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Binapacryl

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ACTIVE PHARMA INGREDIENTS

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1 API Suppliers
1 USDMF

Synopsis

ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 485-31-4, Endosan, Dinapacryl, Acricid, Dapacryl, Morocide

Molecular Formula

C₁₅H₁₈N₂O₆

Molecular Weight

322.31 g/mol

InChI Key

ZRDUSMYWDRPZRM-UHFFFAOYSA-N

FDA UNII

4X685BB13A

1 2D Structure

Binapacryl

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2-butan-2-yl-4,6-dinitrophenyl) 3-methylbut-2-enoate

2.1.2 InChI

InChI=1S/C15H18N2O6/c1-5-10(4)12-7-11(16(19)20)8-13(17(21)22)15(12)23-14(18)6-9(2)3/h6-8,10H,5H2,1-4H3

2.1.3 InChI Key

ZRDUSMYWDRPZRM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCC(C)C1=C(C(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-])OC(=O)C=C(C)C

2.2 Other Identifiers

2.2.1 UNII

4X685BB13A

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Binapacrile

2. Binapakril

2.3.2 Depositor-Supplied Synonyms

1. 485-31-4

2. Endosan

3. Dinapacryl

4. Acricid

5. Dapacryl

6. Morocide

7. Morrocid

8. Ambox

9. Dinoseb Methacrylate

10. Niagara 9044

11. Hoe 2784 Oa

12. Dinoseb, 3,3-dimethylacryl Ester

13. 2-(1-methylpropyl)-4,6-dinitrophenyl 3-methyl-2-butenoate

14. Fmc 9044

15. Hoe 2784

16. Nia 9044

17. Ent 25,793

18. 2-sec-butyl-4,6-dinitrophenyl Senecioate

19. (2-butan-2-yl-4,6-dinitrophenyl) 3-methylbut-2-enoate

20. 2,4-dinitro-6-sec-butylphenyl 2-methylcrotonate

21. 2-sec-butyl-4,6-dinitrophenyl 3-methylcrotonate

22. 2-sec-butyl-4,6-dinitrophenyl 3-methyl-2-butenoate

23. 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate

24. 4,6-dinitrophenyl-2-sec-butyl-3-methyl-2-butenonate

25. 2-butenoic Acid, 3-methyl-, 2-(1-methylpropyl)-4,6-dinitrophenyl Ester

26. Phenol, 2-sec-butyl-4,6-dinitro-, 3-methylcrotonate

27. 3-methylcrotonic Acid 2-sec-butyl-4,6-dinitrophenyl Ester

28. 3,3-dimethylacrylic Acid 2-sec-butyl-4,6-dinitrophenyl Ester

29. 3-methyl-2-butenoic Acid 2-sec-butyl-4,6-dinitrophenyl Ester

30. Chebi:83366

31. Crotonic Acid, 3-methyl-, 2-sec-butyl-4,6-dinitrophenyl Ester

32. 3-methyl-2-butenoic Acid 2-(1-methylpropyl)-4,6-dinitrophenyl Ester

33. 4x685bb13a

34. 2-sek.butyl-4,6-dinitrofenylester Kyseliny 3-methylkrotonove

35. (6-(1-metil-propil)-2,4-dinitro-fenil)-3,3-dimetil-acrilato

36. (6-(1-methyl-propyl)-2,4-dinitro-fenyl)-3,3-dimethyl-acrylaat

37. (6-(1-methyl-propyl)-2,4-dinitro-phenyl)-3,3-dimethyl-acrylat

38. 3,3 Dimethyl-acrylate De 2,4-dinitro-6-(1-methylpropyle) Phenyle

39. 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate

40. Caswell No. 086

41. 4,6-dinitrophenyl-2-(1-methylpropyl) 3-methylbut-2-enoate

42. 2-butenoic Acid,3-methyl-, 2-(1-methylpropyl)-4,6-dinitrophenyl Ester

43. 2-butenoic Acid, 3-methyl-, 2-(1-methylpropyl)-4,6-dinitrophenyl Ester (9ci)

44. Binapacryl [ansi:bsi:iso]

45. Hsdb 1518

46. Einecs 207-612-9

47. Epa Pesticide Chemical Code 012201

48. Brn 2013712

49. Unii-4x685bb13a

50. Ai3-25793

51. Senecioic Acid 2-sec Butyl-4,6-dinitrophenyl Ester

52. Senecioic Acid 2-sec-butyl-4,6-dinitrophenyl Ester

53. 2-sec-butyl-4,6-dinitrophenyl Beta,beta-dimethylacrylate

54. 4,6-dinitro-2-sec-butylphenyl Beta,beta-dimethylacrylate

55. 2-(1-methylpropyl)-4,6-dinitrophenyl 3,3-dimethylacrylate

56. Binapacryl [mi]

57. 2-(1-methylpropyl)-4,6-dinitrophenyl Beta,beta-dimethacrylate

58. Binapacryl [iso]

59. Binapacryl [hsdb]

60. (6-(1-methyl-propyl)-2,4-dinitro-fenyl)-3,3-dimethyl-acrylaat [dutch]

