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Also known as: 57-15-8, Chlorbutol, Chloretone, 1,1,1-trichloro-2-methyl-2-propanol, 1,1,1-trichloro-2-methylpropan-2-ol, Chloreton
Molecular Formula
C4H7Cl3O
Molecular Weight
177.45  g/mol
InChI Key
OSASVXMJTNOKOY-UHFFFAOYSA-N
FDA UNII
HM4YQM8WRC

Chlorobutanol Hemihydrate
A colorless to white crystalline compound with a camphoraceous odor and taste. It is a widely used preservative in various pharmaceutical solutions, especially injectables. Also, it is an active ingredient in certain oral sedatives and topical anesthetics.
1 2D Structure

Chlorobutanol Hemihydrate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1,1,1-trichloro-2-methylpropan-2-ol
2.1.2 InChI
InChI=1S/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3
2.1.3 InChI Key
OSASVXMJTNOKOY-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C)(C(Cl)(Cl)Cl)O
2.2 Other Identifiers
2.2.1 UNII
HM4YQM8WRC
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acetonchloroform

2. Anhydrous Chlorobutanol

3. Chlorbutol

4. Chloretone

5. Chlorobutanol, Anhydrous

6. Trichlorbutanol

2.3.2 Depositor-Supplied Synonyms

1. 57-15-8

2. Chlorbutol

3. Chloretone

4. 1,1,1-trichloro-2-methyl-2-propanol

5. 1,1,1-trichloro-2-methylpropan-2-ol

6. Chloreton

7. Chlorbutanol

8. Acetonchloroform

9. Acetone Chloroform

10. Acetochlorone

11. Chlortran

12. Anhydrous Chlorobutanol

13. Coliquifilm

14. Clortran

15. Dentalone

16. Khloreton

17. Methaform

18. Sedaform

19. Chlorobutanol, Anhydrous

20. 2-propanol, 1,1,1-trichloro-2-methyl-

21. Trichlorisobutylalcohol

22. Trichloro-tert-butanol

23. Chlorobutanolum

24. Trichlorobutanol

25. Trichloro-t-butyl Alcohol

26. 2-(trichloromethyl)-2-propanol

27. 1,1,1-trichloro-tert-butyl Alcohol

28. Tert-trichlorobutyl Alcohol

29. Beta,beta,beta-trichloro-tert-butyl Alcohol

30. Trichloro-tert-butyl Alcohol

31. Nsc 44794

32. Chlorobutanol Hemihydrate

33. 2-(trichloromethyl)propan-2-ol

34. 2-propanol, 2-methyl-1,1,1-trichloro-

35. Hm4yqm8wrc

36. Nsc-44794

37. 1,1,1-trichloro-2-methyl-propan-2-ol

38. Mfcd00004461

39. 6001-64-5

40. Ncgc00159392-02

41. Ncgc00159392-05

42. Chlorbutanolum

43. Chlorbutolum

44. Chlorobutanol Hydrate

45. Dsstox_cid_21217

46. Dsstox_rid_79651

47. Wln: Qx1&1&xggg

48. Dsstox_gsid_41217

49. .beta.,.beta.,.beta.-trichloro-tert-butyl Alcohol

50. Caswell No. 185

51. Clorobutanolo [dcit]

52. 1,1-trichloro-tert-butyl Alcohol

53. Clorobutanol

54. Clorobutanolo

55. 1,1-trichloro-2-methyl-2-propanol

56. 2-propanol,1,1-trichloro-2-methyl-

57. Cas-57-15-8

58. Clorobutanol [inn-spanish]

59. Chlorobutanolum [inn-latin]

60. .beta.,.beta.-trichloro-tert-butyl Alcohol

61. Trichloro-2-methylpropan-2-ol

62. 28471-22-9

63. Hsdb 2761

64. Nsc-760101

65. Unii-hm4yqm8wrc

66. Einecs 200-317-6

67. Epa Pesticide Chemical Code 017501

68. Brn 0878167

69. 1, 1, 1-trichloro-2-methyl-2-propanol Hydrate

70. Acetonechloroform

71. Ai3-00048

72. 2-propanol, Trichloro-2-methyl-

