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Chemistry

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Also known as: Ether, Ethyl ether, Ethoxyethane, 60-29-7, Ethyl oxide, Pronarcol
Molecular Formula
C4H10O
Molecular Weight
74.12  g/mol
InChI Key
RTZKZFJDLAIYFH-UHFFFAOYSA-N
FDA UNII
0F5N573A2Y

Diethyl Ether
A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.
1 2D Structure

Diethyl Ether

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
ethoxyethane
2.1.2 InChI
InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3
2.1.3 InChI Key
RTZKZFJDLAIYFH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCOCC
2.2 Other Identifiers
2.2.1 UNII
0F5N573A2Y
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ether

2. Ether, Diethyl

3. Ether, Ethyl

4. Ethyl Ether

2.3.2 Depositor-Supplied Synonyms

1. Ether

2. Ethyl Ether

3. Ethoxyethane

4. 60-29-7

5. Ethyl Oxide

6. Pronarcol

7. Diethyl Oxide

8. Aether

9. Anesthetic Ether

10. Anaesthetic Ether

11. Diethylether

12. Solvent Ether

13. 3-oxapentane

14. Ether, Ethyl

15. Diaethylaether

16. Dwuetylowy Eter

17. Ether Ethylique

18. Etere Etilico

19. Ethane, 1,1'-oxybis-

20. Oxyde D'ethyle

21. 1,1'-oxybisethane

22. Anesthesia Ether

23. 1,1'-oxydiethane

24. Ethyl Ether, Tech.

25. Diethylaether

26. Sulfuric Ether

27. Aether Pro Narcosi

28. Rcra Waste Number U117

29. Etherum

30. Nsc 100036

31. Nsc-100036

32. Chebi:35702

33. 0f5n573a2y

34. (c2h5)2o

35. Mfcd00011646

36. Ethyl Ether Anhydrous

37. Ether [jan]

38. Diaethylaether [german]

39. Etere Etilico [italian]

40. Dwuetylowy Eter [polish]

41. Ether Ethylique [french]

42. Oxyde D'ethyle [french]

43. Ether, Diethyl

44. Hsdb 70

45. Et2o

46. Ether [usp:jan]

47. Ether, Anhydrous

48. Einecs 200-467-2

49. Un1155

50. Rcra Waste No. U117

51. Dietylether

52. Diethyether

53. Di Ethylether

54. Di-ethylether

55. Diehtyl Ether

56. Diethyl-ether

57. Ether Anhydrous

58. Ethoxy-ethane

59. Monoethyl Ether

60. Anhydrous Ether

61. Diethl Ether

62. Diethy Ether

63. Dietyl Ether

64. Ehtyl Ether

65. Ethyl-ether

66. Diethyi Ether

67. Diethyl Ester

68. Unii-0f5n573a2y

69. 2-ethoxyethane

70. Ai3-24233

71. Di Ethyl Ether

72. Di-ethyl Ether

73. Ethyl Ether-

74. Alcohols, C7-21, Ethoxylated

75. Alcohols, C8-22, Ethoxylated

76. Alcohols, C14-26, Ethoxylated

77. Alcohols, C16-22, Ethoxylated

78. Etoet

79. Ether Anaesthesicus

80. 1-ethoxyethane #

81. Amines, C20-22-alkyl, Ethoxylated

82. Ethane,1'-oxybis-

83. Diethyl Ether [anaesthetics, Volatile]

84. 1,1' -oxybisethane

85. 1,1'-oxy-bisethane

86. 1,1'-oxybis Ethane

87. Oet2

88. 1,1'-oxobis(ethane)

