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Chemistry

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Also known as: Trichloromethane, 67-66-3, Methane, trichloro-, Trichlormethan, Formyl trichloride, Trichloroform
Molecular Formula
CHCl3
Molecular Weight
119.37  g/mol
InChI Key
HEDRZPFGACZZDS-UHFFFAOYSA-N
FDA UNII
7V31YC746X

Chloroform
A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.
1 2D Structure

Chloroform

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
chloroform
2.1.2 InChI
InChI=1S/CHCl3/c2-1(3)4/h1H
2.1.3 InChI Key
HEDRZPFGACZZDS-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(Cl)(Cl)Cl
2.2 Other Identifiers
2.2.1 UNII
7V31YC746X
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Trichloromethane

2.3.2 Depositor-Supplied Synonyms

1. Trichloromethane

2. 67-66-3

3. Methane, Trichloro-

4. Trichlormethan

5. Formyl Trichloride

6. Trichloroform

7. Methenyl Trichloride

8. Methyl Trichloride

9. Methane Trichloride

10. Chloroforme

11. Chcl3

12. R 20 (refrigerant)

13. Cloroformio

14. Triclorometano

15. Trichloormethaan

16. Freon 20

17. 1,1,1-trichloromethane

18. Rcra Waste Number U044

19. Methenyl Chloride

20. Nci-c02686

21. Methylidyne Trichloride

22. Refrigerant R20

23. Hsdb 56

24. Chloroformum

25. Chloroform Bp

26. Trichloro-methane

27. Nsc 77361

28. R 20

29. Chloroform [un1888] [poison]

30. Hcc 20

31. Nsc-77361

32. Chebi:35255

33. 7v31yc746x

34. Ncgc00090794-01

35. Chloroform Chcl3

36. Chloroform, Hplc Grade

37. Dsstox_cid_306

38. Dsstox_rid_75501

39. Dsstox_gsid_20306

40. Chloroform, Analytical Standard

41. Chloroforme [french]

42. Caswell No. 192

43. Cloroformio [italian]

44. Trichlormethan [czech]

45. Chloroform [nf Xvii]

46. Trichloormethaan [dutch]

47. Triclorometano [italian]

48. Mfcd00000826

49. Cas-67-66-3

50. Chloroform [nf]

51. Ccris 137

52. Chloroform, Acs

53. Chloroformwith Amylene

54. Chloroformwith Ethanol

55. Einecs 200-663-8

56. Un1888

57. Rcra Waste No. U044

58. Epa Pesticide Chemical Code 020701

59. Brn 1731042

60. Chlorform

61. Chloroforrn

62. Cloroform

63. Trichlormethane

64. Trichlorocarbon

65. Chloro Form

66. Chloro-form

67. Unii-7v31yc746x

68. Chloroform-

69. Ai3-24207

70. Chloroform, For Hplc, >=99.8%, Contains 0.5-1.0% Ethanol As Stabilizer

71. Trichloro- Methane

72. Chloroform Solution

73. Methane Trichloride

74. Tris(chloranyl)methane

75. Ccl3h

76. Hccl3

77. Chloroform, For Hplc

78. Trichloromethane, 9ci

79. Chloroform [ii]

80. Chloroform [mi]

81. Chloroform, Ethanol-free

82. Chloroformium Pro Narcosi

83. Wln: Gygg

84. Chloroform [hsdb]

85. Chloroform [iarc]

86. Chloroform [inci]

87. Aqualine™ Matrix K

88. Chloroform [vandf]

89. Chloroformum [hpus]

90. Ec 200-663-8

91. Chloroform [mart.]

92. Chloroform [usp-rs]

93. Chloroform [who-dd]

94. 4-01-00-00042 (beilstein Handbook Reference)

