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2D Structure
Also known as: 2,4,6-trimethyl-1,3,5-trioxane, 123-63-7, Paracetaldehyde, Acetaldehyde trimer, Paral, Paraldehyd
Molecular Formula
C6H12O3
Molecular Weight
132.16  g/mol
InChI Key
SQYNKIJPMDEDEG-UHFFFAOYSA-N
FDA UNII
S6M3YBG8QA

A hypnotic and sedative with anticonvulsant effects. However, because of the hazards associated with its administration, its tendency to react with plastic, and the risks associated with its deterioration, it has largely been superseded by other agents. It is still occasionally used to control status epilepticus resistant to conventional treatment. (From Martindale, The Extra Pharmacopoeia, 30th ed, p608-9)
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,4,6-trimethyl-1,3,5-trioxane
2.1.2 InChI
InChI=1S/C6H12O3/c1-4-7-5(2)9-6(3)8-4/h4-6H,1-3H3
2.1.3 InChI Key
SQYNKIJPMDEDEG-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1OC(OC(O1)C)C
2.2 Other Identifiers
2.2.1 UNII
S6M3YBG8QA
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 2,4,6-trimethyl-1,3,5-trioxane

2. 123-63-7

3. Paracetaldehyde

4. Acetaldehyde Trimer

5. Paral

6. Paraldehyd

7. Paraacetaldehyde

8. Elaldehyde

9. S-trimethyltrioxymethylene

10. Paraldeide

11. Triacetaldehyde

12. 2,4,6-trimethyl-s-trioxane

13. 1,3,5-trioxane, 2,4,6-trimethyl-

14. 1,3,5-trimethyl-2,4,6-trioxane

15. Acetaldehyde, Trimer

16. P-acetaldehyde

17. Pcho

18. Nsc 9799

19. 2,4,6-trimethyl-1,3,5-trioxacyclohexane

20. Rcra Waste Number U182

21. Paraldehyde Enema (bpc 1973)

22. Paraldehyde Draught (bpc 1973)

23. Trimethyl Trioxane

24. 2,4,6-trimethyl-1,3,5-trioxaan

25. 2,4,6-trimetil-1,3,5-triossano

26. Paraldehyde (usp)

27. Paraldehyde [usp]

28. Cis-2,4,6-trimethyl-1,3,5-trioxane

29. Paral (tn)

30. S-trioxane, 2,4,6-trimethyl-

31. Nsc-9799

32. 2,4,6-trimethyl-1,3,5-trioxan

33. S6m3ybg8qa

34. Fema No. 4010

35. Chebi:27909

36. 1499-02-1

37. Ncgc00159367-02

38. Ncgc00159367-03

39. Ncgc00159367-04

40. Dsstox_cid_3419

41. Dsstox_rid_77020

42. Dsstox_gsid_23419

43. Paraldehyd [german]

44. Paraldehyde [usan]

45. Paraldeide [italian]

46. Triacetaldehyde [french]

47. Cas-123-63-7

48. Hsdb 3375

49. Einecs 204-639-8

50. Unii-s6m3ybg8qa

51. Un1264

52. Rcra Waste No. U182

53. Brn 0080142

54. Paraldehyde Civ

55. Ai3-03115

56. 2,4,6-trimethyl-1,3,5-trioxaan [dutch]

57. Dea No. 2585

58. 2,4,6-trimetil-1,3,5-triossano [italian]

59. Aldehyde (para)

60. Paraldehyd(german)

61. Mfcd00036208

62. S-trimethyltrioxymethane

63. Paraldehyde, >=97%

64. Paraldehyde [un1264] [flammable Liquid]

65. Paraldehyde [mi]

66. Paraldehyde [fhfi]

67. Paraldehyde [hsdb]

68. 2,6-trimethyl-s-trioxane

69. Ec 204-639-8

70. Paraldehyde [vandf]

71. Paraldehyde [mart.]

72. S-trioxane,4,6-trimethyl-

73. Schembl22870

74. Paraldehyde [who-dd]

75. 5-19-09-00112 (beilstein Handbook Reference)

76. Zinc1886

77. Chembl1410743

78. Dtxsid9023419

79. Schembl20072682

80. Nsc9799

81. Paraldehyde Civ [usp-rs]

82. 1,5-trimethyl-2,4,6-trioxane

83. 2,6-trimethyl-1,3,5-trioxaan

84. 2,6-trimethyl-1,3,5-trioxane

85. 2,6-trimetil-1,3,5-triossano

86. Dtxsid301271154

87. Paraldehyde [ep Monograph]

88. Paraldehyde, >=97.0% (gc)

89. Paraldehyde [usp Monograph]

90. Tox21_111607

91. Tox21_111608

92. Tox21_301299

93. 1,5-trioxane, 2,4,6-trimethyl-

94. Bbl011471

95. Stl146583

96. Akos000120195

97. Tox21_111607_1

98. Db09117

99. Un 1264

100. Wln: T6o Co Eotj B1 D1 F1

101. 2,6-trimethyl-1,3,5-trioxacyclohexane

102. Ncgc00257534-01

103. Vs-02956

104. Ft-0650173

105. P0019

106. Paraldehyde [un1264] [flammable Liquid]

107. Paraldehyde, Lonza Quality, >=99.5% (gc)

108. C07834

109. D00705

110. A805128

111. Q424342

112. J-523868

113. F1908-0170

114. (2alpha,4alpha,6alpha)-2,4,6-trimethyl-1,3,5-trioxane

115. Paraldehyde, United States Pharmacopeia (usp) Reference Standard

116. 26893-98-1

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 132.16 g/mol
Molecular Formula C6H12O3
XLogP30.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass132.078644241 g/mol
Monoisotopic Mass132.078644241 g/mol
Topological Polar Surface Area27.7 Ų
Heavy Atom Count9
Formal Charge0
Complexity63.3
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