89. Etherum [hpus]

90. Ether [vandf]

91. Ether [hsdb]

92. Ether (jp17/usp)

93. Ether [ii]

94. Ethyl Ether [mi]

95. Ec 200-467-2

96. Diethyl Ether, Hplc Grade

97. Ethyl Ether [inci]

98. O(et)2

99. Diethyl Ether Or Ethyl Ether

100. Diethylether (peptide Grade)

101. Ether [ep Monograph]

102. Diethyl Ether, >=99.5%

103. Chembl16264

104. Ether [usp Monograph]

105. Ethyl Ether [who-dd]

106. Ethyl Ether Anhydrous A.c.s.

107. Solvent Ether [mart.]

108. O(ch2ch3)2

109. Wln: 2o2

110. Dtxsid3021720

111. Diethyl Ether, P.a., 99.0%

112. Diethyl Ether, P.a., 99.5%

113. Diethyl Ether, Analytical Standard

114. Anaesthetic Ether [who-ip]

115. O(c2h5)2

116. Zinc1657408

117. Nsc100036

118. Stl445704

119. Akos015950740

120. Diethyl Ether, Acs Reagent, 99.5%

121. Db13598

122. Diethyl Ether, Spectrophotometric Grade

123. Un 1155

124. 69013-19-0

125. 69227-20-9

126. 70131-58-7

127. 71011-10-4

128. Diethyl Ether, Purum, >=99.0% (gc)

129. Ether Anaesthesicus [who-ip Latin]

130. Diethylether 100 Microg/ml In Acetonitrile

131. D3479

132. Diethyl Ether, Saj First Grade, >=99.0%

133. Ft-0624836

134. Ft-0624837

135. Ft-0624838

136. Diethyl Ether, Jis Special Grade, >=99.5%

137. D01772

138. Diethyl Ether, Uv Hplc Spectroscopic, 99.9%

139. Diethyl Ether, Anhydrous, 99.5%, ?50 Ppm H2o

140. Ethyl Ether Anhydrous Stabilized With 5ppm Of Bht

141. Q202218

142. Diethyl Ether, Laboratory Reagent, >=99.5% (gc)

143. Diethyl Ether, For Hplc, >=99.9%, Inhibitor-free

144. Diethyl Ether, For Uv-spectroscopy, >=99.8% (gc)

145. 1-hydroperoxy-8-carboxyoctyl 3,4-epoxynon-(2e)-enyl Ether

146. Diethyl Ether Or Ethyl Ether [un1155] [flammable Liquid]

147. Diethyl Ether, Anhydrous, Acs, 99% Min, Stab. With Bht

148. Diethyl Ether, Puriss., 99.0%, Contains 0.0025% Bht

149. Diethyl Ether Anhydrous Acs Grade Stabilized With 5ppm Of Bht

150. Diethyl Ether, Puriss. P.a., Acs Reagent, >=99.8% (gc)

151. Diethyl Ether, Spectrophotometric Grade, 99%, Inhibitor Free

152. Ethyl Ether, Anhydrous, Stabilized With Bht, Max Water 50ppm

153. Diethyl Ether, Ar, Contains 5 Ppm Bht As Stabilizer, >=99.5%

154. Diethyl Ether, For Hplc, Contains 5 Ppm Bht As Stabilizer, >=99%

155. Diethyl Ether, For Residue Analysis, Suitable For 5000 Per Jis

156. Diethyl Ether, Lr, Contains 5 Ppm Bht As Stabilizer, >=99.5%

157. Diethyl Ether, P.a., Acs Reagent, 99.5%, Contains 0.0025% Bht

158. Diethyl Ether, Spectrophotometric Grade, >=99.9%, Inhibitor-free

159. Diethyl Ether, Acs Reagent, Anhydrous, >=99.0%, Contains Bht As Inhibitor

160. Diethyl Ether, Anhydrous, Acs Reagent, >=99.0%, Contains Bht As Inhibitor

161. Diethyl Ether, Anhydrous, Contains 5 Ppm Bht As Stabilizer, >=99.5%

162. Diethyl Ether, Contains 1 Ppm Bht As Inhibitor, Anhydrous, >=99.7%

163. Diethyl Ether, Suitable For 1000 Per Jis, >=99.5%, For Residue Analysis

164. Diethyl Ether, Suitable For 300 Per Jis, >=99.5%, For Residue Analysis

165. Diethyl Ether, Acs Reagent, >=98.0%, Contains ~2% Ethanol And ~10ppm Bht As Inhibitor

166. Diethyl Ether, Acs Reagent, Anhydrous, >=99.0%, Contains 1 Ppm Bht As Inhibitor

