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Also known as: 302-17-0, 2,2,2-trichloroethane-1,1-diol, Trichloroacetaldehyde hydrate, Noctec, Tosyl, Chloral monohydrate
Molecular Formula
C2H3Cl3O2
Molecular Weight
165.40  g/mol
InChI Key
RNFNDJAIBTYOQL-UHFFFAOYSA-N
FDA UNII
418M5916WG

Chloral Hydrate
A hypnotic and sedative used in the treatment of INSOMNIA.
1 2D Structure

Chloral Hydrate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,2,2-trichloroethane-1,1-diol
2.1.2 InChI
InChI=1S/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H
2.1.3 InChI Key
RNFNDJAIBTYOQL-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(C(Cl)(Cl)Cl)(O)O
2.2 Other Identifiers
2.2.1 UNII
418M5916WG
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Hydrate, Chloral

2. Noctec

2.3.2 Depositor-Supplied Synonyms

1. 302-17-0

2. 2,2,2-trichloroethane-1,1-diol

3. Trichloroacetaldehyde Hydrate

4. Noctec

5. Tosyl

6. Chloral Monohydrate

7. Chloraldurat

8. Phaldrone

9. Nycoton

10. Chloradorm

11. Chloralhydrate

12. Kessodrate

13. 1,1-ethanediol, 2,2,2-trichloro-

14. Cohidrate

15. Felsules

16. Lorinal

17. Oradrate

18. Rectules

19. Trawotox

20. Dormal

21. Escre

22. Hynos

23. Nycton

24. Somnos

25. Sontec

26. Knockout Drops

27. Somni Sed

28. Sk-chloral Hydrate

29. Aquachloral

30. Somnote

31. Trichloracetaldehyd-hydrat

32. Chlorali Hydras

33. 2,2,2-trichloro-1,1-ethanediol

34. Hydrate De Chloral

35. 1,1,1-trichloro-2,2-ethanediol

36. Trichloroacetaldehyde Monohydrate

37. Chloralhydrat

38. Hydral

39. 1,1,1-trichloro-2,2-dihydroxyethane

40. Bi 3411

41. Chloralum

42. Lycoral

43. Cloral Hydrate

44. Nsc 3210

45. Nsc-3210

46. Dtxsid7020261

47. Chebi:28142

48. 418m5916wg

49. Ncgc00159374-02

50. Ncgc00159374-03

51. Kloralhydrat

52. Chloralex

53. Chloralvan

54. Novochlorhydrate

55. Dsstox_cid_261

56. Dsstox_rid_75470

57. Dsstox_gsid_20261

58. Chloraldural [swiss]

59. Caswell No. 168

60. Chloraldurat [german]

61. Chloraldural

62. Nortec

63. Cas-302-17-0

64. Trichloroacetaldehyde, Hydrated

65. Ccris 4142

66. Hsdb 222

67. Aquachloral Supprettes

68. Trichloracetaldehyd-hydrat [german]

69. Einecs 206-117-5

70. Epa Pesticide Chemical Code 268100

71. Brn 1698497

72. Ai3-00082

73. Dea No. 2465

74. Ethanediol, 2,2,2-trichloro-

75. Unii-418m5916wg

76. Chloral Hydrate [usp:ban:jan]

77. Mfcd00044479

78. Noctec (tn)

79. 201612-49-9

80. Trichloroethanal Hydrate

81. Wln: Qyqxggg

82. Chloralum [hpus]

83. Chloral-[13c] Hydrate

84. 1, 2,2,2-trichloro-

85. Schembl34327

86. Chloral Hydrate [mi]

87. 4-01-00-03143 (beilstein Handbook Reference)

88. Chloral Hydrate [jan]

89. Chloral Hydrate (jp17/usp)

90. Chloral Hydrate [hsdb]

91. Chloral Hydrate [iarc]

92. Chembl455917

93. Chloral Hydrate [vandf]

94. Cloral Hydrate [mart.]

95. 2,2-trichloro-1,1-ethanediol

96. Chloral Hydrate [who-dd]

97. Chloral Hydrate [who-ip]

98. Nsc3210

99. Chloral Hydrate, P.a., 99.0%

100. Bcp31225

101. Zinc3872049

102. 1,1-trichloro-2,2-dihydroxyethane

103. Tox21_111614

104. Tox21_200110

105. Chloral Hydrate [green Book]

106. Stl445706

107. Chloral Hydrate [ep Impurity]

108. Akos009157238

109. Chloral Hydrate [ep Monograph]

110. Tox21_111614_1

111. Chloral Hydrate [usp Monograph]

112. Chlorali Hydras [who-ip Latin]

113. Db01563

114. Ncgc00159374-04

115. Ncgc00257664-01

116. Chloral Hydrate;2,2,2-trichloro-1,1-ethanediol;1,1-ethanediol, 2,2,2-trichloro-;choral Hydrate;2,2,2-trichloroethane-1,1-diol;2,2,2trichloroethane1,1diol