73. Chloretone (tn)

74. Chlorobutanol [inn:ban:jan:nf]

75. Chloretone Hemihydrate

76. 2,2,2-trichloro-1,1-dimethylethanol

77. Chlorobutanol, Hydrous

78. T-trichlorobutyl Alcohol

79. Chlorobutanol [ii]

80. Chlorobutanol [mi]

81. Chlorobutanol [inn]

82. Chlorobutanol [jan]

83. Schembl1040

84. Chlorobutanol [hsdb]

85. Chlorobutanol [inci]

86. Acetone Chloroform Hemihydrate

87. Chlorobutanol [vandf]

88. 4-01-00-01629 (beilstein Handbook Reference)

89. 2-trichhloromethyl-2-propanol

90. Chlorobutanol [usp-rs]

91. Chlorobutanol [who-dd]

92. Chlorobutanol [who-ip]

93. Chembl1439973

94. Chlorobutanol (jp17/nf/inn)

95. Dtxsid1041217

96. 2-(trichloromethyl)-propan-2-ol

97. Nsc4596

98. Nsc5208

99. Chebi:134813

100. Molport-003-925-931

101. Chlorobutanol [green Book]

102. Hms3264c17

103. Pharmakon1600-01506102

104. Cs-b1703

105. Hy-b1263

106. Nsc-4596

107. Nsc-5208

108. Nsc44794

109. Zinc1482005

110. Chlorobutanol [ep Monograph]

111. Tox21_111629

112. Bdbm50417941

113. Nsc760101

114. S3705

115. Chlorobutanol, Anhydrous [ii]

116. Akos003619059

117. Chlorobutanolum [who-ip Latin]

118. Tox21_111629_1

119. 2-methyl-1,1,1-trichloro-2-propanol

120. Ccg-213842

121. Db11386

122. Ncgc00159392-03

123. Ncgc00159392-04

124. Chlorobutanol, Anhydrous [who-ip]

125. Cs-15316

126. Sy277495

127. Ft-0605936

128. Ft-0612881

129. T0386

130. Chlorobutanol, Anhydrous [ep Impurity]

131. En300-19331

132. C13278

133. D01942

134. Ab01563200_01

135. 1,1,1-trichloro-2-methylpropan-2-ol Hemihydrate

136. Sr-01000944257

137. Q1047468

138. Sr-01000944257-1

139. W-105484

140. Z1259084902

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 177.45 g/mol
Molecular Formula C4H7Cl3O
XLogP32
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass175.956248 g/mol
Monoisotopic Mass175.956248 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count8
Formal Charge0
Complexity83.8
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

Adrenergic alpha-Agonists; Adrenergic Agents; Sympathomimetics; Vasoconstrictor Agents

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


TOPICALLY AS SOLN IN CLOVE OIL AS DENTAL ANALGESIC. IT HAS LOCAL ANESTHETIC POTENCY TO MILD DEGREE & HAS BEEN EMPLOYED AS ANESTHETIC DUSTING POWDER (1 TO 5%) OR OINTMENT (10%).

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1222


WHEN ADMIN ORALLY, IT HAS MUCH THE SAME THERAPEUTIC USE AS CHLORAL HYDRATE. HENCE, CHLOROBUTANOL HAS BEEN EMPLOYED AS SEDATIVE & HYPNOTIC. IT HAS BEEN TAKEN ORALLY TO ALLAY VOMITING DUE TO GASTRITIS. DOSE--TOPICAL. ... IN TABLETS OR CAPSULES.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1222


MEDICATION (VET): ANTISEPTIC & LOCAL ANESTHETIC; INTERNALLY, IT IS USED AS SEDATIVE & HYPNOTIC. IT APPEARS TO BE OF VALUE IN GASTRITIS WITH PERSISTENT VOMITING IN DOGS.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1222


For more Therapeutic Uses (Complete) data for CHLORETONE (7 total), please visit the HSDB record page.