167. Diethyl Ether, Anhydrous, Acs Reagent, >=99.0%, Contains 1 Ppm Bht As Inhibitor

168. Diethyl Ether, Pharmaceutical Secondary Standard; Certified Reference Material

169. Diethyl Ether, Puriss., Dried Over Molecular Sieve (h2o <=0.005%), >=99.8% (gc)

170. Diethyl Ether, Puriss., Meets Analytical Specification Of Ph.??eur., Bp, >=99.5% (gc)

171. Diethyl Ether, Reagent Grade, >=98%, Contains ~2% Ethanol And ~10ppm Bht As Inhibitor

172. 667919-88-2

173. 68890-94-8

174. 68890-95-9

175. Diethyl Ether, Contains Bht As Inhibitor, Puriss. P.a., Acs Reagent, Reag. Iso, Reag. Ph. Eur., >=99.8%

176. Diethyl Ether, Puriss., Dried Over Molecular Sieve Deperox Dehydrat (h2o <=0.005%), >=99.8% (gc)

177. Ethanol, 2,2',2''-nitrilotris-, Compds. With Polyethylene Glycol Mono-c12-18-alkyl Ethers Phosphates

178. Hexanedioic Acid, Polymer With 1,3-isobenzofurandione And 1,2-propanediol, Diesters With C8-18 And C18-unsatd. Fatty Acids

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 74.12 g/mol
Molecular Formula C4H10O
XLogP30.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Exact Mass74.073164938 g/mol
Monoisotopic Mass74.073164938 g/mol
Topological Polar Surface Area9.2 Ų
Heavy Atom Count5
Formal Charge0
Complexity11.1
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 Therapeutic Uses

Anesthetics, Inhalation; Solvents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Ether is sometimes injected intravenously as a measure of circulation time when evaluating a patient's cardiac status ... /SRP: Former use/

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-184


Ether, mixed with approximately 2 volumes of alcohol to form ether spirit /SRP: was formerly used/ as an orally administered preparation for treatment of gastric flatulence and milder forms of gastralgia.

Osol, A., and R. Pratt. (eds.). The United States Dispensatory. 27th ed. Philadelphia: J.B. Lippincott, 1973., p. 507


Intravenous administration of up to 1000 mL of a 2.5 to 7.5% solution of ether in isotonic sodium chloride solution and 5% dextrose solution has been /SRP: formerly/ employed to quiet manic patients.

Osol, A., and R. Pratt. (eds.). The United States Dispensatory. 27th ed. Philadelphia: J.B. Lippincott, 1973., p. 507


For more Therapeutic Uses (Complete) data for DIETHYL ETHER (11 total), please visit the HSDB record page.


4.2 Drug Warning

Main contraindications to ether anesthesia are acute and chronic respiratory diseases and advanced renal disease.

Di Palma, J. (ed.). Drill's Pharmacology in Medicine. 4th ed. New York: McGraw Hill Book Co., 1971., p. 507


The primary physiologic effect of ethyl ether is /CNS depression/ and general anesthesia. Concentrations of ethyl ether ranging from 100,000 to 150,000 ppm are required for induction of anesthesia; however, exposure at this concentration may produce fatalities due to respiratory arrest. Repeated exposures of workers in industry was often intentional, ether jags. Symptoms ... consist of loss of appetite, exhaustion, headache, sleepiness, dizziness, excitation, and psychic disturbances. Albuminuria ... and polycythemia may result.

