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Chemistry

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Also known as: Sodium thiopental, Sodium pentothal, Thiopentone sodium, Farmotal, Hypnostan, Leopental

Molecular Formula

C₁₁H₁₇N₂NaO₂S

Molecular Weight

264.32 g/mol

InChI Key

AWLILQARPMWUHA-UHFFFAOYSA-M

A barbiturate that is administered intravenously for the induction of general anesthesia or for the production of complete anesthesia of short duration.

1 2D Structure

Thiopental Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;5-ethyl-4,6-dioxo-5-pentan-2-yl-1H-pyrimidine-2-thiolate

2.1.2 InChI

InChI=1S/C11H18N2O2S.Na/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15;/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16);/q;+1/p-1

2.1.3 InChI Key

AWLILQARPMWUHA-UHFFFAOYSA-M

2.1.4 Canonical SMILES

CCCC(C)C1(C(=O)NC(=NC1=O)[S-])CC.[Na+]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Bomathal

2. Nesdonal

3. Penthiobarbital

4. Pentothal

5. Pentothal Sodico

6. Sodipental

7. Thiomebumal

8. Thionembutal

9. Thiopental

10. Thiopental Nycomed

11. Thiopentobarbital

12. Thiopentone

13. Tiobarbital Braun

14. Trapanal

2.2.2 Depositor-Supplied Synonyms

1. Sodium Thiopental

2. Sodium Pentothal

3. Thiopentone Sodium

4. Farmotal

5. Hypnostan

6. Leopental

7. Nesdonal

8. Ravonal

9. Penthiobarbital Sodium

10. Sodium Thiopentone

11. Thiomebumal Sodium

12. Pentothal

13. Trapanal

14. 71-73-8

15. Thiopentalum Natricum

16. Tiopental Sodico

17. Sodium Pentothiobarbital

18. Sodium Thiopentobarbital

19. Thiopental Sodique

20. Monosodium 5-ethyl-5-(1-methylbutyl) Thiobarbiturate

21. Sodium 5-ethyl-5-(1-methylbutyl)-2-thiobarbiturate

22. Pentothal Sodium-potassium Salt

23. Chebi:9561

24. Sodium (+-)-5-ethyl-5-(1-methylbutyl)-2-thiobarbiturate

25. Intraval Sodium

26. Nesdonal Sodium

27. Thiothal Sodium

28. Trapanal Sodium

29. Pentothal Sodium

30. Tiopental Sodium

31. Dsstox_cid_1744

32. Thiomebumalnatrium

33. Thiopenton-natrium

34. Dsstox_rid_76302

35. Sodium 5-ethyl-4,6-dioxo-5-(pentan-2-yl)-1,4,5,6-tetrahydropyrimidine-2-thiolate

36. Soluble Thiopentone

37. Dsstox_gsid_21744

38. Thiopentalum-natrium

39. Thiopentobarbitone Sodium

40. Thiopentalum Solubile

41. Sodium Penthiobarbital

42. Thiopental Sodium Salt

43. Tiopentale Sodico

44. Tiopentale Sodico [dcit]

45. Cas-71-73-8

46. 49y44qzl70

47. Tiopental Sodico [inn-spanish]

48. Thiopental Sodique [inn-french]

49. Nsc-759557

50. Thiopental, Sodium Salt

51. Thiopentalum Natricum [inn-latin]

52. Ncgc00159524-01

53. Einecs 200-763-1

54. Unii-49y44qzl70

55. Pentothal (tn)

56. Thiopental Sodium [usp:inn:jan]

57. 4,6(1h,5h)-pyrimidinedione, 5-ethyldihydro-5-(1-methylbutyl)-2-thioxo-, Monosodium Salt

58. 5-ethyl-5-(1-methylbutyl)-2-thiobarbituric Acid Monosodium

59. Chembl738

60. Schembl34621

61. Spectrum1900005

62. Dtxsid1021744

63. Hms503g07

64. Hms2094g03

65. Barbituric Acid, 5-ethyl-5-(1-methylbutyl)-2-thio-, Sodium Salt

66. Tox21_111741

67. Ccg-39536

68. Thiopental Sodium (jp17/usp/inn)

69. Akos025392174

70. Akos037653994

71. Tox21_111741_1

72. Ks-1432

73. Nsc 759557

74. Sodium 5-ethyl-5-(1-methylbutyl)-4,6-dioxo-1,4,5,6-tetrahydropyrimidine-2-thiolate

75. Ncgc00095773-01

76. Ncgc00159524-02

77. 4,6(1h,5h)-pyrimidinedione, 5-ethyldihydro-5-(1-methylbutyl)-2-thioxo-, Monosodium Salt, (+-)-

78. D00714

79. Q410179

2.3 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₇N₂NaO₂S
Molecular Weight	264.32 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	264.09084324 g/mol
Monoisotopic Mass	264.09084324 g/mol
Topological Polar Surface Area	59.5 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	346
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anesthetics, Intravenous

Ultrashort-acting anesthetics that are used for induction. Loss of consciousness is rapid and induction is pleasant, but there is no muscle relaxation and reflexes frequently are not reduced adequately. Repeated administration results in accumulation and prolongs the recovery time. Since these agents have little if any analgesic activity, they are seldom used alone except in brief minor procedures. (From AMA Drug Evaluations Annual, 1994, p174) (See all compounds classified as Anesthetics, Intravenous.)

Anticonvulsants

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

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.)

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API Reference Price

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