95. Chembl44618

96. Chloroform, Environmental Grade

97. Chloroform, P.a., 99.8%

98. Gtpl2503

99. Chloroform [green Book]

100. Chloroform - Reagent Grade Acs

101. Dtxsid1020306

102. R 20 (van)

103. Chloroform With Amylene Hplc Grade

104. Chloroform, Spectrophotometric Grade

105. Nsc77361

106. Zinc8214524

107. Chloroform (stabilized With Ethanol)

108. Tox21_111024

109. Tox21_202494

110. Chloroform, For Hplc, >=99.5%

111. Chloroform, For Hplc, >=99.8%

112. Akos000269026

113. Chloroform 100 Microg/ml In Methanol

114. Db11387

115. Un 1888

116. Chloroform 5000 Microg/ml In Methanol

117. Chloroform, Purification Grade, >=99%

118. Ncgc00090794-02

119. Ncgc00260043-01

120. F 20

121. Trichloromethane 10 Microg/ml In Methanol

122. Chloroform, Jis Special Grade, >=99.0%

123. Trichloromethane 100 Microg/ml In Methanol

124. C0819

125. Ft-0623661

126. Trichloromethane 5000 Microg/ml In Methanol

127. Chlorobutanol Impurity A [ep Impurity]

128. Chloroform, Hplc Grade Stabilized With Ethanol

129. Chloroform (stabilized With 2-methyl-2-butene)

130. Chloroform, Saj Super Special Grade, >=99.0%

131. A835850

132. L023971

133. Q172275

134. Brd-k88785477-001-01-8

135. Chloroform, For Hplc, >=99.8%, Amylene Stabilized

136. Chloroform, 99.8%, Acs Reagent Stabilized With Ethanol

137. Chloroform, Technical, Amylene Stabilized, >=99% (gc)

138. F0001-1775

139. Chloroform, Technical Grade, 95%, Contains 50 Ppm Amylene

140. Chloroform, Anhydrous, Contains Amylenes As Stabilizer, >=99%

141. Chloroform, For Hplc, >=99.8% (chloroform + Ethanol, Gc)

142. Chloroform, For Residue Analysis, Suitable For 5000 Per Jis

143. Chloroform Solution, 200 Mug/ml In Methanol, Analytical Standard

144. Chloroform Stabilized With 50-200 Ppm Amylene Acs Reagent Grade

145. Chloroform, >=99%, Pcr Reagent, Contains Amylenes As Stabilizer

146. Chloroform, Acs Reagent, >=99.8%, Contains Amylenes As Stabilizer

147. Chloroform, Ar, Contains 1-2% Ethanol As Stabilizer, >=99.5%

148. Chloroform, Ar, Contains 100 Ppm Amylene As Stabilizer, >=99.5%

149. Chloroform, Contains 100-200 Ppm Amylenes As Stabilizer, >=99.5%

150. Chloroform, Contains Amylenes As Stabilizer, Acs Reagent, >=99.8%

151. Chloroform, Contains Ethanol As Stabilizer, Acs Reagent, >=99.8%

152. Chloroform, Lr, Contains 100 Ppm Amylene As Stabilizer, >=99%

153. Chloroform, P.a., Acs Reagent, 99.8%, Contains 0.005% Amylene

154. Chloroform, Saj First Grade, >=99.0%, Contains 0.4-0.8% Ethanol

155. Chloroform, Uv Hplc Spectroscopic, 99.9%, Contains 50 Ppm Amylene

156. Chloroform Solution, Certified Reference Material, 5000 Mug/ml In Methanol

157. Chloroform, Acs Reagent, Reag. Ph. Eur., Contains Ethanol As Stabilizer

158. Chloroform, Anhydrous, >=99%, Contains 0.5-1.0% Ethanol As Stabilizer

159. Chloroform, Pharmaceutical Secondary Standard; Certified Reference Material

160. Chloroform, Puriss. P.a., Reag. Iso, Reag. Ph. Eur., 99.0-99.4% (gc)

161. Chloroform, Suitable For 300 Per Jis, >=99.0%, For Residue Analysis

162. Chloroform, Uv Hplc Spectroscopic, 99.0%, Contains 0.6-1.0% Ethanol

163. Chloroform Solution, Nist Standard Reference Material, 1% In Acetone-d6 (99.9 Atom % D)