American Conference of Governmental Industrial Hygienists, Inc. Documentation of the Threshold Limit Values and Biological Exposure Indices. 6th ed. Volumes I, II, III. Cincinnati, OH: ACGIH, 1991., p. 631


It irritates mucous membranes. Except for its use in small rodents, ether is usually not potent enough to avoid slow and difficult induction unless other premedication is employed.

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 193


4.3 Minimum/Potential Fatal Human Dose

Blood level: ... Lethal= 1400-1890 ug/mL

Winek, C.L. Drug and Chemical Blood-Level Data 1985. Pittsburgh, PA: Allied Fischer Scientific, 1985.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Solvents

Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant and Hackh's Chemical Dictionary, 5th ed) (See all compounds classified as Solvents.)


Anesthetics, Inhalation

Gases or volatile liquids that vary in the rate at which they induce anesthesia; potency; the degree of circulation, respiratory, or neuromuscular depression they produce; and analgesic effects. Inhalation anesthetics have advantages over intravenous agents in that the depth of anesthesia can be changed rapidly by altering the inhaled concentration. Because of their rapid elimination, any postoperative respiratory depression is of relatively short duration. (From AMA Drug Evaluations Annual, 1994, p173) (See all compounds classified as Anesthetics, Inhalation.)


5.2 ATC Code

N - Nervous system

N01 - Anesthetics

N01A - Anesthetics, general

N01AA - Ethers

N01AA01 - Diethyl ether


5.3 Absorption, Distribution and Excretion

After inhalation, ethyl ether is rapidly transferred from alveoli to blood. The normal alveolar membrane poses no barrier to the transfer of ethyl ether in either direction. The blood/gas distribution coefficient of ethyl ether is high - 12.1. For oil/gas, the distribution coefficient is 65. ...The penetration /of ethyl ether/ in rabbit skin /was studied/. ... Doses over 20 mL/kg bw could not be retained in contact with the skin. ... The single dermal penetration LD50 was greater than 20 mL/kg bw.

NIOSH; NEG and NIOSH Basis for an Occupational Health Standard for Ethyl Ether. p.5. Arbete och Halsa 30 (2002) Available from, as of October 31, 2007: https://www.cdc.gov/niosh/pdfs/93-103a.pdf


The majority of inhaled ethyl ether is excreted unchanged through the lungs. In experiments on dogs, /it was/ reported that the recovery of ethyl ether in expired air was 79-92% (average for 12 dogs 87%).

NIOSH; NEG and NIOSH Basis for an Occupational Health Standard for Ethyl Ether. p.7. Arbete och Halsa 30 (2002) Available from, as of October 31, 2007: https://www.cdc.gov/niosh/pdfs/93-103a.pdf


... Over 90% of it can be recovered in the exhaled air. A small fraction is excreted in the urine, milk, sweat and other body fluids, and a tiny amount escapes by diffusion through the intact skin. All volatile anesthetics easily pass placental barrier ...

Goodman, L.S., and A. G. Gilman. (eds.). The Pharmacological Basis of Therapeutics. 4th ed. New York: Macmillan Co., 1970., p. 82


Diethyl ether is instantaneously absorbed from inhaled air into the bloodstream, from which it passes rapidly into the brain. ... It is also taken up rapidly by fatty tissue in rats.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:880


For more Absorption, Distribution and Excretion (Complete) data for DIETHYL ETHER (15 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

It has been estimated that about 8-10% of absorbed ethyl ether is metabolized in the body whereas the remainder is excreted unchanged through the lungs. Ethyl ether is metabolized to ethanol and acetaldehyde by the inducible hepatic microsomal enzyme system, a cytochrome P450-containing monooxygenase system. Ethanol and acetaldehyde are rapidly oxidized to acetate, and the acetate subsequently enters the 2-carbon pool of intermediary metabolism.

