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Chemistry

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Also known as: 60-51-5, Phosphamide, Rogor, Phosphamid, Lurgo, Aadimethoal
Molecular Formula
C5H12NO3PS2
Molecular Weight
229.3  g/mol
InChI Key
MCWXGJITAZMZEV-UHFFFAOYSA-N
FDA UNII
W6U08B045O

Dimethoate
An organothiophosphorus cholinesterase inhibitor that is used as a systemic and contact insecticide.
1 2D Structure

Dimethoate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-dimethoxyphosphinothioylsulfanyl-N-methylacetamide
2.1.2 InChI
InChI=1S/C5H12NO3PS2/c1-6-5(7)4-12-10(11,8-2)9-3/h4H2,1-3H3,(H,6,7)
2.1.3 InChI Key
MCWXGJITAZMZEV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CNC(=O)CSP(=S)(OC)OC
2.2 Other Identifiers
2.2.1 UNII
W6U08B045O
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bi 58

2. Bi-58

3. Bi58

4. Phosphamide

5. Rogor

2.3.2 Depositor-Supplied Synonyms

1. 60-51-5

2. Phosphamide

3. Rogor

4. Phosphamid

5. Lurgo

6. Aadimethoal

7. Fosfamid

8. Fosfotox

9. Perfecthion

10. Perfekthion

11. Rebelate

12. Sinoratox

13. Sistemin

14. Systoate

15. Daphene

16. Dimeton

17. Dimevur

18. Racusan

19. Roxion

20. Cygon

21. Tara

22. Fosfatox R

23. Fosfotox R

24. Cygon Insecticide

25. De-fend

26. Fostion Mm

27. Rogor L

28. Rogor P

29. Cygon 4e

30. Fosfotox R 35

31. Cygon 2-e

32. Rogor 40

33. Cygon 400

34. Tara 909

35. American Cyanamid 12880

36. 8014 Bis Hc

37. Pei 75

38. 2-dimethoxyphosphinothioylthio-n-methylacetamide

39. Bi 58

40. 2-dimethoxyphosphinothioylsulfanyl-n-methylacetamide

41. Cl 12880

42. O,o-dimethyl S-(2-(methylamino)-2-oxoethyl) Phosphorodithioate

43. O,o-dimethyl S-methylcarbamoylmethyl Phosphorodithioate

44. L-395

45. O,o-dimethyl S-[2-(methylamino)-2-oxoethyl] Dithiophosphate

46. Phosphorodithioic Acid, O,o-dimethyl S-(2-(methylamino)-2-oxoethyl) Ester

47. S-methylcarbamoylmethyl O,o-dimethyl Phosphorodithioate

48. O,o-dimethyl S-(n-methylcarbamoylmethyl) Dithiophosphate

49. Phosphorodithioic Acid, O,o-dimethyl Ester, S-ester With 2-mercapto-n-methylacetamide

50. O,o-dimethyl S-(n-methylcarbamoylmethyl) Phosphorodithioate

51. Chebi:34714

52. W6u08b045o

53. Fip

54. Cekuthoate

55. Devigon

56. Dimetate

57. Dimethogen

58. Ferkethion

59. Rogodan

60. Sevigor

61. Trimetion

62. O,o-dimethyl S-[2-(methylamino)-2-oxoethyl] Phosphorodithioate

63. Salut

64. Solut

65. Dsstox_cid_479

66. Fortion Nm

67. Phosphorodithioic Acid, O,o-dimethyl S-[2-(methylamino)-2-oxoethyl] Ester

68. Phosphorodithioic Acid, O,o-dimethyl S-[2-(methylamino)-2-oxoethyl]ester

69. Roxion Ua

70. Dsstox_rid_75615

71. Dsstox_gsid_20479

72. Fosfamid (ussr)

73. Dimethoaat [dutch]

74. Dimethoat [german]

75. Dimethoate 30 Ec

76. Demos-l40

77. Rogor 20l

78. Dimate 267

79. Dimethoat Tech 95%

80. Caswell No. 358

81. Dimethoaat

82. Dimethoat

83. Bi-58

84. Rcra Waste Number P044

85. Cas-60-51-5

86. Ditimur 40; Ent 24650; Experimental Insecticide 12880; Fip; Fosfatox R; Fosfotox

87. Ccris 245

88. Dimethoate [ansi:bsi:iso]

89. Bi 58 Ec

90. Oms 94

91. Hsdb 1586

92. Experimental Insecticide 12,880

93. Nci-c00135

94. Einecs 200-480-3

95. Rcra Waste No. P044