164. Chloroform Solution, Nmr Reference Standard, 1% In Acetone-d6 (99.9 Atom % D)

165. Chloroform Solution, Nmr Reference Standard, 3% In Acetone-d6 (99.9 Atom % D)

166. Chloroform, Acs Reagent, >=99.8%, Contains 0.5-1.0% Ethanol As Stabilizer

167. Chloroform, Acs Spectrophotometric Grade, >=99.8%, Contains Amylenes As Stabilizer

168. Chloroform, Biotech. Grade, >=99.8%, Contains 0.5-1.0% Ethanol As Stabilizer

169. Chloroform, P.a., Acs Reagent, Reag. Iso, 99.8%, Contains 50 Ppm Amylene

170. Chloroform, Puriss. P.a., Acs Reagent, >=99.8% (chloroform + Ethanol, Gc)

171. Chloroform, Reagentplus(r), >=99.8%, Contains 0.5-1.0% Ethanol As Stabilizer

172. Residual Solvent Class 2 - Chloroform, United States Pharmacopeia (usp) Reference Standard

173. 8013-54-5

174. Chloroform Solution, Nmr Reference Standard, 0.3% In Acetone-d6 (99.9 Atom % D), Nmr Tube Size 3 Mm X 8 In.

175. Chloroform Solution, Nmr Reference Standard, 0.3% In Acetone-d6 (99.9 Atom % D), Nmr Tube Size 5 Mm X 8 In.

176. Chloroform Solution, Nmr Reference Standard, 1% In Acetone-d6 (99,9 Atom % D), Tms 0.1 %, Nmr Tube Size 5 Mm X 8 In.

177. Chloroform Solution, Nmr Reference Standard, 1% In Acetone-d6 (99.9 Atom % D), Nmr Tube Size 10 Mm X 8 In.

178. Chloroform Solution, Nmr Reference Standard, 1% In Acetone-d6 (99.9 Atom % D), Nmr Tube Size 3 Mm X 8 In.

179. Chloroform Solution, Nmr Reference Standard, 1% In Acetone-d6 (99.9 Atom % D), Nmr Tube Size 4 Mm X 8 In.

180. Chloroform Solution, Nmr Reference Standard, 1% In Acetone-d6 (99.9 Atom % D), Nmr Tube Size 8 Mm X 8 In.

181. Chloroform Solution, Nmr Reference Standard, 10% In Acetone-d6 (99.9 Atom % D), Nmr Tube Size 3 Mm X 8 In.

182. Chloroform Solution, Nmr Reference Standard, 2% In Acetone-d6 (99.9 Atom % D), Nmr Tube Size 5 Mm X 8 In.

183. Chloroform Solution, Nmr Reference Standard, 2% In Chloroform-d (99.8 Atom % D), Nmr Tube Size 3 Mm X 8 In.

184. Chloroform Solution, Nmr Reference Standard, 2% In Chloroform-d (99.8 Atom % D), Nmr Tube Size 5 Mm X 8 In.

185. Chloroform Solution, Nmr Reference Standard, 20% In Acetone-d6 (99.9 Atom % D), Nmr Tube Size 5 Mm X 8 In.

186. Chloroform Solution, Nmr Reference Standard, 3% In Acetone-d6 (99.9 Atom % D), Tms 0.2 %, Nmr Tube Size 3 Mm X 8 In.

187. Chloroform Solution, Nmr Reference Standard, 3% In Acetone-d6 (99.9 Atom % D), Tms 0.2 %, Nmr Tube Size 5 Mm X 8 In.

188. Chloroform Solution, Nmr Reference Standard, 5% In Acetone-d6 (99.9 Atom % D), Chromium(iii) Acetylacetonate 0.2 %

189. Chloroform Solution, Nmr Reference Standard, 5% In Acetone-d6 (99.9 Atom % D), Chromium(iii) Acetylacetonate 2 %, Nmr Tube Size 10 Mm X 8 In.

190. Chloroform Solution, Nmr Reference Standard, 5% In Acetone-d6 (99.9 Atom % D), Nmr Tube Size 3 Mm X 8 In.

191. Chloroform Solution, Nmr Reference Standard, 5% In Acetone-d6 (99.9 Atom % D), Nmr Tube Size 5 Mm X 8 In.

192. Chloroform Solution, Nmr Reference Standard, 50% In Acetone-d6 (99.9 Atom % D), Chromium(iii) Acetylacetonate 0.2 %

193. Chloroform Solution, Nmr Reference Standard, 50% In Acetone-d6 (99.9 Atom % D), Chromium(iii) Acetylacetonate 0.2 %, Nmr Tube Size 10 Mm X 8 In.