61. (6-(1-metil-propil)-2,4-dinitro-fenil)-3,3-dimetil-acrilato [italian]

62. 2-sek.butyl-4,6-dinitrofenylester Kyseliny 3-methylkrotonove [czech]

63. (6-(1-methyl-propyl)-2,4-dinitro-phenyl)-3,3-dimethyl-acrylat [german]

64. 3,3 Dimethyl-acrylate De 2,4-dinitro-6-(1-methylpropyle) Phenyle [french]

65. 3,3 Dimethyl-acrylate De 2,4-dinitro-6-(1-methylpropyle)phenyl [french]

66. 3,3 Dimethyl-acrylate De 2,4-dinitro-6-(1-methylpropyle)phenyle [french]

67. Dsstox_cid_20269

68. Dsstox_rid_79462

69. Dsstox_gsid_40269

70. Schembl54301

71. Chembl3182974

72. Dtxsid9040269

73. Zrdusmywdrpzrm-uhfffaoysa-

74. 3,3 Dimethyl-acrylate De 2,4-dinitro-6-(1-methylpropyle)phenyl

75. 3,3 Dimethyl-acrylate De 2,4-dinitro-6-(1-methylpropyle)phenyle

76. Tox21_301554

77. Mfcd00055425

78. Akos015888368

79. Binapacryl 1000 Microg/ml In Hexane

80. Binapacryl 10 Microg/ml In Cyclohexane

81. Ncgc00255512-01

82. Cas-485-31-4

83. Db-051558

84. Ft-0603417

85. Binapacryl, Pestanal(r), Analytical Standard

86. C19022

87. Q3468507

88. (rs)-2-sec-butyl-4,6-dinitrophenyl 3-methylcrotonate

89. 2-(butan-2-yl)-4,6-dinitrophenyl 3-methylbut-2-enoate

90. 2-sec-butyl-4,6-dinitrophenyl 3-methylcrotonate (binapacryl)

91. 4,6-dinitro-2-sec-butylphenyl .beta.,.beta.-dimethylacrylate

92. 2-(1-methylpropyl)-4,6-dinitrophenyl .beta.,.beta.-dimethacrylate

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₈N₂O₆
Molecular Weight	322.31 g/mol
XLogP3	4.6
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	322.11648630 g/mol
Monoisotopic Mass	322.11648630 g/mol
Topological Polar Surface Area	118 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	489
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Absorption, Distribution and Excretion

BINAPACRYL WAS ABSORBED POORLY, IF AT ALL, THROUGH SKIN OF MICE AND RABBITS.

Menzie, C.M. Metabolism of Pesticides. U.S. Department of the Interior, Bureau of Sport Fisheries and Wildlife, Publication 127. Washington, DC: U.S. Government Printing Office, 1969., p. 170

After a single administration of binapacryl, both rats and rabbits excreted 7-17% in the urine within 48 hr. As late as the tenth day, 0.12% of the dose was detected in the urine of rats ... .

Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 470

4.2 Metabolism/Metabolites

WHEN ADMINISTERED ORALLY TO GUINEA PIGS, THIS COMPOUND GIVES RISE TO ... /2-SEC-BUTYL-4,6-DINITROPHENOL/ IN BLOOD.

Menzie, C.M. Metabolism of Pesticides. U.S. Department of the Interior, Bureau of Sport Fisheries and Wildlife, Publication 127. Washington, DC: U.S. Government Printing Office, 1969., p. 170

Following oral doses of binapacryl, the urine of both rabbits and rats contained oxidation products of the butyl side chain of dinoseb, including the acid. In addition, rat urine contained traces of free 6-aminophenol and the urine of rabbits contained a substantial amount of this compound and its glucuronide.

Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 470

4.3 Mechanism of Action

BASIC MECHANISM OF TOXICITY IS STIMULATION OF OXIDATIVE METABOLISM IN CELL MITOCHONDRIA, BY INTERFERENCE WITH NORMAL COUPLING OF CARBOHYDRATE OXIDN TO PHOSPHORYLATION (ADP TO ATP). INCR OXIDATIVE METABOLISM LEADS TO PYREXIA, TACHYCARDIA, & DEHYDRATION, & ULTIMATELY DEPLETES CARBOHYDRATE & FAT STORES. /NITROPHENOLIC COMPOUNDS/

Morgan, D.P. Recognition and Management of Pesticide Poisonings. EPA 540/9-80-005. Washington, DC: U.S. Government Printing Office, Jan. 1982., p. 23

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