117. Ls-12935

118. Db-047727

119. Chloral Hydrate 1000 Microg/ml In Methanol

120. Chloral Hydrate, Saj First Grade, >=99.5%

121. Trichloro Acetaldehyde Hydrate Chloral Hydrate

122. C06899

123. Chloral Hydrate, Crystallized, >=98.0% (t)

124. Chloral Hydrate, Saj Special Grade, >=99.7%

125. Chloralhydrate 1000 Microg/ml In Acetonitrile

126. D00265

127. A936505

128. Q412340

129. J-520014

130. Q-200826

131. F0001-0929

132. 2,2,2-trichloroethane-1,1-diol;trichloroacetaldehyde Hydrate

133. Chloral Hydrate Solution, 1000 Mug/ml In Acetonitrile, Analytical Standard

134. Chloral Hydrate, Meets Analytical Specification Of Ph. Eur., Bp, Usp, 99.5-101%

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 165.40 g/mol
Molecular Formula C2H3Cl3O2
XLogP31
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass163.919862 g/mol
Monoisotopic Mass163.919862 g/mol
Topological Polar Surface Area40.5 Ų
Heavy Atom Count7
Formal Charge0
Complexity56.4
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

Sedatives, Nonbarbiturate; Anesthetics, Intravenous

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


Chloral hydrate also has been used as an adjunct to opiates and analgesics in postoperative care and control of pain. However, it generally has been replaced by agents with better pharmacokinetic and pharmacodynamic profiles. /Included in US product labeling/

USP. Convention. USPDI - Drug Information for the Health Care Professional. 20th ed. Volume I. Micromedex, Inc. Englewood, CO., 2000. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 859


Chloral hydrate has been used as a routine sedative. However, it generally has been replaced by safer and more effective agents. /Included in US product labeling/

USP. Convention. USPDI - Drug Information for the Health Care Professional. 20th ed. Volume I. Micromedex, Inc. Englewood, CO., 2000. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 859


Chloral hydrate has been used for the treatment of insomnia. However, this medication is effective as a hypnotic only for short-term use; it has been shown to lose its effectiveness for both inducing and maintaining sleep after 2 weeks of administration. In addition, chloral hydrate generally has been replaced by agents with better pharmacokinetic and pharmacodynamic profiles. /Included in US product labeling/

USP. Convention. USPDI - Drug Information for the Health Care Professional. 20th ed. Volume I. Micromedex, Inc. Englewood, CO., 2000. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 859


For more Therapeutic Uses (Complete) data for CHLORAL HYDRATE (13 total), please visit the HSDB record page.


4.2 Drug Warning

... /Chloral hydrate/ crosses the placenta and the effects of the drug on the fetus are unknown. The manufactures caution that the use of chloral hydrate durring pregnancy may cause withdrawal symptoms in neonates

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2610


Prolonged use of chloral hydrate may produce tolerance and physical and/or psychologic dependence. Tolerance and psychological dependence may develop by the second week of continued therapy.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2610


Cutaneous reactions to chloral hydrate are not common but have included scarlatiniform or erythematous rash, urticaria, angioedema, purpura, eczema, bullous lesions, and erythema multiforme. Sometimes cutaneous reactions have been accompanied by fever.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2609


Gastric irritation manifested by nausea, vomiting, and diarrhea is the most frequent adverse effect of oral chloral hydrate administration. Gastric irritation may be minimized by diluting the oral solution with water or other liquid or administering other oral dosage forms with liquids. Flatulence and unpleasant taste may also occur.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2609


For more Drug Warnings (Complete) data for CHLORAL HYDRATE (14 total), please visit the HSDB record page.


4.3 Minimum/Potential Fatal Human Dose

The lethal oral dose of chloral hydrate in adults is about 10 g; however, ingestion of 4 g has caused death, and some patients have survived ingestion of as much as 30 g.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2610


Lethal doses /of chloral hydrate/ are between 5 and 10 g.

Gossel, T.A., J.D. Bricker. Principles of Clinical Toxicology. 3rd ed. New York, NY: Raven Press, Ltd., 1994., p. 315


4.4 Drug Indication

Mainly used as a hypnotic in the treatment of insomnia; however, it is only effective as a hypnotic for short-term use. May be used as a routine sedative preoperatively to decrease anxiety and cause sedation and/or sleep with respiration depression or cough reflex.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Hypnotics and Sedatives

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)


5.2 ATC Code

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CC - Aldehydes and derivatives

N05CC01 - Chloral hydrate


5.3 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed in the GI tract following oral or rectal administration. Chloral hydrate and its active metabolite, trichloroethanol, have been detected in CSF, umbilical cord blood, fetal blood, and amniotic fluid.


Route of Elimination

Trichloroethanol, trichloroethanol glucuronide, and trichloroacetic acid are excreted in the urine. Some trichloroethanol glucuronide may be secreted into bile and excreted in the feces.


