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Hexobarbital

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ANALYTICAL

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4 Analytical Methods

Synopsis

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Chemistry

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Also known as: Hexobarbitone, Methylhexabital, Methexenyl, 56-29-1, Evipal, Evipan

Molecular Formula

C₁₂H₁₆N₂O₃

Molecular Weight

236.27 g/mol

InChI Key

UYXAWHWODHRRMR-UHFFFAOYSA-N

FDA UNII

AL8Z8K3P6S

A barbiturate that is effective as a hypnotic and sedative.

1 2D Structure

Hexobarbital

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-(cyclohexen-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione

2.1.2 InChI

InChI=1S/C12H16N2O3/c1-12(8-6-4-3-5-7-8)9(15)13-11(17)14(2)10(12)16/h6H,3-5,7H2,1-2H3,(H,13,15,17)

2.1.3 InChI Key

UYXAWHWODHRRMR-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1(C(=O)NC(=O)N(C1=O)C)C2=CCCCC2

2.2 Other Identifiers

2.2.1 UNII

AL8Z8K3P6S

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Evipan

2. Hexenal

3. Hexobarbital, Sodium

4. Hexobarbitone

5. Sodium Hexobarbital

2.3.2 Depositor-Supplied Synonyms

1. Hexobarbitone

2. Methylhexabital

3. Methexenyl

4. 56-29-1

5. Evipal

6. Evipan

7. Barbidorm

8. Cyclopan

9. Enhexymal

10. Noctivane

11. Sombucaps

12. Sombulex

13. Somnalert

14. Citopan

15. Methylhexabarbital

16. Cyclonal

17. Hexabarbital

18. Narcosan

19. Citodon

20. Dorico

21. Hexanastab Oral

22. Hexenal (barbiturate)

23. Esobarbitale

24. Hexobarbitalum

25. 5-(1-cyclohexen-1-yl)-1,5-dimethylbarbituric Acid

26. N-methyl-5-cyclohexenyl-5-methylbarbituric Acid

27. 1,5-dimethyl-5-(1-cyclohexenyl)barbituric Acid

28. Hexobarbital Ciii

29. 5-(cyclohexen-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione

30. Nsc 71929

31. 5-(1-cyclohexen-1-yl)-1,5-dimethyl-2,4,6(1h,3h,5h)-pyrimidinetrione

32. 5-(1-cyclohexenyl-1)-1-methyl-5-methylbarbituric Acid

33. 2,4,6(1h,3h,5h)-pyrimidinetrione, 5-(1-cyclohexen-1-yl)-1,5-dimethyl-

34. Nsc-71929

35. Al8z8k3p6s

36. Barbituric Acid, 5-(1-cyclohexen-1-yl)-1,5-dimethyl-

37. Chebi:5706

38. Enhexymalum

39. Hexobarbitonum

40. 5-(cyclohex-1-en-1-yl)-1,5-dimethylpyrimidine-2,4,6(1h,3h,5h)-trione

41. Ncgc00159430-02

42. Ncgc00159430-03

43. Ncgc00159430-04

44. Hexobarbital (van)

45. Esobarbitale [dcit]

46. Esobarbitale [italian]

47. Dsstox_cid_3122

48. Dsstox_rid_76882

49. Dsstox_gsid_23122

50. Hexobarbitalum [inn-latin]

51. 5-cyclohex-1-enyl-1,5-dimethyl-pyrimidine-2,4,6-trione

52. 5-(.delta.-1,2-cyclohexenyl)-5-methyl-n-methyl-barbitursaeure

53. 5-cyclohexenyl-1,5-dimethylpyrimidine-2,4,6(1h,3h,5h)-trione

54. 5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione

55. Cas-56-29-1

56. Einecs 200-264-9

57. Hexobarbital (jan/inn)

58. Unii-al8z8k3p6s

59. Ai3-61892

60. Hexobarbital [usp:inn:ban:jan]

61. 5-(delta-1,2-cyclohexenyl)-5-methyl-n-methyl-barbitursaeure [german]

62. (+/-)-hexobarbital

63. 5-(delta-1,2-cyclohexenyl)-5-methyl-n-methyl-barbitursaeure

64. Hexobarbital [mi]

65. Hexobarbital [inn]

66. Hexobarbital [jan]

67. Barbituric Acid,5-dimethyl-

68. Chembl7728

69. Hexobarbital [vandf]

70. Oprea1_350917

71. Schembl29821

72. Hexobarbital [mart.]

73. Mls001143909

74. Hexobarbital [who-dd]

75. Dtxsid9023122

76. Hexobarbital [ep Impurity]

77. Hms2272k03

78. Nsc71929

79. Hexobarbital 1.0 Mg/ml In Methanol

80. Tox21_111661

81. Tox21_111662

82. Stk696034

83. 5-cyclohex-1-en-1-yl-1,5-dimethylpyrimidine-2,4,6(1h,3h,5h)-trione

84. 5-cyclohex-1-en-1-yl-2-hydroxy-1,5-dimethylpyrimidine-4,6(1h,5h)-dione

85. Akos000355976

86. Akos016347605

87. Tox21_111661_1

88. Db01355

89. Ac-16076

90. Smr000473348

91. Db-052887

92. Wln: T6vmvnv Fhj D1 F1 F- Al6utj

93. D01071

94. 5-(cyclohexen-1-yl)-1,5-dimethylbarbitursaeure

95. 5-(cyclohexen-1-yl)-1,5-dimethylbarbituric Acid

96. Q421183

97. 5-(cyclohex-1-enyl)-1,5-dimethyl-barbituric Acid

98. Hexobarbital, United States Pharmacopeia (usp) Reference Standard

99. 2,6(1h,3h,5h)-pyrimidinetrione, 5-(1-cyclohexen-1-yl)-1,5-dimethyl-

100. 5-(1-cyclohexenyl)-1,5-dimethyl-2,4,6(1h,3h,5h)-pyrimidinetrione

101. Hexobarbital Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₆N₂O₃
Molecular Weight	236.27 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	236.11609238 g/mol
Monoisotopic Mass	236.11609238 g/mol
Topological Polar Surface Area	66.5 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	428
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the induction of anesthesia prior to the use of other general anesthetic agents and for induction of anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Hexobarbital is a barbiturate derivative having hypnotic and sedative effects. It was subsequently used in the 1940s and 1950s as an anesthetic for surgery. Furthermore, the agent also demonstrates a fairly quick onset of action that also possesses a short duration of action. However it can be difficult to control the depth of anesthesia with hexobarbital which makes it quite dangerous, and it has now been replaced by safer drugs in human medicine, usually thiopental would be the barbiturate of choice for this application these days.

5.2 MeSH Pharmacological Classification

GABA Modulators

Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here. (See all compounds classified as GABA Modulators.)

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.)

5.3 ATC Code

N - Nervous system

N01 - Anesthetics

N01A - Anesthetics, general

N01AF - Barbiturates, plain

N01AF02 - Hexobarbital

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CA - Barbiturates, plain

N05CA16 - Hexobarbital

5.4 Metabolism/Metabolites

Hepatic.

5.5 Mechanism of Action

Hexobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABA-A receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.

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