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MedKoo Cat#: 551053 | Name: Monocrotophos
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Monocrotophos is an organophosphate insecticide that blocks monoamine oxidase and acetylcholinesterase.

Chemical Structure

Monocrotophos
Monocrotophos
CAS#6923-22-4

Theoretical Analysis

MedKoo Cat#: 551053

Name: Monocrotophos

CAS#: 6923-22-4

Chemical Formula: C7H14NO5P

Exact Mass: 223.0610

Molecular Weight: 223.16

Elemental Analysis: C, 37.67; H, 6.32; N, 6.28; O, 35.85; P, 13.88

Price and Availability

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100mg USD 185.00
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Synonym
IUPAC/Chemical Name
(E)-dimethyl (4-(methylamino)-4-oxobut-2-en-2-yl) phosphate
InChi Key
KRTSDMXIXPKRQR-AATRIKPKSA-N
InChi Code
InChI=1S/C7H14NO5P/c1-6(5-7(9)8-2)13-14(10,11-3)12-4/h5H,1-4H3,(H,8,9)/b6-5+
SMILES Code
O=P(OC)(OC)O/C(C)=C/C(NC)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Monocrotophos is an organophosphate insecticide that blocks monoamine oxidase and acetylcholinesterase.
In vitro activity:
The conditioned medium (CM) of differentiated PC12 cells comprising of their secretome restored the cell viability, oxidative stress and apoptotic cell death in MCP (monocrotophos)-challenged human mesenchymal stem cells and SHSY-5Y, a human neuroblastoma cell line. Besides that, the increased mitochondrial fission in MCP-exposed cells was balanced with increased fusion in the presence of CM facilitated by AMPK/SIRT1/PGC-1α signaling cascade. Reference: Neuromolecular Med. 2018 Jun;20(2):233-251. https://pubmed.ncbi.nlm.nih.gov/29603067/
In vivo activity:
Male Wistar rats were given NAC (N-acetylcysteine) (200 mg/kg b.wt), MCP (monocrotophos) (0.9 mg/kg b.wt) and NAC together with MCP, intragastrically for 28 consecutive days. Mitochondrial complexes activities were evaluated using biochemical analysis. Exposure of MCP (0.9 mg/kg b.wt, intragastrically, 28 d) decreased mitochondrial complexes activities and gene expression of complexes subunits. Reference: Toxicol Mech Methods. 2022 Nov;32(9):686-694. https://pubmed.ncbi.nlm.nih.gov/35403558/

