprague-Dawley rats which had been administered diethanolamine by dermal application and given nitrite in their drinking water.

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. 403


Diethanolamine is known to be incorporated into membrane phospholipids. It can be O-phosphorylated and N-methylated to metabolites that are incorporated into polar head groups as aberrant membrane phospholipids (phosphoglyceride and sphingomyelin analogues) via the ethanolamine metabolic pathway.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V101 129 (2012)


After a single intravenous or oral administration of diethanolamine, rats predomnantly excreted the parent compound in the urine; after repeated oral administration, the parent compound was still the major product excreted in the urine but N-methylated metabolites were also detected. The parent compound also accounted for the majority of radioactivity extracted from the liver and brain of rats administered (14)C-diethanolamine; two minor metabolites identified in tissues were N-methyldiethanolamine and N,N-dimethyldiethanolamine.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V101 129 (2012)


5.3 Mechanism of Action

Diethanolamine (DEA) is a widely used ingredient in many consumer products and in a number of industrial applications. It has been previously reported that dermal administration of DEA to mice diminished hepatic stores of choline and altered brain development in the fetus. The aim of this study was to use mouse neural precursor cells in vitro to assess the mechanism underlying the effects of DEA. Cells exposed to DEA treatment (3mM) proliferated less (by 5-bromo-2-deoxyuridine incorporation) at 48 hr (24% of control [CT]), and had increased apoptosis at 72 hr (308% of CT). Uptake of choline into cells was reduced by DEA treatment (to 52% of CT), resulting in diminished intracellular concentrations of choline and phosphocholine (55 and 12% of CT, respectively). When choline concentration in the growth medium was increased threefold (to 210 uM), the effects of DEA exposure on cell proliferation and apoptosis were prevented, however, intracellular phosphocholine concentrations remained low. In choline kinase assays, we observed that DEA can be phosphorylated to phospho-DEA at the expense of choline. Thus, the effects of DEA are likely mediated by inhibition of choline transport into neural precursor cells and by altered metabolism of choline. /This/ study/ suggests that prenatal exposure to DEA may have a detrimental effect on brain development.

PMID:17204582 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2430108 Niculescu MD et al; Toxicol Sci. 96(2):321-6 (2007).


Diethanolamine increased the incidence and multiplicity of liver tumors in the mouse following chronic exposure. Diethanolamine is known to inhibit cellular choline uptake. Since choline deficiency produces tumors in rodents, diethanolamine, through choline depletion, may result in tumor development in rodents. The potential for diethanolamine to function through this mode of action in humans is not known. The present studies examined the effect of diethanolamine (0-500 mug/mL) and choline depletion on DNA synthesis and changes in expression of genes involved in cell growth pathways in primary cultures of mouse, rat, and human hepatocytes. In mouse and rat hepatocytes DNA synthesis was increased following treatment with 10 mug/mL diethanolamine and higher (3- to 4-fold over control). In contrast, diethanolamine failed to increase DNA synthesis in human hepatocytes. Incubation of hepatocytes in medium containing reduced choline (1/10 to 1/100 of normal medium; 0.898 to 0.0898 mg/L vs. 8.98 mg/L) increased DNA synthesis (1.6- and 1.8-fold of control in mouse and rat hepatocytes, respectively); however, choline depletion did not induce DNA synthesis in human hepatocytes. Mouse and rat hepatocytes incubated in medium supplemented with 2- to 50-fold excess choline reduced diethanolamine-induced DNA synthesis to control levels or below. Gene expression analysis of mouse and rat hepatocytes following diethanolamine treatment showed increases in genes associated with cell growth and decreases in expression of genes involved in apoptotic pathways. These results support the hypothesis that choline depletion is central to the mode of action for the induction of rodent hepatic neoplasia by diethanolamine. Furthermore, since diethanolamine treatment or choline depletion failed to induce DNA synthesis in human hepatocytes, these results suggest that humans may not be at risk from the carcinogenic effects of diethanolamine.

PMID:16014740 Kamendulis LM et al; Toxicol Sci 87 (2): 328-36 (2005)


Diethanolamine which interferes with phospholipid metab produced a loss of mitochondrial integrity after subacute admin to Sprague-Dawley rats.

PMID:442087 Barbee SJ, Hartung R; Toxicol Appl Pharmacol 47 (3): 431-40 (1979)


Diethanolamine inhibited in vitro synthesis of phosphatidyl choline and phosphatidyl ethanolamine in rat liver tissue.

PMID:442086 Barbee SJ, Hartung R; Toxicol Appl Pharmacol 47 (3): 431-40 (1979)


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ABOUT THIS PAGE

Looking for 111-42-2 / Diethanolamine API manufacturers, exporters & distributors?

Diethanolamine manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Diethanolamine API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Diethanolamine manufacturer or Diethanolamine supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Diethanolamine manufacturer or Diethanolamine supplier.

PharmaCompass also assists you with knowing the Diethanolamine API Price utilized in the formulation of products. Diethanolamine API Price is not always fixed or binding as the Diethanolamine Price is obtained through a variety of data sources. The Diethanolamine Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Diethanolamine

Synonyms

111-42-2, 2,2'-iminodiethanol, Diolamine, Iminodiethanol, Bis(2-hydroxyethyl)amine, 2-(2-hydroxyethylamino)ethanol

Cas Number

111-42-2

Unique Ingredient Identifier (UNII)

AZE05TDV2V

About Diethanolamine

Diethanolamine is a metabolite found in the aging mouse brain.

Diethanolamine Manufacturers

A Diethanolamine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Diethanolamine, including repackagers and relabelers. The FDA regulates Diethanolamine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Diethanolamine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Diethanolamine Suppliers

A Diethanolamine supplier is an individual or a company that provides Diethanolamine active pharmaceutical ingredient (API) or Diethanolamine finished formulations upon request. The Diethanolamine suppliers may include Diethanolamine API manufacturers, exporters, distributors and traders.

click here to find a list of Diethanolamine suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Diethanolamine USDMF

A Diethanolamine DMF (Drug Master File) is a document detailing the whole manufacturing process of Diethanolamine active pharmaceutical ingredient (API) in detail. Different forms of Diethanolamine DMFs exist exist since differing nations have different regulations, such as Diethanolamine USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Diethanolamine DMF submitted to regulatory agencies in the US is known as a USDMF. Diethanolamine USDMF includes data on Diethanolamine's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Diethanolamine USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Diethanolamine suppliers with USDMF on PharmaCompass.

Diethanolamine GMP

Diethanolamine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Diethanolamine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Diethanolamine GMP manufacturer or Diethanolamine GMP API supplier for your needs.

Diethanolamine CoA

A Diethanolamine CoA (Certificate of Analysis) is a formal document that attests to Diethanolamine's compliance with Diethanolamine specifications and serves as a tool for batch-level quality control.

Diethanolamine CoA mostly includes findings from lab analyses of a specific batch. For each Diethanolamine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Diethanolamine may be tested according to a variety of international standards, such as European Pharmacopoeia (Diethanolamine EP), Diethanolamine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Diethanolamine USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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