Anticonvulsants; Sedatives, Nonbarbiturate

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


Paraldehyde has been used chiefly for the treatment of abstinence phenomena and other psychiatric sates characterized by excitement, and for the emergency treatment of convulsive episodes. Its most persisting use has been in the treatment of delirium tremens.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 368


PARALDEHYDE IS EFFECTIVE IN STATUS EPILEPTICUS, BUT SHOULD BE RESERVED FOR PATIENTS WHO DO NOT RESPOND TO PHENOBARBITAL. ... DRUG IS ALSO FREQUENTLY USED IN DELIRIUM TREMENS, & IN PATIENTS UNDERGOING WITHDRAWAL THERAPY FOR ALCOHOLISM.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1019


VET: HYPNOTIC. LIMITED TO INDUCE ... /CNS DEPRESSION/ AS PREANESTHETIC IN SOME ANIMALS & RARELY AS ANESTHETIC ITSELF.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 413


For more Therapeutic Uses (Complete) data for PARALDEHYDE (10 total), please visit the HSDB record page.


4.2 Drug Warning

IN AT LEAST 8 CASES OF POISONING INVOLVING 4 FATALITIES, USE OF DETERIORATED PARALDEHYDE HAS BEEN IMPLICATED.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 131


PREPARATIONS THAT HAVE BROWNISH COLOR OR SHARP PENETRATING ODOR OF ACETIC ACID SHOULD NOT BE USED.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 1452


ALL CONTAINERS OF PARALDEHYDE, INCLUDING THOSE DISPENSED BY THE PHARMACIST, SHOULD CARRY STATEMENT DIRECTING USER TO DISCARD THE UNUSED CONTENTS OF ANY CONTAINER WHICH HAS BEEN OPENED FOR MORE THAN 24 HR.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 1452


IN NO CASE SHOULD PARALDEHYDE BE TAKEN FROM OLD, PARTIALLY EMPTY CONTAINERS, SINCE AN APPRECIABLE PROPORTION OF THE DRUG MAY HAVE BEEN OXIDIZED TO ACETIC ACID & OTHER DECOMPOSITION PRODUCTS. BECAUSE PARALDEHYDE REACTS RAPIDLY WITH CERTAIN PLASTICS, IT SHOULD BE MEASURED WITH GLASS SYRINGES.

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 367


For more Drug Warnings (Complete) data for PARALDEHYDE (12 total), please visit the HSDB record page.


4.3 Drug Indication

Paraldehyde was used historically as a sedative and hypnotic. It has been used in the treatment of seizures as an anticonvulsant.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Paraldehyde blocks neuromuscular transmission.


5.2 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.)


Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)


5.3 ATC Code

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CC - Aldehydes and derivatives

N05CC05 - Paraldehyde


5.4 Absorption, Distribution and Excretion

Absorption

93% of orally administered paraldehyde is absorbed from the gastrointestinal tract.


Route of Elimination

70-80% is metabolized to carbon dioxide and subsequently exhaled. 11-28% is exhaled as the parent compound. 0.1-2.5% is excreted in the urine as the parent compound.


Paraldehyde is rapidly absorbed from ... IM injection sites. Maximum serum concn, which may range from 34 to 150 ug/ml, are reached within 20-60 minutes following oral admin of 10 ml ... or IM admin of 0.25 ml/kg. ... Although tissue distribution ... has not been extensively studied, it is known that the concn ... in CSF is about 25 to 30% lower than that in the blood. Maximum paraldehyde concn are reached in the CSF 30-60 minutes after oral or IM admin ...

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 1452


Oral paraldehyde is rapidly absorbed and widely distributed; the drug readily crosses the placental barrier. With hypnotic doses, 70 to 80% is metabolized in the liver, most of the remainder is exhaled, and a small amount is excreted in urine.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 368


... PARALDEHYDE EQUILIBRATES RAPIDLY BETWEEN MATERNAL & FETAL BLOODS.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 634


FETAL/MATERNAL CONCN RATIO IS 0.94. /FROM TABLE/

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 100


For more Absorption, Distribution and Excretion (Complete) data for PARALDEHYDE (9 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Paraldehyde is believed to undergo depolymerization to acetaldehyde followed by oxidation by aldehyde dehydrogenase. It is thought to ultimately be metabolized to carbon dioxide and water.


It is believed that paraldehyde is depolymerized to acetaldehyde in the liver & then oxidized by aldehyde dehydrogenase to acetic acid, which is ultimately metabolized to carbon dioxide & water.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 368


5.6 Biological Half-Life

The mean half life is 7.5 hours in a range if 3.5-9.5 hours.


The biological half-life of paraldehyde /in humans/ has been reported to be 3.5 to 9.5 hours with an average of about 7.5 hours.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 1452


5.7 Mechanism of Action

Paraldehyde is believed to reduce the release of acetylcholine in response to neuronal depolarization. The exact mechanism of this effect is unknown.


BELIEVED TO DEPRESS MANY LEVELS OF CNS INCLUDING ASCENDING RETICULAR ACTIVATING SYSTEM TO CAUSE IMBALANCE BETWEEN INHIBITORY & FACILITATORY MECHANISMS.

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1975