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Chemistry

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Also known as: 2-aminoethanol, Monoethanolamine, 141-43-5, Colamine, Aminoethanol, 2-hydroxyethylamine
Molecular Formula
C2H7NO
Molecular Weight
61.08  g/mol
InChI Key
HZAXFHJVJLSVMW-UHFFFAOYSA-N
FDA UNII
5KV86114PT

Ethanolamine
A viscous, hygroscopic amino alcohol with an ammoniacal odor. It is widely distributed in biological tissue and is a component of lecithin. It is used as a surfactant, fluorimetric reagent, and to remove CO2 and H2S from natural gas and other gases.
Ethanolamine is a Sclerosing Agent. The mechanism of action of ethanolamine is as a Sclerosing Activity. The physiologic effect of ethanolamine is by means of Vascular Sclerosing Activity.
1 2D Structure

Ethanolamine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-aminoethanol
2.1.2 InChI
InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2
2.1.3 InChI Key
HZAXFHJVJLSVMW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(CO)N
2.2 Other Identifiers
2.2.1 UNII
5KV86114PT
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2 Aminoethanol

2. 2-aminoethanol

3. Colamine

4. Monoethanolamine

2.3.2 Depositor-Supplied Synonyms

1. 2-aminoethanol

2. Monoethanolamine

3. 141-43-5

4. Colamine

5. Aminoethanol

6. 2-hydroxyethylamine

7. Glycinol

8. Olamine

9. 2-aminoethan-1-ol

10. 2-amino-1-ethanol

11. Ethanol, 2-amino-

12. Ethylolamine

13. Beta-hydroxyethylamine

14. 2-hydroxyethanamine

15. 1-amino-2-hydroxyethane

16. 2-aminoethyl Alcohol

17. Beta-aminoethyl Alcohol

18. Aethanolamin

19. 2-ethanolamine

20. Thiofaco M-50

21. Beta-aminoethanol

22. 2-amino-ethanol

23. Mea (alcohol)

24. Beta-ethanolamine

25. Kolamin [czech]

26. Usaf Ek-1597

27. Kolamin

28. Monoaethanolamin

29. Aethanolamin [german]

30. Caswell No. 426

31. Etanolamina [italian]

32. 2-aminoaethanol

33. 2-amino Ethanol

34. Monoaethanolamin [german]

35. 2-aminoaethanol [german]

36. 2-aminoetanolo [italian]

37. Glycinol (monoethanolamine)

38. Un2491

39. Ccris 6260

40. Hsdb 531

41. Ai3-24219

42. Olamine [inn]

43. Epa Pesticide Chemical Code 011601

44. Acid Orange 86

45. Ethanol Amine

46. Chebi:16000

47. Mfcd00008183

48. C.i. Acid Orange 108

49. Chembl104943

50. 12220-07-4

51. Ethanol, 2-amino-, Homopolymer

52. Envision Conditioner Pdd 9020

53. 5kv86114pt

54. Ethanol-amine

55. Un 2491

56. Monoethanolamine (nf)

57. Monoethanolamine [nf]

58. Ncgc00090789-02

59. 12220-09-6

60. 2-aminoethanol (ethanolamine)

