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2D Structure
Also known as: 55406-53-6, Iodopropynyl butylcarbamate, Ipbc, Woodlife, Troysan kk-108a, Caswell no. 501a
Molecular Formula
C8H12INO2
Molecular Weight
281.09  g/mol
InChI Key
WYVVKGNFXHOCQV-UHFFFAOYSA-N
FDA UNII
603P14DHEB

RN & structure given in first source
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-iodoprop-2-ynyl N-butylcarbamate
2.1.2 InChI
InChI=1S/C8H12INO2/c1-2-3-6-10-8(11)12-7-4-5-9/h2-3,6-7H2,1H3,(H,10,11)
2.1.3 InChI Key
WYVVKGNFXHOCQV-UHFFFAOYSA-N
2.2 Other Identifiers
2.2.1 UNII
603P14DHEB
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-iodo-2-propynylbutylcarbamate

2. 3-ipbc

3. 3-iodo-2-propynyl-butylcarbamate

4. Iodopropynyl Butylcarbamate

2.3.2 Depositor-Supplied Synonyms

1. 55406-53-6

2. Iodopropynyl Butylcarbamate

3. Ipbc

4. Woodlife

5. Troysan Kk-108a

6. Caswell No. 501a

7. Butyl-3-iodo-2-propynylcarbamate

8. 3-iodo-2-propynyl Butyl Carbamate

9. 3-iodoprop-2-yn-1-yl N-butylcarbamate

10. 603p14dheb

11. 3-iodo-2-propyn-1-yl N-butylcarbamate

12. Carbamic Acid, Butyl-3-iodo-2-propynyl Ester

13. 3-iodoprop-2-ynyl Butylcarbamate

14. 3-ipbc

15. 3-iodo-2-propynyl-butylcarbamate

16. Refchem:502679

17. Iodopropynyl Butyl Carbamate

18. 259-627-5

19. 3-iodo-2-propynylbutylcarbamate

20. 3-iodoprop-2-yn-1-yl Butylcarbamate

21. Iodocarb

22. 3-iodo-2-propynyl N-butylcarbamate

23. 3-iodoprop-2-ynyl N-butylcarbamate

24. Carbamic Acid, Butyl-, 3-iodo-2-propynyl Ester

25. 1-iodoprop-1-yn-3-yl N-n-butylcarbamate

26. 3-iodo-2-propynyl-n-butylcarbamate

27. Mfcd00072438

28. C8h12ino2

29. Dtxsid0028038

30. Chebi:83279

31. 85045-09-6

32. Dtxcid908038

33. Cas-55406-53-6

34. 3-iodo-2-propynyl N-butylcarbamate-d9

35. Hsdb 7314

36. Einecs 259-627-5

37. Epa Pesticide Chemical Code 107801

38. Brn 2248232

39. Iodocarbe

40. Unii-603p14dheb

41. 3-iodo-2-propynyl-n-butyl Carbamate

42. 1246815-08-6

43. Iodocarb 100 Microg/ml In Acetonitrile

44. 3-iodo-2-propynylbutyl Carbamate

45. Ipbc [mi]

46. Schembl114369

47. Chembl1893913

48. 3-iodo-2-propynyl Butylcarbamate #

49. 3-iodoprop-2-yn-1-ylbutylcarbamate

50. Tox21_201864

51. Tox21_301117

52. Akos015905567

53. Cs-w010051

54. Fi16109

55. Gs-3240

56. Ncgc00164376-01

57. Ncgc00164376-02

58. Ncgc00164376-03

59. Ncgc00164376-04

60. Ncgc00164376-05

61. Ncgc00255017-01

62. Ncgc00259413-01

63. Sy052464

64. 3-iodo-2-propynyl N-butylcarbamate, 97%

65. Iodopropynyl Butylcarbamate [vandf]

66. 3-iodo-2-propynyl Butyl Carbbamate

67. Db-262370

68. I0666

69. Iodopropynyl Butyl Carbamate [mart.]

70. Ns00000275

71. N-butylcarbamic Acid 3-iodo-2-propynyl Ester

72. 06i536

73. 3-iodo-2-propynylbutylcarbamate [hsdb]

74. F050829

75. Q2928998

76. Carbamic Acid, N-butyl-, 3-iodo-2-propyn-1-yl Ester

77. 3-iodo-2-propynyl N-butylcarbamate, Analytical Standard

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 281.09 g/mol
Molecular Formula C8H12INO2
XLogP32.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass Da
Monoisotopic Mass Da
Topological Polar Surface Area38.3
Heavy Atom Count12
Formal Charge0
Complexity192
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

...IPBC was administered orally in 0.5% carboxymethylcellulose to groups of male and female Crl:CD/BR rats in the following manner: Groups of 5 male and 5 female rats (groups A and B) received either a single oral high dose of radiolabelled IPBC (125 mg/kg) or a repeated low oral dose of non-radiolabelled IPBC followed by a single radiolabelled dose (20 mg/kg). Separate groups of rats (9/sex/group, groups C and D) received single oral doses (20 and 125 mg/kg) of radiolabelled IPBC, and 3 rats/sex were sacrificed at 2, 4, and 120 hours post-dose for determination of tissue distribution of radioactivity. Urine, feces and expired air were collected at 24 hr intervals for groups A and B, while urine and feces were collected from groups C and D. Absorption of test chemical at the low and high dose was between 80-90% for all dose groups, as suggested by excretion data showing the majority of a dose eliminated through urine or exhaled air. Excretion of IPBC-derived radioactivity was mainly via the urine, with between 50-70% of an administered dose excreted by this route at 168 hours post-dose. Feces was a minor route of excretion in all dose groups (4-7% of the administered dose), while radiolabelled CO2 constituted between 18-24% of the administered dose. Repeated low oral dosing or a single high oral dose appeared to result in a decrease in the percentage of radioactivity excreted as 14-CO2 compared to a single low dose.

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - 3-Iodo-2-propynyl butylcarbamate(IPBC). EPA 738-R-97-003 March 1997. Available from, as of January 31, 2005: https://www.epa.gov/pesticides/reregistration/status.htm


4.2 Metabolism/Metabolites

...IPBC undergoes reductive dehalogenation followed by dealkylation to form the URM-9 and URM-10 metabolites. In addition, de-carboxylation following reductive dehalogenation yields carbon dioxide. Various other metabolites formed from dehalogenation are glucuronidated and constitute minor metabolites of IPBC.

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - 3-Iodo-2-propynyl butylcarbamate(IPBC). EPA 738-R-97-003 March 1997. Available from, as of January 31, 2005: https://www.epa.gov/pesticides/reregistration/status.htm


The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)