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Chemistry

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Also known as: Amytal sodium, 64-43-7, Amobarbital sodium [usp], Sodium 5-ethyl-5-(3-methylbutyl)-4,6-dioxo-1,4,5,6-tetrahydropyrimidin-2-olate, Amobarbital sodium for injection, Sodium 5-ethyl-5-isopentylbarbiturate

Molecular Formula

C₁₁H₁₇N₂NaO₃

Molecular Weight

248.25 g/mol

InChI Key

BNHGKKNINBGEQL-UHFFFAOYSA-M

A barbiturate with hypnotic and sedative properties (but not antianxiety). Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high. (From Martindale, The Extra Pharmacopoeia, 30th ed, p565)

1 2D Structure

Amobarbital Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;5-ethyl-5-(3-methylbutyl)-4,6-dioxo-1H-pyrimidin-2-olate

2.1.2 InChI

InChI=1S/C11H18N2O3.Na/c1-4-11(6-5-7(2)3)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

BNHGKKNINBGEQL-UHFFFAOYSA-M

2.1.4 Canonical SMILES

CCC1(C(=O)NC(=NC1=O)[O-])CCC(C)C.[Na+]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Amobarbital

2. Amobarbital, Sodium

3. Amsal

4. Amylbarb Sodium

5. Amylobarbitone

6. Amylobeta

7. Amytal

8. Amytal Sodium

9. Barbamyl

10. Eunoctal

11. Isoamitil Sedante

12. Isonal

13. Neur-amyl

14. Novamobarb

15. Pentymal

16. Placidel

17. Sodium Amobarbital

18. Sodium Amytal

19. Sodium, Amobarbital

20. Transital

2.2.2 Depositor-Supplied Synonyms

1. Amytal Sodium

2. 64-43-7

3. Amobarbital Sodium [usp]

4. Sodium 5-ethyl-5-(3-methylbutyl)-4,6-dioxo-1,4,5,6-tetrahydropyrimidin-2-olate

5. Amobarbital Sodium For Injection

6. Sodium 5-ethyl-5-isopentylbarbiturate

7. Alitinal

8. Amsebarb

9. Barbamylum

10. Dorminal

11. Dusotal

12. Inmetal

13. Sodium Barbamyl

14. Amytal Elixier

15. Amytal Sodique

16. Sodium Amytal

17. Robarb Kapseln

18. Lysmidone Sodico

19. Amobarbital Spota

20. T-barb

21. Sodium Amobarbital

22. Amobarbital Natrium

23. Amobarbital Sodium Salt

24. Sodium Amylobarbitone

25. 2,4,6(1h,3h,5h)-pyrimidinetrione, 5-ethyl-5-(3-methylbutyl)-, Monosodium Salt

26. Sodium;5-ethyl-5-(3-methylbutyl)-4,6-dioxo-1h-pyrimidin-2-olate

27. G0313knc7d

28. Dea No. 2125

29. Amylobarbitone, Sodium Deriv

30. Sodium Ethylisoamylbarbiturate

31. Sodium Isoamylethyl Barbiturate

32. Iso-amylaethylbarbitursaeures Natrium

33. Einecs 200-584-9

34. Unii-g0313knc7d

35. 5-ethyl-5-isopentylbarbituric Acid Sodium Salt

36. 5-isoamyl-5-ethylbarbituric Acid, Sodium Deriv

37. Amytal Sodium (tn)

38. 5-ethyl-5-(3-methylbutyl)barbituric Acid Sodium Derivative

39. 5-ethyl-5-(3-methylbutyl)-2,4,6-(1h,3h,5h)-pyrimidinetrione Sodium Salt

40. Barbituric Acid, 5-ethyl-5-isopentyl-, Sodium Salt

41. Amobarbital Sodium (jan/usp)

42. Barbituric Acid, 5-ethyl-5-isopentyl-, Sodium Deriv.

43. Chembl2105941

44. Schembl10335721

45. Dtxsid40213975

46. Bcp31728

47. Amytal Sodium; Sodium Amylobarbitone

48. Akos015962211

49. Ac-16079

50. Ft-0757237

51. D02252

52. Q27278414

2.3 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₇N₂NaO₃
Molecular Weight	248.25 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	248.11368669 g/mol
Monoisotopic Mass	248.11368669 g/mol
Topological Polar Surface Area	81.6 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	342
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	2

4 Pharmacology and Biochemistry

4.1 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.)

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