194. Chloroform, Acs Spectrophotometric Grade, >=99.8%, Contains 0.5-1.0% Ethanol As Stabilizer

195. Chloroform, Contains Ethanol As Stabilizer, Meets Analytical Specification Of Dab9, Bp, 99-99.4% (gc)

196. Chloroform, Hplc Plus, For Hplc, Gc, And Residue Analysis, >=99.9%, Contains 0.5-1.0% Ethanol As Stabilizer

197. Chloroform, Hplc Plus, For Hplc, Gc, And Residue Analysis, >=99.9%, Contains Amylenes As Stabilizer

198. Residual Solvent - Chloroform, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 119.37 g/mol
Molecular Formula CHCl3
XLogP32.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Exact Mass117.914383 g/mol
Monoisotopic Mass117.914383 g/mol
Topological Polar Surface Area0 Ų
Heavy Atom Count4
Formal Charge0
Complexity8
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

MEDICATION (VET): As inhalation anesthetic in horses & now rarely in cattle, sheep, cats or dogs because of dangerous complications & superior alternatives; internally, well dilute in intestinal colic & flatulence; in expectorants, & less commonly as anthelmintic (swine, dogs) ... . /Former use/

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 104


MEDICATION (VET): Used/ externally, as liniment-type counterirritant for relief of deep seated pain, to expel screwworm larvae from wounds, as skin cleanser (fat solvent), & as skin coolant & local anesthetic due to its evaporation. ... Internally, it is given in various mixt well dilute to avoid gastric irritation ... . /Former use/

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 104


Has been used as an anesthetic and in pharmaceutical preparations.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 379


Chloroform was used chiefly as an anesthetic and in pharmaceutical preparation immediately prior to World War II. However, these uses have been banned.

Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. 5(79) 694


4.2 Drug Warning

An increased incidence of cardiac arrhythmias has been demonstrated during surgery in patients anesthetized with chloroform as compared with other anesthetic agents at vapor concentrations of 22,500 ppm.

Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 2


Maternal Medication usually Compatible with Breast-Feeding: Chloroform: Reported Sign or Symptom in Infant or Effect on Lactation: None. /from Table 6/

Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 140 (1994)


4.3 Minimum/Potential Fatal Human Dose

Fatal doses of liquid anesthetic agents by ingestion or inhalation are approx as follows: ... chloroform, 10 mL ... .

Dreisbach, R.H. Handbook of Poisoning. 12th ed. Norwalk, CT: Appleton and Lange, 1987., p. 314


The mean lethal dose for an adult is estimated to be about 45 g.

WHO; EHC163: Chloroform (1994) Available from, as of January 2, 2018: https://www.inchem.org/documents/ehc/ehc/ehc163.htm


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.)


5.2 ATC Code

N - Nervous system

N01 - Anesthetics

N01A - Anesthetics, general

N01AB - Halogenated hydrocarbons

N01AB02 - Chloroform


5.3 Absorption, Distribution and Excretion

Chloroform can be absorbed through lung, from GI tract and to some extent through skin. Inhalation route is ... primary source of ... absorption in man.

Doull, J., C.D. Klaassen, and M. D. Amdur (eds.). Casarett and Doull's Toxicology. 2nd ed. New York: Macmillan Publishing Co., 1980., p. 47


Chloroform is rapidly absorbed & distributed to all organs, with relatively high concn in nervous tissue. After intraduodenal injection of (14)C-chloroform to rats, 70% ... was found unchanged in expired air & 4% as (14)CO2(carbon dioxide) during 24 hr. ... Liver and, to much lesser extent, kidney were main organs in which CO2 was formed.

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. V20 414 (1979)


In man, pulmonary excretions of chloroform and its CO2 (carbon dioxide) metab account substantially for single oral dose of 0.5 or 1.0 g. Amongst 9 subjects, up to 68% of dose is excreted unchanged & up to 51% of CO2; not more than 4% of dose is excreted unchanged after 8 hr.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 329


... /Chloroform crosses/ placenta rapidly and enters fetal circulation.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 635


For more Absorption, Distribution and Excretion (Complete) data for Chloroform (50 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

When (14)C-chloroform was admin orally to mice, rats, & monkeys, radioactivity was found in expired air. Most of dose was excreted unchanged by monkeys, as (14)CO2 (carbon dioxide) by mice, & as both by rats. Three metabolites were detected in urine of rats & mice, one of which was identified as urea.