Preparing Stock Solutions

The following data is based on the product molecular weight 223.16 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Srivastava A, Singh S, Rajpurohit CS, Srivastava P, Pandey A, Kumar D, Khanna VK, Pant AB. Secretome of Differentiated PC12 Cells Restores the Monocrotophos-Induced Damages in Human Mesenchymal Stem Cells and SHSY-5Y Cells: Role of Autophagy and Mitochondrial Dynamics. Neuromolecular Med. 2018 Jun;20(2):233-251. doi: 10.1007/s12017-018-8487-9. Epub 2018 Mar 30. PMID: 29603067. 2. Jahan S, Kumar D, Singh S, Kumar V, Srivastava A, Pandey A, Rajpurohit CS, Khanna VK, Pant AB. Resveratrol Prevents the Cellular Damages Induced by Monocrotophos via PI3K Signaling Pathway in Human Cord Blood Mesenchymal Stem Cells. Mol Neurobiol. 2018 Nov;55(11):8278-8292. doi: 10.1007/s12035-018-0986-z. Epub 2018 Mar 10. PMID: 29526017. 3. Singh J, Phogat A, Kumar V, Malik V. N-acetylcysteine ameliorates monocrotophos exposure-induced mitochondrial dysfunctions in rat liver. Toxicol Mech Methods. 2022 Nov;32(9):686-694. doi: 10.1080/15376516.2022.2064258. Epub 2022 Apr 21. PMID: 35403558. 4. Ali SJ. Monocrotophos, an organophosphorus insecticide, induces cortical and trabecular bone loss in Swiss albino mice. Chem Biol Interact. 2020 Sep 25;329:109112. doi: 10.1016/j.cbi.2020.109112. Epub 2020 Apr 29. PMID: 32360284.
In vitro protocol:
1. Srivastava A, Singh S, Rajpurohit CS, Srivastava P, Pandey A, Kumar D, Khanna VK, Pant AB. Secretome of Differentiated PC12 Cells Restores the Monocrotophos-Induced Damages in Human Mesenchymal Stem Cells and SHSY-5Y Cells: Role of Autophagy and Mitochondrial Dynamics. Neuromolecular Med. 2018 Jun;20(2):233-251. doi: 10.1007/s12017-018-8487-9. Epub 2018 Mar 30. PMID: 29603067. 2. Jahan S, Kumar D, Singh S, Kumar V, Srivastava A, Pandey A, Rajpurohit CS, Khanna VK, Pant AB. Resveratrol Prevents the Cellular Damages Induced by Monocrotophos via PI3K Signaling Pathway in Human Cord Blood Mesenchymal Stem Cells. Mol Neurobiol. 2018 Nov;55(11):8278-8292. doi: 10.1007/s12035-018-0986-z. Epub 2018 Mar 10. PMID: 29526017.
In vivo protocol:
1. Srivastava A, Singh S, Rajpurohit CS, Srivastava P, Pandey A, Kumar D, Khanna VK, Pant AB. Secretome of Differentiated PC12 Cells Restores the Monocrotophos-Induced Damages in Human Mesenchymal Stem Cells and SHSY-5Y Cells: Role of Autophagy and Mitochondrial Dynamics. Neuromolecular Med. 2018 Jun;20(2):233-251. doi: 10.1007/s12017-018-8487-9. Epub 2018 Mar 30. PMID: 29603067. 2. Jahan S, Kumar D, Singh S, Kumar V, Srivastava A, Pandey A, Rajpurohit CS, Khanna VK, Pant AB. Resveratrol Prevents the Cellular Damages Induced by Monocrotophos via PI3K Signaling Pathway in Human Cord Blood Mesenchymal Stem Cells. Mol Neurobiol. 2018 Nov;55(11):8278-8292. doi: 10.1007/s12035-018-0986-z. Epub 2018 Mar 10. PMID: 29526017.
1: Sun L, Liu H, Gao X, Chen W, Huang K, Zhang S. Isolation of monocrotophos-degrading strain Sphingobiumsp. YW16 and cloning of its TnopdA. Environ Sci Pollut Res Int. 2017 Dec 4. doi: 10.1007/s11356-017-0718-3. [Epub ahead of print] PubMed PMID: 29204940. 2: Paz-Trejo C, Gómez-Arroyo S. Genotoxic evaluation of common commercial pesticides in human peripheral blood lymphocytes. Toxicol Ind Health. 2017 Dec;33(12):938-945. doi: 10.1177/0748233717736121. Epub 2017 Nov 14. PubMed PMID: 29137571. 3: Zhang S, Liu X, Qin J, Yang M, Zhao H, Wang Y, Guo W, Ma Z, Kong W. Rapid gas chromatography with flame photometric detection of multiple organophosphorus pesticides in Salvia miltiorrhizae after ultrasonication assisted one-step extraction. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Nov 15;1068-1069:233-238. doi: 10.1016/j.jchromb.2017.10.025. Epub 2017 Oct 14. PubMed PMID: 29107223. 4: Thakur S, Dhiman M, Mantha AK. APE1 modulates cellular responses to organophosphate pesticide-induced oxidative damage in non-small cell lung carcinoma A549 cells. Mol Cell Biochem. 2017 Sep 8. doi: 10.1007/s11010-017-3186-7. [Epub ahead of print] PubMed PMID: 28887667. 5: Hou YX, Liu SW, Wang LW, Wu SH. Physiopathology of multiple organ dysfunctions in severely monocrotophos-poisoned rabbits. Chem Biol Interact. 2017 Dec 25;278:9-14. doi: 10.1016/j.cbi.2017.08.016. Epub 2017 Aug 31. PubMed PMID: 28864276. 6: Sarkar B, Dhiman M, Mittal S, Mantha AK. Curcumin revitalizes Amyloid beta (25-35)-induced and organophosphate pesticides pestered neurotoxicity in SH-SY5Y and IMR-32 cells via activation of APE1 and Nrf2. Metab Brain Dis. 2017 Dec;32(6):2045-2061. doi: 10.1007/s11011-017-0093-2. Epub 2017 Aug 31. PubMed PMID: 28861684. 