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    Binapacryl

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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

    2D Structure

    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 Weight 322.31 g/mol
    Molecular Formula C15H18N2O6
    XLogP34.6
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count5
    Exact Mass322.11648630 g/mol
    Monoisotopic Mass322.11648630 g/mol
    Topological Polar Surface Area118 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity489
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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