61. 2-aminoethanol Reagent Acs Grade

62. Etanolamina

63. Ethanolamine Or Ethanolamine Solutions [un2491] [corrosive]

64. 2-aminoetanolo

65. Monoethanol Amine

66. 26778-51-8

67. Einecs 205-483-3

68. Ethanolamin

69. Ethanolarnine

70. Hydoxyethylamine

71. B-aminoethanol

72. B-ethanolamine

73. Unii-5kv86114pt

74. H-glycinol

75. 2 -aminoethanol

76. B-hydroxyethylamine

77. Ethanol, 2-amino

78. 2-hydroxylethylamine

79. H-gly-ol

80. .beta.-aminoethanol

81. .beta.-ethanolamine

82. B-aminoethyl Alcohol

83. Ethanolamine Solution

84. 2-hydroxy-ethylamine

85. 2-hydroxyethyl Amine

86. 2-hydroxyethyl-amine

87. 2-amino-ethan-1-ol

88. 2-hydroxy- Ethylamine

89. Ethanolamine Or Ethanolamine Solutions [un2491] [corrosive]

90. 2-hydroxy-1-ethylamine

91. .beta.-hydroxyethylamine

92. Ethanolamine, >=98%

93. Ethanolamine, >=99%

94. Ethanolamine [mi]

95. Nh2ch2ch2oh

96. .beta.-aminoethyl Alcohol

97. Dsstox_cid_2000

98. Ethanolamine, Ar, 99%

99. Bmse000276

100. Epitope Id:120354

101. Nh2c2h4oh

102. Ec 205-483-3

103. Ethanolamine [hsdb]

104. Ethanolamine [inci]

105. 2-aminoethanol, Redistilled

106. 2-aminoethanol,hydrochloride

107. Dsstox_rid_76452

108. Mea-lci; Mea 90

109. Dsstox_gsid_22000

110. Ethanolamine: 2-aminoethanol

111. Monoethanolamine [ii]

112. Bidd:er0367

113. Ethanolamine [who-dd]

114. Ethanolamine, Lr, >=99%

115. Bdbm7973

116. Dtxsid6022000

117. Ethanolamine, Analytical Standard

118. Monoethanolamine [usp-rs]

119. Ethanol, 2-amino- (8ci,9ci)

120. Ethanolamine [ep Monograph]

121. Str00417

122. Zinc8214617

123. Tox21_400020

124. C0594

125. Stl199164

126. Ethanolamine Or Ethanolamine Solutions

127. Ethanolamine, For Synthesis, 99.0%

128. Akos000245055

129. Db03994

130. 1h-indole-5-carbothioicacidamide

131. Ethanolamine, Acs Reagent, >=99.0%

132. Ethanolamine, Reagentplus(r), >=99%

133. Ethanolamine, Usp, 98.0-100.5%

134. Beta-aminoethyl Alcohol Beta-ethanolamine

135. Ncgc00090789-01

136. Ncgc00090789-03

137. Bp-21017

138. Bp-24368

139. Bp-31055

140. Cas-141-43-5

141. Trolamine Impurity A [ep Impurity]

142. Ethanolamine, Saj First Grade, >=99.0%

143. Ifosfamide Impurity D [ep Impurity]

144. A0297

145. Ethanolamine, Jis Special Grade, >=99.0%

146. Ft-0777922

147. En300-19392

148. 2-aminoethanol 1000 Microg/ml In Acetonitrile

149. C00189

150. D05074

151. P20022

152. A902308

153. Q410387

154. Ethanolamine, Purified By Redistillation, >=99.5%

155. J-508043

156. 587ce5aa-008a-469c-ab39-82cc4d0ca779

157. Ethanolamine; 2-aminoethanol; 2-aminoethyl Alcohol; Mea

158. F2190-0367

159. Ethanolamine, Puriss. P.a., Acs Reagent, >=99.0% (gc/nt)

160. Ethanolamine, Liquid, Bioreagent, Suitable For Cell Culture, >=98%

161. Trolamine Impurity A, European Pharmacopoeia (ep) Reference Standard

162. Ethanolamine Solution, For Peptide Synthesis, ~74% (t), ~70% In Methanol

163. Monoethanolamine, United States Pharmacopeia (usp) Reference Standard

164. Monoethanolamine, Pharmaceutical Secondary Standard; Certified Reference Material

165. Ethanolamine, Pharmagrade, Usp/nf, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 61.08 g/mol
Molecular Formula C2H7NO
XLogP3-1.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass61.052763847 g/mol
Monoisotopic Mass61.052763847 g/mol
Topological Polar Surface Area46.2 Ų
Heavy Atom Count4
Formal Charge0
Complexity10
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 FDA Pharmacological Classification
4.1.1 Active Moiety
ETHANOLAMINE
4.1.2 FDA UNII
5KV86114PT
4.1.3 Pharmacological Classes
Physiologic Effects [PE] - Vascular Sclerosing Activity
4.2 Absorption, Distribution and Excretion

The principal route of exposure is through skin, with some exposure occurring by inhalation of vapor and aerosols. Monoethanolamine (MEA), diethanolamine (DEA), and triethanolamine (TEA) in water penetrate rat skin at the rate of 2.9 x 10(-3), 4.36 x 10(-3) and 18 x 10(-3) cm/hr, respectively. MEA, DEA, and TEA are water-soluble ammonia derivatives, with pHs of 9-11 in water and pHa values of 9.3, 8.8, and 7.7, respectively.

PMID:8956558 Knaak JB et al; Rev Environ Contam Toxicol 149: 1-86 (1997)


The excretion rate in men was found to vary between 4.8 and 22.9 mg/day with a mean of 0.162 mg/kg /body weight/. 11 women were observed to excrete larger amounts, varying between 7.7 and 34.9 mg/day with a mean excretion rate of 0.492 mg/kg/day. The excretion rates in animals were approximately, for cats, 0.47 mg/kg/day; for rats, 1.46 mg/kg/day; and for rabbits, 1.0 mg/kg/day. From 6-47% of monoethanolamine administered to rats can be recovered in the urine.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V4 782


Persistence of low levels of radioactivity in dog whole blood was obtained after admin of (14)C-labeled ethanolamine. Excretion of radioactivity as % of dose in dog urine was 11. After 24 hr total blood radioactivity as % of dose was 1.69.