Following therapeutic doses of chloral hydrate, only small, clinically insignificant amounts of the active metabolite are distributed into milk.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2610


Chloral hydrate is rapidly absorbed from the GI tract following oral or rectal administration. Plasma concentrations of chloral hydrate (or the major metabolite, trichloroethanol) required for sedative or hypnotic effects are unknown. Following administration of a single chloral hydrate dose of 15 mg/kg, peak plasma concentrations of trichloroethanol ranged from 7-10 ug/mL in one study.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2610


After oral administration, chloral hydrate is rapidly absorbed from the gastrointestinal tract. Peak levels of trichloroethanol and trichloroethanol glucuronide were reached within 20- 60 min after oral administration of aqueous solutions.

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. V63 251 (1995)


The volume of distribution of chloral hydrate is 0.6 L/kg.

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 586


For more Absorption, Distribution and Excretion (Complete) data for CHLORAL HYDRATE (11 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

Metabolized by the liver and erythrocytes to form trichloroethanol, an active metabolite. This reaction is catalyzed by alcohol dehydrogenase and other enzymes. Oxidation of chloral hydrate and trichloroethanol to trichloroacetic acid in the liver and kidneys also occurs to a lesser extent. Trichloroethanol also undergoes glucuronidation to produce an inactive metabolism.


/Chloral hydrate/ biotransformation to trichloroethanol must be rapid, since no parent compound could be detected in even the first samples taken 10 min after administration of 15 mg/kg bw to volunteers.

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. V63 251 (1995)


Chloral hydrate is metabolized by the liver and erythrocytes to form trichloroethanol (an active metabolite). The reduction of chloral hydrate to trichloroethanol (the major metabolite) is catalyzed by alcohol dehydrogenase and other enzymes. ... A small but variable amount of chloral hydrate and a larger portion of trichloroethanol are oxidized to trichloroacetic acid (an inactive metabolite), mainly in the liver and kidneys. Trichloroethanol may also be conjugated with glucuronic acid to form trichloroethanol glucuronide (urochloralic acid), an inactive metabolite. ... The quantities of metabolites excreted in the urine appear to be quite variable not only between different individuals but may even vary in the same individual on different days.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2610


In mammalian species, chloral hydrate is rapidly reduced to trichloroethanol, the metabolite that appears to be responsible for the hypnotic properties of the drug. ... In rodents, a slightly different metabolic pattern is seen, as chloral hydrate is oxidized directly to trichloroacetic acid, and the oxidative pathway from trichloroethanol to trichloroacetate that is observed in humans seems to be absent.

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. V63 251 (1995)


As < 50% of an administered dose of chloral hydrate was recovered as metabolites in urine, yet unknown biotransformation reactions may exist for chloral hydrate in humans.

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. V63 251 (1995)


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


Chloral hydrate is a known human metabolite of Trichloroethylene.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.5 Biological Half-Life

The plasma half-life of trichloroethanol, the active metabolite, is about 7 to 10 hours.

USP. Convention. USPDI - Drug Information for the Health Care Professional. 20th ed. Volume I. Micromedex, Inc. Englewood, CO., 2000. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 859


The average half-life of trichloroethanol glucuronide was 6.7 hr. The average plasma half-life for chloral hydrate metabolites was 8.2 hr; the half-life of the third chloral hydrate metabolite, trichloroacetic acid, was about four days, as it binds extensively to plasma proteins.

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. V63 251 (1995)


The plasma half-life for therapeutic doses of chloral hydrate is 4 to 5 min, whereas for trichloroethanol /a metabolite/ is 8 to 12 hr and for trichloroacetic acid /a metabolite/, 67 hr.

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 586


This study was designed to characterize the kinetics of chloral hydrate (CH) metabolism, and the formation and elimination of trichloroacetate (TCA), dichloroacetate (DCA), trichloroethanol (TCOH), and trichloroethanol glucuronide (TCOG) in male B6C3F1 mice. Mice were dosed with 67.8, 678, and 2034 umol/kg of CH through the tail vein. ... After intravenous administration, CH rapidly disappeared from blood with a terminal half-life ranging from 5 to 24 min. ... The terminal half-lives of TCOH and TCOG were similar, ranging from 0.2 to 0.7 hr. ...

PMID:8971140 Abbas R et al; Drug Metab Dispos 24 (12): 1340-6 (1996)


5.6 Mechanism of Action

Chloral hydrate has CNS depressant effects similar to those of paraldehyde and the barbiturates. The mechanism of action of the drug is not completely known. The CNS depressant effect of chloral hydrate is believed to result mainly from its metabolite, trichloroethanol, although some animal studies have indicated that the rapid onset of sedation and hypnosis that chloral hydrate produces may be due to chloral hydrate itself and that the prolonged duration of action may be due to trichloroethanol.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2610


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24-Feb-2023
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Average Price
(USD/KGS)
Number of Transactions

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