96. Ent 24,650

97. Epa Pesticide Chemical Code 035001

98. Brn 1785339

99. Ac-12880

100. Ac-18682

101. Ei-12880

102. Turbair

103. Unii-w6u08b045o

104. Ai3-24650

105. O,o-dimethyl Methylcarbamoylmethyl Phosphorodithioate

106. O,o-dimethyl S-((methylcarbamoyl)methyl)phosphorodithioate

107. Rogor 20 L

108. Spectrum_001793

109. N-monomethylamide Of O,o-dimethyldithiophosphorylacetic Acid

110. O,o-dimethyl S-(n-methylcarbamylmethyl) Thiothionophosphate

111. O,o-dimethyl-s-(2-oxo-3-aza-butyl)-dithiophosphat [german]

112. Dimethoate [mi]

113. Specplus_000384

114. O,o-dimethyl-dithiophosphorylessigsaeure Monomethylamid [german]

115. O,o-dimethyl-s-(n-monomethyl)-carbamyl Methyl Dithiophosphate

116. O,o-dimethyldithiophosphorylacetic Acid, N-monomethylamide Salt

117. O,o-dimetil-s-(n-metil-carbamoil-metil)-ditiofosfato [italian]

118. Dimethoate [iso]

119. Acetic Acid, O,o-dimethyldithiophosphoryl-, N-monomethylamide Salt

120. O,o-dimethyl-s-(n-methyl-carbamoyl)-methyl-dithiofosfaat [dutch]

121. Spectrum2_001861

122. Spectrum3_000812

123. Spectrum4_000652

124. Spectrum5_001934

125. Dimethoate [hsdb]

126. Dithiophosphate De O,o-dimethyle Et De S(-n-methylcarbamoyl-methyle) [french]

127. Dimethoate [mart.]

128. Phosphorodithioic Acid O,o-dimethyl Ester, Ester With 2-mercapto-n-methylacetamide

129. Schembl18159

130. Bspbio_002303

131. Kbiogr_001023

132. Kbioss_002286

133. Spectrum330020

134. Mls002207196

135. Bidd:er0567

136. Dimercaptan Triethylene Glycol

137. Divk1c_006480

138. O,o-dimethyl-s-(2-oxo-3-aza-butyl)-dithiophosphat

139. Spbio_001702

140. Dimethoate, Analytical Standard

141. O,o-dimethyl-dithiophosphorylessigsaeure Monomethylamid

142. O,o-dimetil-s-(n-metil-carbamoil-metil)-ditiofosfato

143. Chembl1569524

144. Dtxsid7020479

145. Schembl20525536

146. Experimental Insecticide 12880

147. Kbio1_001424

148. Kbio2_002284

149. Kbio2_004852

150. Kbio2_007420

151. Kbio3_001803

152. Mcwxgjitazmzev-uhfffaoysa-

153. Dimethoate-d6(o,o-dimethyl-d6)

154. O,o-dimethyl-s-(n-methyl-carbamoyl)-methyl-dithiofosfaat

155. O,o-dimethyl-s-(n-methyl-carbamoyl-methyl)-dithiophosphat

156. Hy-b1946

157. Tox21_202246

158. Tox21_301161

159. Ccg-39399

160. Dimethoate 100 Microg/ml In Hexane

161. Dithiophosphate De O,o-dimethyle Et De S(-n-methylcarbamoyl-methyle)

162. Ent-24650

163. Mfcd00053676

164. O,o-dimethyl-s-(n-methyl-carbamoyl-methyl)-dithiophosphat [german]

165. Dimethoate 100 Microg/ml In Acetone

166. Akos015960721

167. Dimethoate 100 Microg/ml In Methanol

168. O,o-dimethyl Phosphorodithioate S-ester With 2-mercapto-n-methylacetamide

169. Dimethoate 1000 Microg/ml In Acetone

170. Dimethoate 10 Microg/ml In Cyclohexane

171. Dimethoate 1000 Microg/ml In Methanol

172. Ncgc00094518-01

173. Ncgc00094518-02

174. Ncgc00094518-03

175. Ncgc00094518-04

176. Ncgc00094518-05

177. Ncgc00094518-06

178. Ncgc00094518-07

179. Ncgc00094518-08

180. Ncgc00255059-01

181. Ncgc00259795-01

182. As-16078

183. Dimethoate 100 Microg/ml In Acetonitrile

184. L395

185. Smr000777935

186. Db-053635

187. Cs-0014051

188. Ft-0603252

189. Ft-0667209

190. L 395

191. Dimethoate, Pestanal(r), Analytical Standard

192. 053d676