Rhodes C, Case DE; Xenobiotica 7 (1-2): 112 (1977)


/Ethanolamine/ is a normal urine constituent in man, excreted at a rate of 5-23 mg/day ... 40 percent of an administered dose is deaminated and excreted as urea.

Zenz, C., O.B. Dickerson, E.P. Horvath. Occupational Medicine. 3rd ed. St. Louis, MO., 1994, p. 707


For more Absorption, Distribution and Excretion (Complete) data for 2-AMINOETHANOL (10 total), please visit the HSDB record page.


4.3 Metabolism/Metabolites

Ethanolamine can be used as a source of carbon and nitrogen by phylogenetically diverse bacteria. Ethanolamine-ammonia lyase, the enzyme that breaks ethanolamine into acetaldehyde and ammonia, is encoded by the gene tandem eutBC. Despite extensive studies of ethanolamine utilization in Salmonella enterica serovar Typhimurium, much remains to be learned about EutBC structure and catalytic mechanism, about the evolutionary origin of ethanolamine utilization, and about regulatory links between the metabolism of ethanolamine itself and the ethanolamine-ammonia lyase cofactor adenosylcobalamin. We used computational analysis of sequences, structures, genome contexts, and phylogenies of ethanolamine-ammonia lyases to address these questions and to evaluate recent data-mining studies that have suggested an association between bacterial food poisoning and the diol utilization pathways. We found that EutBC evolution included recruitment of a TIM barrel and a Rossmann fold domain and their fusion to N-terminal alpha-helical domains to give EutB and EutC, respectively. This fusion was followed by recruitment and occasional loss of auxiliary ethanolamine utilization genes in Firmicutes and by several horizontal transfers, most notably from the firmicute stem to the Enterobacteriaceae and from Alphaproteobacteria to Actinobacteria. We identified a conserved DNA motif that likely represents the EutR-binding site and is shared by the ethanolamine and cobalamin operons in several enterobacterial species, suggesting a mechanism for coupling the biosyntheses of apoenzyme and cofactor in these species. Finally, we found that the food poisoning phenotype is associated with the structural components of metabolosome more strongly than with ethanolamine utilization genes or with paralogous propanediol utilization genes per se.

PMID:19783625 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2786565 Tsoy O et al; J Bacteriol 191 (23): 7157-64 (2009)


Forty percent of (15)N-labeled ethanolamine appears as urea within 24 hr when it is given to rabbits, suggesting that it is deaminated. In rat liver homogenates, ethanolamine undergoes demethylation yielding formaldehyde.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V4 782


Ethanolamine is a normal intermediate in the metabolism of some animal species, having a part in the formation of phospholipids and choline.

American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 2


The distribution and metabolism of topical (14)C ethanolamine was studied in vivo, using athymic nude mice, human skin grafted onto athymic nude mice, and in vitro, using excised pig skin. Ethanolamine was the only radioactive phospholipid base detected in the human skin grafts, in the mouse skin, and in the pig skin. Ethanolamine that penetrated human skin grafts or mouse skin was extensively metabolized in the animal. The liver is a major site for metabolism of ethanolamine, containing over 24% of the applied radioactive dose. The kidneys, lungs, brain, and the heart contained 2.53, 0.55, 0.27, and 0.15% of the dose, respectively. Hepatic, human skin graft, and mouse skin proteins were also highly radioactive. Over 18% of the topical radioactive dose oxidized to (14)CO2 and 4.6% was excreted in the urine over 24 hr. Urea, glycine, serine, choline, and uric acid were the urinary metabolites of ethanolamine.

Klain GJ et al; Fundam Appl Toxicol 5 (6 Pt 2): S127-33 (1985)


For more Metabolism/Metabolites (Complete) data for 2-AMINOETHANOL (10 total), please visit the HSDB record page.


4.4 Biological Half-Life

The half-life of the persistent low level of radioactivity in the blood /of dogs administered 14C-ethanolamine/ was 19 days.

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. 426


Labeled MEA was administered to dogs. ... After 24 hr ... the half-life was 19 days.

Christian M, ed; J American College of Toxicology 2 (7): 183-226 (1983)


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01-Jan-2022
31-Oct-2025
KGS
overview