NIOSH; NEG and NIOSH Basis for an Occupational Health Standard for Ethyl Ether. p.7. Arbete och Halsa 30 (2002) Available from, as of October 31, 2007: https://www.cdc.gov/niosh/pdfs/93-103a.pdf


When (14)C diethyl ether ... admin ... to mice by inhalation a proportion was rapidly metabolized into palmitic, stearic, & oleic acids & cholesterol, which, together with 3 other non-volatile radioactive metab ... mono-, di-, & tri-glycerides, were recovered from liver.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 257


Diethyl ether caused detectable blood acetaldehyde levels in 15 patients. Avg acetaldehyde concn was 21 umolar which approximates the level found after intake of ethanol.

PMID:7405692 MOERLAND ET AL; ADV EXP MED BIOL 126 (ISS BIOL EFF ALCOHOL): 453 (1980)


Liver microsomes metabolized diethyl ether to acetaldehyde. The reaction was NADPH-dependent, & inhibited by CO & antibody to rat liver cytochrome P450. Cytochrome P450 containing monooxygenase system analogous to o-dealkylation is indicated.

PMID:6767481 CHENGELIS & NEAL; BIOCHEM PHARMACOL 29 (2): 247 (1980)


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


5.5 Mechanism of Action

The mechanism of action by which .... ethyl ether produce/s/ reversible loss of consciousness is still unclear. Anesthesia can be produced by a wide variety of chemical agents, ranging from inert rare gases to steriodal molecules. This apparent lack of specificity, together with the observation that general anesthesia can be reversed by high pressure, poses a unique pharmacological problem. Most theories concern interaction of anesthetics with either membrane lipids or hydrophobic regions of specificic membrane-bound proteins. One hypothesis is that the anesthetic changes the function of an ion channel protein by modifying the conformation of the protein. Some investigators suggest that the GABA receptor may be the ion channel protein that is affected by inhalation of anesthetic agents... The most appropriate concept for the mechanism of general anesthesia /may be/ a the heterogenous site of anesthetic action, including both lipid and protein membrane components linked with neuronal function.

NIOSH; NEG and NIOSH Basis for an Occupational Health Standard for Ethyl Ether. p.8. Arbete och Halsa 30 (2002) Available from, as of October 31, 2007: https://www.cdc.gov/niosh/pdfs/93-103a.pdf


In chronically catheterized rats, diethyl ether increased plasma adrenaline and noradrenaline concentrations indicating that this drug stimulates both neurosympathetic and adrenomedullary functions. These effects appear to be centrally mediated, since ganglionic blockade or spinal transection completely counteracted the diethyl ether induced increases in plasma calcium levels.

PMID:3556398 Carruba MO et al; Eur J Pharmacol 134 (1): 15-24 (1987)


Hippocampal EEG signals derived from chronically implanted electrodes in the freely moving rat were recorded before and after administration of centrally acting drugs, and analyzed by power and coherence spectra. Diethyl ether induced a low frequency (3-6 c/s) theta power and coherence peak in the immobile rat, which was sensitive to atropine or scopolamine. The residue spectrum, defined as the EEG spectrum with the theta harmonics removed, was sensitive to centrally acting drugs. Diethyl ether suppressed fast waves of 50-100 c/s, and some conditions, enhanced 15-50 c/s waves.

PMID:2578356 Leung LW St; Electroencephalogr Clin Neurophysiol 60 (1): 65-77 (1985)


The plasma beta-endorphin responses to ether and handling stress were examined in animals of various ages. At each age studied there was a significant, stress-induced elevation of plasma beta-endorphin-like immunoreactivity levels were higher in animals 3,7, and 14 days of age than in adults.

PMID:2950969 Iny LJ et al; Brain Res 428 (2): 177-81 (1987)


Cortical action potential activity is suppressed by ether anesthesia and is not affected when sensory fibers in the sciatic nerve are stimulated. Consequently, ether blocks sensory pathways to the cortex; the blockade occurs even before cortical activity is entirely suspended. In contrast, pentobarbital suppresses activity in the cortex without blocking the sensory path to it during sciatic nerve stimulation.

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 192


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