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2D Structure
Also known as: Immenoctal, Pramil, Sebar, Synate, Evronal sodium, Quinalbarbitone sodium
Molecular Formula
C12H17N2NaO3
Molecular Weight
260.26  g/mol
InChI Key
AXXJTNXVUHVOJW-UHFFFAOYSA-M
FDA UNII
XBP604F6UM

A barbiturate that is used as a sedative. Secobarbital is reported to have no anti-anxiety activity.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;5-pentan-2-yl-5-prop-2-enylpyrimidin-3-ide-2,4,6-trione
2.1.2 InChI
InChI=1S/C12H18N2O3.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
AXXJTNXVUHVOJW-UHFFFAOYSA-M
2.1.4 Canonical SMILES
CCCC(C)C1(C(=O)NC(=O)[N-]C1=O)CC=C.[Na+]
2.2 Other Identifiers
2.2.1 UNII
XBP604F6UM
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Meballymal

2. Quinalbarbitone

3. Sebar

4. Secobarbital

5. Seconal

6. Seconal Sodium

7. Sodium, Secobarbital

2.3.2 Depositor-Supplied Synonyms

1. Immenoctal

2. Pramil

3. Sebar

4. Synate

5. Evronal Sodium

6. Quinalbarbitone Sodium

7. Barbosec

8. Sodium Seconal

9. Sodium Secobarbital

10. 309-43-3

11. Bipanal

12. Evrronal

13. Imesonal

14. Quinalspan

15. Sedutain

16. Trisomnin

17. Bipinal Sodium

18. Seconal Sodium

19. Meballymal Sodium

20. Seco 8

21. Sodium Quinalbarbitone

22. (rs)-secobarbital Sodium

23. Xbp604f6um

24. 5-allyl-5-(1-methylbutyl)barbituric Acid Sodium Salt

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

26. Nsc-10818

27. 5-(1-methylbutyl)-5-(2-propenyl)-2,4,6(1h,3h,5h)-pyrimidinetrione Monosodium Salt

28. Dea No. 2315

29. Sodium 5-allyl-5-(1-methylbutyl)barbiturate

30. Dormatylan

31. Dormona

32. 5-allyl-5-(1-methylbutyl)malonylurea Sodium Salt

33. Barbituric Acid, 5-allyl-5-(1-methylbutyl)-, Sodium Salt

34. Secobarbitone Sodium

35. Einecs 206-218-4

36. Nsc 10818

37. Secobarbital Sodium [jan]

38. Unii-xbp604f6um

39. Propylmethylcarbinylallyl Barbituric Acid Sodium Salt

40. Seconal Sodium (tn)

41. Secobarbital Sodium [usp:inn:ban:jan]

42. Secobarbital Sodium (jan/usp)

43. Chembl1200903

44. Secobarbital Sodium [mi]

45. Secobarbital Sodium [vandf]

46. Secobarbital Sodium [mart.]

47. Secobarbital Sodium [who-dd]

48. Secobarbital Sodium [green Book]

49. Secobarbital Sodium [orange Book]

50. Secobarbital Sodium [usp Impurity]

51. Secobarbital Sodium [usp Monograph]

52. D01310

53. Q27293769

54. Sodium;5-pentan-2-yl-5-prop-2-enylpyrimidin-3-ide-2,4,6-trione

55. 2,4,6(1h,3h,5h)-pyrimidinetrione, 5-(1-methylbutyl)-5-(2-propen-1-yl)-, Sodium Salt (1:1)

2.4 Create Date
2007-02-09
3 Chemical and Physical Properties
Molecular Weight 260.26 g/mol
Molecular Formula C12H17N2NaO3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass260.11368669 g/mol
Monoisotopic Mass260.11368669 g/mol
Topological Polar Surface Area64.2 Ų
Heavy Atom Count18
Formal Charge0
Complexity370
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameSeconal sodium
PubMed HealthSecobarbital (By mouth)
Drug ClassesSedative
Drug LabelThe barbiturates are nonselective central nervous system (CNS) depressants that are primarily used as sedative hypnotics. In subhypnotic doses, they are also used as anticonvulsants. The barbiturates and their sodium salts are subject to control unde...
Active IngredientSecobarbital sodium
Dosage FormCapsule
RouteOral
Strength100mg; 50mg
Market StatusPrescription
CompanyMarathon Pharms

2 of 2  
Drug NameSeconal sodium
PubMed HealthSecobarbital (By mouth)
Drug ClassesSedative
Drug LabelThe barbiturates are nonselective central nervous system (CNS) depressants that are primarily used as sedative hypnotics. In subhypnotic doses, they are also used as anticonvulsants. The barbiturates and their sodium salts are subject to control unde...
Active IngredientSecobarbital sodium
Dosage FormCapsule
RouteOral
Strength100mg; 50mg
Market StatusPrescription
CompanyMarathon Pharms

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Adjuvants, Anesthesia

Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage. (See all compounds classified as Adjuvants, Anesthesia.)


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.)