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Chemistry

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Also known as: Methyl sulfide, 75-18-3, Methane, thiobis-, Dimethyl sulphide, Dimethylsulfide, Methyl thioether
Molecular Formula
C2H6S
Molecular Weight
62.14  g/mol
InChI Key
QMMFVYPAHWMCMS-UHFFFAOYSA-N
FDA UNII
QS3J7O7L3U

Dimethyl sulfide
Dimethyl sulfide is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

Dimethyl sulfide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
methylsulfanylmethane
2.1.2 InChI
InChI=1S/C2H6S/c1-3-2/h1-2H3
2.1.3 InChI Key
QMMFVYPAHWMCMS-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CSC
2.2 Other Identifiers
2.2.1 UNII
QS3J7O7L3U
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Dimethylsulphide

2.3.2 Depositor-Supplied Synonyms

1. Methyl Sulfide

2. 75-18-3

3. Methane, Thiobis-

4. Dimethyl Sulphide

5. Dimethylsulfide

6. Methyl Thioether

7. Dimethyl Thioether

8. Dimethylsulphide

9. 2-thiapropane

10. Methyl Sulphide

11. Methylthiomethane

12. Dimethylsulfid

13. (methylsulfanyl)methane

14. Methylsulfanylmethane

15. Methyl Monosulfide

16. Dimethyl Monosulfide

17. Thiobismethane

18. 2-thiopropane

19. Methanethiomethane

20. Thiobis(methane)

21. Exact-s

22. Sulfure De Methyle

23. Dimethyl Sulfide (natural)

24. Dimethylsulfane

25. Fema No. 2746

26. Methylthiomethyl Radical

27. Methane, 1,1'-thiobis-

28. [sme2]

29. Qs3j7o7l3u

30. Chebi:17437

31. (ch3)2s

32. Methylsulfide

33. Dimethylsulfid [czech]

34. Sulfure De Methyle [french]

35. Hsdb 356

36. Einecs 200-846-2

37. Mfcd00008562

38. Un1164

39. Unii-qs3j7o7l3u

40. Brn 1696847

41. Methylsulphide

42. Thiopropane

43. Thiobis-methane

44. Di-methylsulfide

45. Ai3-25274

46. Dimethyl Sulfane

47. Sulfide, Methyl-

48. (methylthio)methane

49. Me2s

50. Reduced-dmso

51. Sme2

52. Nat. Dimethyl Sulfide

53. Dimethyl Sulfide, 98%

54. Reduced Dimethyl Sulfoxide

55. (methylsulfanyl)methane #

56. Dimethyl Sulfide [un1164] [flammable Liquid]

57. Dimethyl Sulfide-[13c2]

58. Dimethyl Sulfoxide(reduced)

59. Ec 200-846-2

60. (me)2s

61. Dimethyl Sulfide, >=99%

62. (methylthiomethylidyne)radical

63. 4-01-00-01275 (beilstein Handbook Reference)

64. Chembl15580

65. Dimethyl Sulfide [mi]

66. Methyl Sulfide [fhfi]

67. Dimethyl Sulfide [fcc]

68. Dimethyl Sulfide [hsdb]

69. Dtxsid9026398

70. S(ch3)2

71. Dimethyl Sulfide, >=99%, Fcc

72. Dimethyl Sulfide, Analytical Standard

73. Stl481894

74. Dimethyl Sulfide, >=95.0% (gc)

75. Akos009031411

76. Un 1164

77. Dimethyl Sulfide, Anhydrous, >=99.0%

78. 31533-72-9

79. M0431

80. Dimethyl Sulfide, Puriss., >=99.0% (gc)

81. C00580

82. Dimethyl Sulfide, Natural, >=99%, Fcc, Fg

83. Dimethyl Sulfide [un1164] [flammable Liquid]

84. A838342

85. Dimethyl Sulfide, Redistilled, >=99%, Fcc, Fg

86. Q423133

87. Q-100810

88. Methyl Sulphide, Dimethyl Sulphide, Exact-s, Thiobismethane

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 62.14 g/mol
Molecular Formula C2H6S
XLogP30.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass62.01902136 g/mol
Monoisotopic Mass62.01902136 g/mol
Topological Polar Surface Area25.3 Ų
Heavy Atom Count3
Formal Charge0
Complexity2.8
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

Dimethyl sulfide is excreted by the lungs and the kidneys. Rats given oral or parenteral doses showed dimethyl sulfide in the breath. Dimethyl sulfide is also found in the breath of cats and mice given dimethylsulfoxide.

American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's with Other World Wide Occupational Exposure Values. CD-ROM Cincinnati, OH 45240-1634 2007.


Dimethyl sulfide was detected in milk from mature cows in late lactation following ingestion of capsules containing either 60 or 80 g of D,L-methionine or 1,2,or 4 mL of dimethyl sulfide; no dimethyl sulfide was detected in the cows dosed with lower doses of D,L-methionine.

American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's with Other World Wide Occupational Exposure Values. CD-ROM Cincinnati, OH 45240-1634 2007.


Excess methyl sulfide is exhaled with carbon dioxide, if it occurs in excess and in free form.