4.2 Drug Warning

VET WARNING: ... NOT FOR USE AS MOTION SICKNESS DRUG IN CATS AS REPEATED USE IN THIS SPECIES CAUSES RESP CENTER DEPRESSION & MAY BE FATAL. AVOID USE IN ANIMALS WITH LIVER OR KIDNEY PATHOLOGY.

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


RESEMBLES CHLORAL HYDRATE BUT NO GASTRIC IRRITATION.

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-177


ALLERGIC REACTIONS ... INCLUDE ERYTHEMA, SCARLATINIFORM EXANTHEMS, URTICARIA, AND ECZEMATOID DERMATITIS. THE ERUPTION USUALLY BEGINS ON THE FACE OR BACK AND SPREADS TO THE NECK, CHEST, AND ARMS; IT MAY BE FOLLOWED BY DESQUAMATION ... /CHLORAL HYDRATE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 128


UNDESIRABLE CNS EFFECTS INCLUDE LIGHTHEADEDNESS, MALAISE, ATAXIA, & NIGHTMARES. "HANGOVER" ALSO MAY OCCUR ... /CHLORAL HYDRATE/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 381


4.3 Minimum/Potential Fatal Human Dose

4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB).

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-177


4.4 Drug Indication

No approved therapeutic indications on its own.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Chlorobutanol is a detergent preservative with a broad spectrum of antimicrobial activity. _In vitro_, chlorobutanol demonstrated to inhibit platelet aggregation and release via unknown mechanisms. A study proposes that the antiplatelet effect of chlorobutanol may occur from inhibition of the arachidonic acid pathway. It attenuated thromboxane B2 formation, elevation of cytosolic free calcium, and ATP release, and additionally exhibited a significant inhibitory activity toward several aggregation inducers in a time- and concentration-dependent manner. Chlorobutanol may exert a direct negative inotropic effect on myocardial cells to isometric tension produced by the heart. Chlorobutanol was shown to induce conjunctival and corneal cell toxicity _in vitro_: at a concentration of 0.1%, Cbl caused near depletion of the squamous layer while degeneration of corneal epithelial cells, generation of conspicuous membranous blebs, cytoplasmic swelling, and occasional breaks in the external cell membrane were observed at a concentration of 0.5%.


5.2 MeSH Pharmacological Classification

Preservatives, Pharmaceutical

Substances added to pharmaceutical preparations to protect them from chemical change or microbial action. They include ANTI-BACTERIAL AGENTS and antioxidants. (See all compounds classified as Preservatives, Pharmaceutical.)


5.3 ATC Code

A - Alimentary tract and metabolism

A04 - Antiemetics and antinauseants

A04A - Antiemetics and antinauseants

A04AD - Other antiemetics

A04AD04 - Chlorobutanol


5.4 Absorption, Distribution and Excretion

Absorption

Following oral administration in healthy subjects, the plasma concentration fell by 50% in 24 hours post-administration.


Route of Elimination

Under physiological conditions, chlorobutanol is unstable. The mean urinary recovery accounts for 9.6% of the dose orally administered.


Volume of Distribution

The volume of distribution was approximately 233 141 L in healthy individuals receiving oral chlorobutanol.


Clearance

In healthy subjects, the clearance was approximately 11.6 1.0 mL/min following oral administration.


5.5 Metabolism/Metabolites

Chlorobutanol is reported to undergo glucuronidation and sulphation.


5.6 Biological Half-Life

Following oral administration, the terminal elimination half life in healthy subjects was 10.3 1.3 days.


5.7 Mechanism of Action

As a detergent, chlorobutanol disrupts the lipid structure of the cell membrane and increases the cell permeability, leading to cell lysis. It induces conjunctival and corneal cell toxicity via causing cell retraction and cessation of normal cytokines, cell movement, and mitotic activity. It disrupts the barrier and transport properties of the corneal epithelium as well as inhibits the utilization of oxygen by the cornea. Chlorobutanol also inhibits oxygen use by the cornea, which increases susceptibility to infection.


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12-Jan-2021
28-Oct-2024
KGS
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