193. Q421371

194. Brd-k94763113-001-02-5

195. O,o-dimethyl S-[2-(methylamino)-2-oxoethyl] Dithiophosphate #

196. O,o-dimethyl S-[2-(methylamino)-2-oxoethyl]phosphorodithioate

197. O,o-dimethyl S-2-(methylamino)-2-oxoethyl Phosphorodithioate

198. (z)-2-{[dimethoxy(sulfanylidene)-

199. E?-phosphanyl]sulfanyl}-n-methylethanimidic Acid

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 229.3 g/mol
Molecular Formula C5H12NO3PS2
XLogP30.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Exact Mass228.99962259 g/mol
Monoisotopic Mass228.99962259 g/mol
Topological Polar Surface Area105 Ų
Heavy Atom Count12
Formal Charge0
Complexity191
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Medication (Vet): Also used experimentally in many species by many routes (spray, oral, sc, im, pour on, etc), and has shown particular effectiveness against grubs in cattle and reindeer (10 and 30 mg/kg upper safe limits, respectively) and oestrus ovis in sheep (25 mg/kg sc- avoid use in hot or tired animals). Older materials may be more toxic to animals.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 179


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Cholinesterase Inhibitors

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)


Insecticides

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)


5.2 Absorption, Distribution and Excretion

Qualitatively, metabolism of dimethoate in mammals is essentially identical to that occurring in insects. There are... quantitative differences. In general, dimethoate, is much more rapidly degraded in mammals and eliminated via urine. For example, 87-90% of oral dose given cattle was found in urine after 24 hr, mainly as hydrolysis products.

White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New York: Marcel Dekker, Inc., 1971., p. 168


...After ingestion of dimethoate, rats eliminate 60% of dose in 24 hr in urine and expired air.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 282


... Dimethoate rapidly penetrated isolated sections of /mouse/ small intestine, colon, and rectum, with the highest rates of penetration occurring in the colon and rectum. The age of the mice had no significant effects on the extent of penetration. /Initial dose not specified/

Shah PV, Guthrie FE; Toxicol Appl Pharmacol 25: 621-4 (1973) as cited in USEPA/ECAO; Health and Environmental Effects Profile for Dimethoate (Final Draft) p.9 (1984) ECAO-CIN-PO81


... Following aerial spraying with 38% dimethoate animal tissues contained higher concentrations of dimethoate than did soil, water or plants. ... The tissue containing the highest concentrations were brain and intially, lung. ...

Fedrorenko AP et al; Vestn Zool 4: 89-92 (1981) as cited in USEPA/ECAO; Health Effects Profile for Dimethoate (Final Draft) p.9-10 (1984) ECAO-CIN-PO81


For more Absorption, Distribution and Excretion (Complete) data for DIMETHOATE (23 total), please visit the HSDB record page.


5.3 Metabolism/Metabolites

... Detoxification pathway ... involves the hydrolysis of carboxyester or carboxyamide linkages in some insecticides by tissue or plasma carboxylesterases (sometimes called aliesterase). Malathion and dimethoate are examples.

