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Thiamylal

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Chemistry

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Also known as: Sodium thiamylal, Thiamylal sodium salt, 337-47-3, Surital sodium salt, Ncgc00095772-01, 5-allyl-5-(1-methylbutyl)-2-thiobarbituric acid, sodium salt

Molecular Formula

C₁₂H₁₇N₂NaO₂S

Molecular Weight

276.33 g/mol

InChI Key

LYZGJWXNOGIVQA-UHFFFAOYSA-M

A barbiturate that is administered intravenously for the production of complete anesthesia of short duration, for the induction of general anesthesia, or for inducing a hypnotic state. (From Martindale, The Extra Pharmacopoeia, 30th ed, p919)

1 2D Structure

Thiamylal

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C12H18N2O2S.Na/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16;/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17);/q;+1/p-1

2.1.3 InChI Key

LYZGJWXNOGIVQA-UHFFFAOYSA-M

2.1.4 Canonical SMILES

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

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Sodium, Thiamylal

2. Surital

3. Thiamylal

4. Thioquinalbarbitone

2.2.2 Depositor-Supplied Synonyms

1. Sodium Thiamylal

2. Thiamylal Sodium Salt

3. 337-47-3

4. Surital Sodium Salt

5. Ncgc00095772-01

6. 5-allyl-5-(1-methylbutyl)-2-thiobarbituric Acid, Sodium Salt

7. Surital Sodium

8. Thiomylal Sodium

9. Sodium 5-allyl-5-(1-methylbutyl)-2-thiobarbiturate

10. Thioseconal Sodium

11. T4l2p3kh7k

12. 5-allyl-5-(1-methylbutyl)-2-thiobarbituric Acid, Sodium Derivative

13. Surital Sodium Deriv.

14. Nsc-759558

15. 4,6-(1h,5h)-pyrimidinedione, Dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-, Monosodium Salt

16. Einecs 206-415-5

17. Unii-t4l2p3kh7k

18. Thiamylal Sodium [usp:jan]

19. Surital (tn)

20. 5-allyl-5-(1-methylbutyl)-2-thiobarbiturate Sodium

21. 5-allyl-5-(1-methylbutyl)-2-thio-barbituric Acid Sodium Salt

22. Thiamylal Sodium (jp17)

23. Dsstox_cid_25988

24. Dsstox_rid_81275

25. Dsstox_gsid_45988

26. Schembl34746

27. Spectrum1900002

28. Chebi:9537

29. Chembl1201065

30. Dtxsid3045988

31. Hms503e21

32. Hms2094g05

33. Tox21_111517

34. Barbituric Acid, 5-allyl-5-(1-methylbutyl)-2-thio-, Sodium Salt

35. Ccg-213640

36. Nsc 759558

37. Ncgc00095772-02

38. 4,6(1h,5h)-pyrimidinedione, Dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-, Monosodium Salt

39. Cas-337-47-3

40. D00713

41. Q27289664

2.3 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₇N₂NaO₂S
Molecular Weight	276.33 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	5
Exact Mass	276.09084324 g/mol
Monoisotopic Mass	276.09084324 g/mol
Topological Polar Surface Area	59.5 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	384
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.)

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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