7: Jallow MFA, Awadh DG, Albaho MS, Devi VY, Ahmad N. Monitoring of Pesticide Residues in Commonly Used Fruits and Vegetables in Kuwait. Int J Environ Res Public Health. 2017 Jul 25;14(8). pii: E833. doi: 10.3390/ijerph14080833. PubMed PMID: 28757570; PubMed Central PMCID: PMC5580537. 8: Boulanouar S, Combès A, Mezzache S, Pichon V. Synthesis and application of molecularly imprinted polymers for the selective extraction of organophosphorus pesticides from vegetable oils. J Chromatogr A. 2017 Sep 1;1513:59-68. doi: 10.1016/j.chroma.2017.07.067. Epub 2017 Jul 20. PubMed PMID: 28755904. 9: Turkdogan KA, Duman A, Avcil M, Akoz A, Canakcı SE, Kantekin B. Treatment methods following suicidal self-administration of IV organophosphate: What can additional lipid administration change? Am J Emerg Med. 2017 Sep;35(9):1388.e3-1388.e5. doi: 10.1016/j.ajem.2017.06.058. Epub 2017 Jul 8. PubMed PMID: 28711273. 10: Zhang X, Xu L, Tian H, Wang C, Wang W, Ru S. Monocrotophos, an organophosphorus insecticide, disrupts the expression of HpNetrin and its receptor neogenin during early development in the sea urchin (Hemicentrotus pulcherrimus). Neurotoxicology. 2017 Sep;62:130-137. doi: 10.1016/j.neuro.2017.06.010. Epub 2017 Jun 20. PubMed PMID: 28645554. 11: Vasantha-Srinivasan P, Senthil-Nathan S, Ponsankar A, Thanigaivel A, Chellappandian M, Edwin ES, Selin-Rani S, Kalaivani K, Hunter WB, Duraipandiyan V, Al-Dhabi NA. Acute toxicity of chemical pesticides and plant-derived essential oil on the behavior and development of earthworms, Eudrilus eugeniae (Kinberg) and Eisenia fetida (Savigny). Environ Sci Pollut Res Int. 2017 Jun 17. doi: 10.1007/s11356-017-9236-6. [Epub ahead of print] PubMed PMID: 28624937. 12: Tian H, Sun Y, Wang H, Bing X, Wang W, Ru S. Monocrotophos pesticide affects synthesis and conversion of sex steroids through multiple targets in male goldfish (Carassius auratus). Sci Rep. 2017 May 23;7(1):2306. doi: 10.1038/s41598-017-01935-6. PubMed PMID: 28536437; PubMed Central PMCID: PMC5442159. 13: Zhang X, Li S, Wang C, Tian H, Wang W, Ru S. Effects of monocrotophos pesticide on cholinergic and dopaminergic neurotransmitter systems during early development in the sea urchin Hemicentrotus pulcherrimus. Toxicol Appl Pharmacol. 2017 Aug 1;328:46-53. doi: 10.1016/j.taap.2017.05.003. Epub 2017 May 4. PubMed PMID: 28479505. 14: Shah PC, Kumar VR, Dastager SG, Khire JM. Phytase production by Aspergillus niger NCIM 563 for a novel application to degrade organophosphorus pesticides. AMB Express. 2017 Dec;7(1):66. doi: 10.1186/s13568-017-0370-9. Epub 2017 Mar 21. PubMed PMID: 28321795; PubMed Central PMCID: PMC5359262. 15: Hasan F, Ansari MS. Lethal and Sublethal Effects of Insecticides on the Biological Attributes of Zygogramma bicolorata Pallister (Coleoptera: Chrysomelidae): a Biocontrol Agent of Parthenium hysterophorus L. Neotrop Entomol. 2017 Oct;46(5):473-486. doi: 10.1007/s13744-017-0485-3. Epub 2017 Jan 31. PubMed PMID: 28144909. 16: Naveen NC, Chaubey R, Kumar D, Rebijith KB, Rajagopal R, Subrahmanyam B, Subramanian S. Insecticide resistance status in the whitefly, Bemisia tabaci genetic groups Asia-I, Asia-II-1 and Asia-II-7 on the Indian subcontinent. Sci Rep. 2017 Jan 18;7:40634. doi: 10.1038/srep40634. PubMed PMID: 28098188; PubMed Central PMCID: PMC5241821. 17: Salim C, Rajini PS. Glucose-rich diet aggravates monocrotophos-induced dopaminergic neuronal dysfunction in Caenorhabditis elegans. J Appl Toxicol. 2017 Jun;37(6):772-780. doi: 10.1002/jat.3426. Epub 2016 Dec 20. PubMed PMID: 27995639. 18: Arora S, Balotra S, Pandey G, Kumar A. Binary combinations of organophosphorus and synthetic pyrethroids are more potent acetylcholinesterase inhibitors than organophosphorus and carbamate mixtures: An in vitro assessment. Toxicol Lett. 2017 Feb 15;268:8-16. doi: 10.1016/j.toxlet.2016.12.009. Epub 2016 Dec 14. PubMed PMID: 27988393. 19: Nagaraju R, Rajini PS. Adaptive response of rat pancreatic β-cells to insulin resistance induced by monocrotophos: Biochemical evidence. Pestic Biochem Physiol. 2016 Nov;134:39-48. doi: 10.1016/j.pestbp.2016.04.009. Epub 2016 Apr 30. PubMed PMID: 27914538. 20: Narra MR, Rajender K, Reddy RR, Murty US, Begum G. Insecticides induced stress response and recuperation in fish: Biomarkers in blood and tissues related to oxidative damage. Chemosphere. 2017 Feb;168:350-357. doi: 10.1016/j.chemosphere.2016.10.066. Epub 2016 Oct 27. PubMed PMID: 27810534.

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