Doull, J., C.D.Klassen, and M.D. Amdur (eds.). Casarett and Doull's Toxicology. 3rd ed., New York: Macmillan Co., Inc., 1986., p. 534


Rabbit and rat liver microsomes converted dimethoate to oxygen analog and des-N-methyl derivatives.

Menzie, C. M. Metabolism of Pesticides, An Update. U.S. Department of the Interior, Fish, Wild-life Service, Special Scientific Report - Wildlife No. 184, Washington, DC: U.S. Government Printing Office, l974., p. 166


After dimethoate was administered to rats, the following compounds were found in urine: 1. dimethoate, 2. dimethoxon, 3. dimethoate carboxylic acid, 4. dimethylphosphorodithioate, 5. dimethyl phosphorothioate, 6. dimethylphosphate, 7. monomethylphosphate, 8. phosphorothioate, 9. formate, and 10. N-methyl 2-glucuronate acetamide.

Menzie, C. M. Metabolism of Pesticides, An Update. U.S. Department of the Interior, Fish, Wild-life Service, Special Scientific Report - Wildlife No. 184, Washington, DC: U.S. Government Printing Office, l974., p. 166


Oxidative desulfuration of dimethoate to give O-analog took place rapidly in rabbits and rats. Both dimethoate and O-analog underwent subsequent oxidative N-dealkylation coupled with formation of N-hydroxymethyl intermediates.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 287


For more Metabolism/Metabolites (Complete) data for DIMETHOATE (28 total), please visit the HSDB record page.


Dimethoate has known human metabolites that include Omethoate.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.4 Mechanism of Action

Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase (AChE). ... The inactivation of cholinesterase by cholinesterase inhibitor pesticides allows the accumulation of large amounts of acetylcholine, with resultant widespread effects that may be ... separated into 4 categories: (1) Potentiation of postganglionic parasympathetic activity. ... (2) Persistent depolarization of skeletal muscle ... (3) Initial stimulation following depression of cells of central nervous system ... (4) Variable ganglionic stimulation or blockade ... /Cholinesterase inhibitor pesticides/

Dreisbach, R.H. Handbook of Poisoning. 12th ed. Norwalk, CT: Appleton and Lange, 1987., p. 113


They act principally by inhibition of acetyl cholinesterase (AChE) at the cholinergic synapses. /organophosphorus insecticides/

WHO; Environ Health Criteria Number 90: Dimethoate p.50 (1989)


The signs of poisoning due to organophosphorus cmpd are those due to accumulation of acetylcholine & hence overstimulation of parasympathetic nervous system. It is usual to divide them under 3 headings: muscarinic, nicotinic & central. Muscarinic signs ... consist of hypersalivation, lacrimation, sweating & nasal discharge. Miosis, dyspnea, vomiting, diarrhea & frequency of urination ... Nicotinic effects consist of fasciculation of muscles, weakness & paralysis. Central nervous system effects include nervousness, apprehension, ataxia, convulsions & coma. Death is due to resp failure, or sometimes cardiac arrest. There is little difference between signs produced by different organophosphorus compounds, but route of absorption may influence one system more than another. /Organophosphorus cmpd/

Clarke, M. L., D. G. Harvey and D. J. Humphreys. Veterinary Toxicology. 2nd ed. London: Bailliere Tindall, 1981., p. 153


Toxicants of this class phosphorylate almost irreversibly varying amt of acetylcholinesterase enzyme of tissues, allowing accum of acetylcholine at cholinergic neuro-effector junctions (muscarinic effects), & at skeletal muscle myoneural junctions & in autonomic ganglia (nicotinic effects). /Organophosphate pesticides/

Morgan, D. P. Recognition and Management of Pesticide Poisonings. 2nd ed. EPA 540/9-76-011, Washington, DC: U.S. Government Printing Office, Aug. 1976., p. 4


For more Mechanism of Action (Complete) data for DIMETHOATE (6 total), please visit the HSDB record page.


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