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. 2084


... The ip administration of dimethyl disulfide resulted in its appearance in the expired breath of mice and much smaller amounts of both methanethiol and dimethyl sulfide. The ip administration of methanethiol resulted in its pulmonary excretion and that of dimethyl sulfide. Administration of dimethyl sulfide led to its appearance alone in expired breath. Mice pretreated with ammonium acetate and then injected with dimethyl disulfide excreted the same 3 compounds via the lungs as above, but there were complex changes in the proportions and in the time sequence of their appearance. The absolute amounts of all 3 were increased, and the peak excretion for each was delayed. The amount excreted as dimethyl sulfide was particularly increased.

Susman JL et al; Drug Chem Toxicol 1 (4): 327-338 (1978). Available from, as of November 18, 2009: https://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~3rHMi5:1


4.2 Metabolism/Metabolites

... To identify breath sulfur compounds causing halitosis induced by cysteamine therapy in patients with cystinosis. After the ingestion of 15 mg/kg cysteamine, whole blood (n = 4), urine (n = 4) and breath (n = 8) volatile sulfur compounds levels were measured every 60 min over a 360 min period by gas chromatography and the cysteamine plasma concentrations (n = 4) were measured by high-performance liquid chromatography. The expired air of cystinotic patients contained elevated concentrations of methanethiol (MT, median maximum value 0.5 (range 0-11) nmol/L) and, in particular, dimethyl sulfide (DMS, median maximum value 15 (range 2-83) nmol/L). DMS concentrations higher than 0.65 nmol/L are known to cause halitosis. Maximal plasma values of cysteamine (median 46 (range 30-52) umol/L) preceded those of MT and DMS, confirming that cysteamine is converted to MT and DMS. Less than 3% of the amount of cysteamine ingested was excreted as MT and DMS via expired air and 0.002% via urine. Halitosis induced by cysteamine intake is caused by DMS and to a lesser extent by MT, excreted via the expired air ...

PMID:17513151 Besouw M et al; Mol Genet Metab. 2007 Jul;91(3):228-33 (2007).


Dimethylsulfoxide and dimethylsulfdioxide were found in rabbit urine following dimethyl sulfide administration.

American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's with Other World Wide Occupational Exposure Values. CD-ROM Cincinnati, OH 45240-1634 2007.


The ip admin of dimethyl disulfide resulted in the appearance of dimethyl sulfide in expired breath of mice. Ip admin of methanethiol resulted in pulmonary excretion of dimethyl sulfide.

Susman JL et al; Drug Chem Toxicol 1 (4): 327-38 (1979)


Methyl sulfide introduced into the mammalian system by ingestion or inhalation at low quantities can readily be metabolized. ... Methyl sulfide can also be formed as a degradation product from dimethyl sulfoxide. ... It is also formed from S-methylcysteine sulfoxide by intestinal bacteria.

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. 2084


A single ip injection of 275 mg of dimethyl sulfoxide (DMSO) to rats effectively uncouples oxidative phosphorylation in liver mitochondria during the period from 2 hr to 5 days postinjection. Higher doses of DMSO are inhibitory to mitochondrial respiration. DMSO has, however, no uncoupling action on oxidative phosphorylation in vitro. Dimethyl sulfide, a known metabolite of DMSO, brings about the uncoupling effect in vitro. The uncoupling of oxidative phosphorylation by normal mitochondria could also be achieved if these are preincubated with postmitochondrial liver supernatant derived from rat injected with DMSO, 2-24 hr prior to sacrifice. These results provide an explanation for the observed uncoupling effect exerted by DMSO in vivo.

PMID:6838520 Mhatre SS et al; Biochem Biophys Res Commun 110 (1): 325-31 (1983)


4.3 Biological Half-Life

After overnight fasting, the concn of dimethyl sulfide in expired alveolar gas (ALV-DMS) was determined serially following ingestion of 2 g of dl-methionine in normal subjects and pt with liver diseases. ALV-DMS peaked in 30-90 min, declined markedly in 3 hr. Cirrhotics had t/2 longer than any other group.

PMID:445853 Kaji H et al; Clin Chim Acta 93 (3): 377-80 (1979)


4.4 Mechanism of Action

A single ip injection of 275 mg of dimethyl sulfoxide (DMSO) to rats effectively uncouples oxidative phosphorylation in liver mitochondria during the period from 2 hr to 5 days postinjection. Higher doses of DMSO are inhibitory to mitochondrial respiration. DMSO has, however, no uncoupling action on oxidative phosphorylation in vitro. Dimethyl sulfide, a known metabolite of DMSO, brings about the uncoupling effect in vitro. The uncoupling of oxidative phosphorylation by normal mitochondria could also be achieved if these are preincubated with postmitochondrial liver supernatant derived from rat injected with DMSO, 2-24 hr prior to sacrifice. These results provide an explanation for the observed uncoupling effect exerted by DMSO in vivo.

PMID:6838520 Mhatre SS et al; Biochem Biophys Res Commun 110 (1): 325-31 (1983)


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28-Jan-2021
22-Oct-2024
KGS
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Average Price (USD/KGS)

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Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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