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2D Structure
Also known as: N-butane, 106-97-8, Diethyl, R 600 (alkane), Hc 600 (hydrocarbon), Methylethylmethane
Molecular Formula
C4H10
Molecular Weight
58.12  g/mol
InChI Key
IJDNQMDRQITEOD-UHFFFAOYSA-N
FDA UNII
6LV4FOR43R

butane is a natural product found in Stemona tuberosa and Calendula officinalis with data available.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
butane
2.1.2 InChI
InChI=1S/C4H10/c1-3-4-2/h3-4H2,1-2H3
2.1.3 InChI Key
IJDNQMDRQITEOD-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCC
2.2 Other Identifiers
2.2.1 UNII
6LV4FOR43R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. N-butane

2.3.2 Depositor-Supplied Synonyms

1. N-butane

2. 106-97-8

3. Diethyl

4. R 600 (alkane)

5. Hc 600 (hydrocarbon)

6. Methylethylmethane

7. Butanen

8. Butani

9. Hc 600

10. R 600

11. Butane [nf]

12. Butane-silver

13. 6lv4for43r

14. E943a

15. N-c4h10

16. Ins No.943

17. Butane Phase Ii

18. Chebi:37808

19. Ins-943

20. Butane (nf)

21. Butan

22. Butyl Hydride

23. E-943

24. Butane, Pure

25. Butanen [dutch]

26. Butani [italian]

27. Butane (d10)

28. Butane (1-d1)

29. Butane (2-d1)

30. A 21 (lowing Agent)

31. Ccris 2279

32. Hsdb 944

33. Hydrocarbons, C1-4

34. Hydrocarbons, C4-5

35. Einecs 203-448-7

36. Un1011

37. Unii-6lv4for43r

38. N-butan

39. 1,2-dimethyethane

40. 1,2-dimethylethane

41. 1,2-dimethyl-ethane

42. Butane, 99%

43. Freon 600

44. Butane [hsdb]

45. Butane [inci]

46. Butane [fcc]

47. Butane [who-dd]

48. Butane Or Butane Mixtures

49. Butane [ii]

50. Butane [mi]

51. Butane [mart.]

52. N-butane;methylethylmethane

53. Ec 203-448-7

54. Chembl134702

55. H-c4h9

56. Dtxsid7024665

57. E 943a

58. E-943a

59. Bcp32076

60. Zinc8214510

61. Butane 2000 Microg/ml In Methanol

62. Mfcd00009424

63. Akos015917446

64. Akos032949915

65. Zinc256080833

66. Zinc306122401

67. Un 1011

68. 68476-42-6

69. 68514-31-8

70. B0677

71. Ft-0770500

72. R-600

73. C21390

74. D03186

75. Q134192

76. Butane Or Butane Mixtures [un1011] [flammable Gas]

77. Butane, Fuel For Micro Torch, Contains No Cfc Gases

78. 06005800-a997-4214-bf1c-5063e9e46167

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 58.12 g/mol
Molecular Formula C4H10
XLogP32.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count1
Exact Mass58.078250319 g/mol
Monoisotopic Mass58.078250319 g/mol
Topological Polar Surface Area0 Ų
Heavy Atom Count4
Formal Charge0
Complexity2
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

Inhalation studies ... in which rats and mice were exposed to lethal concn (27.8-29%) revealed that n-butane is absorbed and distributed to various tissues. After 4 hr of respiratory exposure, surviving rats were sacrificed ... concn of butane were ... highest in perinephric fat (2086 ppm), then brain (750 ppm), spleen (522 ppm), liver (492 ppm), and kidney (441 ppm). In mice exposed to 2 hr of butane vapors, the brain levels of n-butane were found to be 779 ppm. In both rats and mice the brain levels of n-butane correlated with the degree of CNS depression ... Dermal absorption of n-butane vapors has not been reported. However, dermal penetration of butane would not be expected to occur to any large extent since skin contact is transient because of volatility.

