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Isoamyl Nitrite

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Chemistry

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Also known as: Isopentyl nitrite, 110-46-3, 3-methylbutyl nitrite, Amilnitrite, Vaporole, Nitrous acid, 3-methylbutyl ester

Molecular Formula

C₅H₁₁NO₂

Molecular Weight

117.15 g/mol

InChI Key

OWFXIOWLTKNBAP-UHFFFAOYSA-N

FDA UNII

5N0U5TUC9Z

1 2D Structure

Isoamyl Nitrite

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-methylbutyl nitrite

2.1.2 InChI

InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3

2.1.3 InChI Key

OWFXIOWLTKNBAP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)CCON=O

2.2 Other Identifiers

2.2.1 UNII

5N0U5TUC9Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Isopentyl Nitrite

2.3.2 Depositor-Supplied Synonyms

1. Isopentyl Nitrite

2. 110-46-3

3. 3-methylbutyl Nitrite

4. Amilnitrite

5. Vaporole

6. Nitrous Acid, 3-methylbutyl Ester

7. 3-methylbutanol Nitrite

8. Aspiral

9. Pentanoli Nitris

10. Nitrous Acid, Isopentyl Ester

11. Amyl Nitrite I

12. Nitramyl (van)

13. Isopentyl Alcohol, Nitrite

14. Amyl Nitrite (van)

15. Amyl Nitrite [usan]

16. Isoamylnitrite

17. Iso-amylnitrite

18. Iso-amyl Nitrite

19. Nsc 7903

20. Vaporole (tn)

21. Aspiral (tn)

22. 5n0u5tuc9z

23. Chebi:2691

24. Nci-c50179

25. Nsc-7903

26. Mfcd00002057

27. Ncgc00091066-01

28. Dsstox_cid_2605

29. Dsstox_rid_77794

30. Dsstox_gsid_25455

31. Amyl Nitrit

32. Cas-110-46-3

33. Ccris 1098

34. Hsdb 606

35. Einecs 203-770-8

36. Unii-5n0u5tuc9z

37. Amyl Nitrite, Mixed Isomers

38. Brn 0969510

39. Isopentylnitrit

40. Amylnitrit

41. Isoamyinitrite

42. Isopentylnitrite

43. Ai3-25183

44. Nitrous Acid 3-methylbutyl Ester

45. Nitrous Acid Isoamyl

46. Vaporole Amyl Nitrite

47. Nitrite Isopentyl Alcohol

48. Isopentyl Nitrite, 96%

49. Wln: Ono2y

50. Amyl Nitrite [jan]

51. Amyl Nitrite(mixed Isomers)

52. 3-methyl-1-nitrosooxybutane

53. Isopentyl Ester Nitrous Acid

54. Amyl Nitrite [hsdb]

55. Schembl23785

56. Amyl Nitrite (jp15/usp)

57. Amyl Nitrite (jp17/usp)

58. Isoamyl Nitrite [mi]

59. 3-methyl-1-nitrosooxy-butane

60. Chembl1535371

61. Dtxsid9025455

62. Amy3781

63. Isoamyl Nitrite 97%, Stabilized

64. Nsc7903

65. Act05198

66. Zinc3830220

67. Tox21_111074

68. Tox21_200983

69. Stl264239

70. Akos009157290

71. Isopentyl Nitrite, >=97.0% (gc)

72. Wt82484

73. Ncgc00091066-02

74. Ncgc00258536-01

75. Ls-13086

76. Db-002757

77. Ft-0627442

78. I0089

79. C07457

80. D00517

81. Sr-01000944365

82. J-802226

83. Sr-01000944365-1

84. Q27888090

85. F0001-0219

86. Isoamyl Nitrite, Stab. With 0.2% Anhyd. Sodium Carbonate

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₅H₁₁NO₂
Molecular Weight	117.15 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	117.078978594 g/mol
Monoisotopic Mass	117.078978594 g/mol
Topological Polar Surface Area	38.7 Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	63.4
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

...In emergency treatment of cyanide poisoning... for this purpose, sodium nitrite is employed iv, but amyl nitrite may be inhaled while solution of sodium nitrite is being prepared.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 788

In angina pectoris, pain is eased by vasodilation of coronary arteries produced by amyl nitrite.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 788

Basic pharmacological action of nitrites is to relax smooth muscle. Relaxation is nonspecific... /nitrites/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 728

Amyl nitrite also has been used to produce changes in the intensity of heart murmurs. Murmurs resulting from stenosis of any of the 4 cardiac valves or from idiopathic hypertrophic subaortic stenosis will become louder after amyl nitrite administration. Murmurs resulting from aortic or mitral regurgitation usually decrease in intensity.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1879

For more Therapeutic Uses (Complete) data for ISOAMYL NITRITE (8 total), please visit the HSDB record page.

4.2 Drug Warning

The nitrates and nitrites should be used with caution, if at all, in patients with increased intracranial pressure (e.g., head trauma, cerebral hemorrhage) and are contraindicated in patients with severe anemia or with a previous idiosyncratic or hypersensitivity reaction to these drugs. /Nitrates and nitrites/

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1876

Since amyl nitrite increases intraocular pressure as well as that of cerebrospinal fluid, it should be used with caution in pt with glaucoma or cerebral hemorrhage.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 24:12

Headache, the most frequent adverse effect may be severe (persistent or transient) and is perceived as a pulsating, throbbing sensation; headache is especially common after inhalation of amyl nitrite. /Nitrates and nitrites/

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1875

VET: Causes intense and rapid lowering of blood pressure and increases in heart rate.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 19

For more Drug Warnings (Complete) data for ISOAMYL NITRITE (7 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

Amyl nitrite is readily absorbed via the respiratory tract...

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1878

Approx 1/3 of the inhaled amy nitrite is excreted in the urine.

Medical Economics Co; Physicians Desk Reference- Generics 2nd ed p.212 (1996)

5.2 Metabolism/Metabolites

Amyl nitrite ... probably is rapidly hydrolyzed to isoamyl alcohol and nitrite ion.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1878

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