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. V20 414 (1979)


Haloforms are metabolized to carbon monoxide by hepatic microsomal mixed function oxidases & this reaction is markedly stimulated by sulfhydryl cmpd. Max stimulation occurred at 0.5 mmol glutathione. A mechanism for conversion to carbon monoxide is proposed.

PMID:526325 Stevens JL et al; Biochemical Pharmacology 28: 3189 (1979)


Trihalomethanes (haloforms) were metab to carbon monoxide by rat liver microsomal fraction requiring nadph & molecular oxygen. Metabolism followed halide order; thus, chloroform yielded smallest amt. Results suggest cytochrome p450 dependent system.

Ahmed AE et al; Drug Metabolism Disposition 5 (2): 198 (1976)


Deuterium-labeled chloroform was less toxic and less readily metabolized than /normal/ chloroform, suggesting that the cleavage of the C-H bond is the rate-limiting step in the process resulting in hepatotoxicity.

Pohl LR; Rev Biochem Toxicol 1: 79 (1979)


For more Metabolism/Metabolites (Complete) data for Chloroform (22 total), please visit the HSDB record page.


5.5 Biological Half-Life

Whole body: 1.5 hours; [TDR, p. 318]

TDR - Ryan RP, Terry CE, Leffingwell SS (eds). Toxicology Desk Reference: The Toxic Exposure and Medical Monitoring Index, 5th Ed. Washington DC: Taylor & Francis, 1999., p. 318


After inhalation of approximately 5 mg (38)Cl-chloroform, about 80% of the chloroform was found to have been absorbed ... . Eight volunteers expired 18 to 67% of an oral dose of 500 mg (13)C-chloroform (in capsules of olive oil) unchanged; in two subjects, about half of the dose was eliminated in the expired air as (13)CO2. The decline in the concentration of chloroform in blood was described by a two-compartment model, with initial and second-phase half-lives of 14 and 90 min, respectively, averaged over four subjects.

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. V73 153 (1999)


In humans given a single oral dose of 0.5 g chloroform, about 50-52% of the dose was absorbed, and virtually all of the absorbed dose was metabolized to carbon dioxide. Blood levels peaked after 1.5 hr and declined in line with a two-compartment model with half-lives of 13 and 90 min, respectively ...

WHO; Concise International Chemical Assessment Document 58-chloroform. 2004 Available from, as of August 26, 2008: https://www.inchem.org/documents/cicads/cicads/cicad58.htm


5.6 Mechanism of Action

The feasibility of an oxygen-independent mechanism of chloroform bioactivation was indicated by the covalent binding to lipid and protein occurring in anaerobic incubations of chloroform and microsomes in the presence of NADPH. Under these conditions, the loss of cytochrome p450 and the inhibition of related mono-oxygenases were also observed. The chloroform anoxic biotransformation was negligible in uninduced microsomes and seemed to be catalyzed mainly by phenobarbital-inducible p450 isozymes. Biotransformation could also be supported by NADH as the source of reducing equivalents. Anaerobic metabolism of chloroform led to decreased levels of the main phenobarbital-induced p450 isozymes even at low chloroform concentration, and did not affect benzo(a)pyrene hydroxylase activity. These effects were not decreased by thiolic compounds. The oxidation products of chloroform caused a general impairment of the monoxygenase system, probably related to the formation of protein aggregates with very high molecular weight. In the presence of physiological concentrations of GSH, the targets of aerobically-produced metabolite were lipids, and, to a smaller extent, p450. At low chloroform concentrations and/or in the presence of GSH, the most changes to microsomal structures seemed to be produced by the reductively-formed intermediates.

PMID:3769050 Testai E, Vittozi L; Chem-Biol Interact 59 (2): 157-72 (1986)


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05-Jan-2021
30-Sep-2024
KGS
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