Snyder, R. (ed.) Ethel Browning's Toxicity and Metabolism of Industrial Solvents. 2nd ed. Volume 1: Hydrocarbons. Amsterdam - New York - Oxford: Elsevier, 1987., p. 269


Because of its volatile nature, elimination of butane by exhalation can be anticipated.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V4 15


4.2 Metabolism/Metabolites

A study was conducted to establish whether volatile hydrocarbons, such as propane, n-butane and iso-butane, are metabolized in mice or not. In mice having inhaled these gases, isopropanol and acetone were yielded from propane, sec-butanol and methyl ethyl ketone from n-butane, and tert-butanol from iso-butane as the respective metabolites. In addition, liver microsomes were found to contain the enzymic system participating in these metabolisms. In vitro reactions with liver microsomes produced isopropanol from propane, sec-butanol from n-butane, and tert-butanol from iso-butane. It was assumed that hydrocarbons were first converted to (omega-1)-alcohols by microsomal enzyme system and then to corresponding ketones by alcohol dehydrogenase.

PMID:3913777 Tsukamoto S et al; J Toxicol Sci.10(4):323-32 (1985).


Microsomal enzyme systems have been found that oxidize butane to its parent alcohol.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 3183


Hydroxylation of butane ... /occurs/ in rat liver microsomes to yield 2-butanol as the major metabolite. n-Butane is the lowest molecular weight alkane ... demonstrated to substrate-bind with cytochrome p450. ... If 2-butanol is the major metabolite formed in mammals, it would be expected to be eliminated in expired air. ... 2-Butanol may also be conjugated with glucuronic acid or be oxidized to methyl ethyl ketone which in turn is expired.

Snyder, R. (ed.) Ethel Browning's Toxicity and Metabolism of Industrial Solvents. 2nd ed. Volume 1: Hydrocarbons. Amsterdam - New York - Oxford: Elsevier, 1987., p. 269


Purified liquefied petroleum gas (LPG), a mixture of butane, isobutane, and propane, is commonly abused by inhalation. Little is known about the mammalian metabolism of these substances. Metabolism of other hydrocarbons, including n-hexane and cyclohexane, has been studied in vitro using a range of liver preparations, with metabolites analyzed by static headspace techniques... Cyclohexanol and cyclohexanone were formed from cyclohexane and 1-, 2-, and 3-hexanol and 2-hexanone from n-hexane as predicted. Secondary alcohols are found for the other compounds studied, except for propene and isobutane, together with 2-propanone and 2-butanone from propane and n-butane, respectively. Samples from three individuals who died following LPG abuse contained a range of putative n-butane metabolites: n-butanol, 2-butanol, 2,3-butanediol, 3-hydroxy-2-butanone, and 2,3-butanedione. To /the authors/ knowledge, the last three compounds have not been proposed as metabolites of n-butane in man. These might be produced through similar metabolic pathways to those of n-hexane and n-heptane...

PMID:16925936 Walker R et al; J Chromatogr Sci. 44(7):387-93 (2006).


4.3 Biological Half-Life

Based on kinetic studies ... with ethane and n-pentane, the elimination half-life of n-butane can be expected to be closer to that of n-pentane (half life= 0.13 hr, at nonsaturating concn).

Snyder, R. (ed.) Ethel Browning's Toxicity and Metabolism of Industrial Solvents. 2nd ed. Volume 1: Hydrocarbons. Amsterdam - New York - Oxford: Elsevier, 1987., p. 269


Its elimination half-life is 0.13 hr at nonsaturating concns.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V4 15


4.4 Mechanism of Action

...Not infrequently intentional butane inhalation results in high morbidity and mortality. A fatal outcome of butane abuse can be caused by asphyxia, cardiac arrhythmia or trauma. The reported number of cases in which death was the consequence of pure butane inhalation is limited, and in most cases a mixture of propellants was involved. This report covers two cases of sudden death due to the sniffing of a cigarette lighter refill containing butane. Autopsy was followed by toxicological, pathohistological and immunohistochemical analysis. Butane gas was confirmed in samples of blood, urine, brain and lungs... Histology showed almost identical changes in the lungs and heart in both cases. The morphology of heart damage on standard H/E stains was of special interest because it displayed all the characteristics of chronic and acute myocardial hypoxia found in the absence of atherosclerotic heart disease. In order to confirm early cardiac death caused by asphyxia due to butane inhalation a panel of immunohistochemical agents was used...

PMID:21420651 Novosel I et al; J Forensic Leg Med. 18(3):125-31 (2011).