Methiocarb
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MedKoo CAT#: 525615

CAS#: 2032-65-7

Description: Methiocarb is a carbamate pesticide which is used as a bird repellent, insecticide, acaricide and molluscicide. Methiocarb inhibits reversibly acetylcholinesterase activity resulting in a cholinergic stimulation making methiocarb a potent neurotoxin.

Chemical Structure

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Methiocarb
CAS# 2032-65-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 525615
Name: Methiocarb
CAS#: 2032-65-7
Chemical Formula: C11H15NO2S
Exact Mass: 225.08
Molecular Weight: 225.306
Elemental Analysis: C, 58.64; H, 6.71; N, 6.22; O, 14.20; S, 14.23

Price and Availability

Size Price Availability Quantity
50mg USD 250 2 Weeks
100mg USD 400 2 weeks
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Synonym: Mercaptodimethur; Mesurol; Methiocarb, BAY 37344; BAY-37344; BAY37344

IUPAC/Chemical Name: 3,5-dimethyl-4-(methylthio)phenyl methylcarbamate

InChi Key: YFBPRJGDJKVWAH-UHFFFAOYSA-N

InChi Code: InChI=1S/C11H15NO2S/c1-7-5-9(14-11(13)12-3)6-8(2)10(7)15-4/h5-6H,1-4H3,(H,12,13)

SMILES Code: O=C(OC1=CC(C)=C(SC)C(C)=C1)NC

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, not in water

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: Methiocarb is a carbamate pesticide.
In vitro activity: This study examined the potential of 8 antiCHE insecticides (4 carbamates and 4 organophosphates) to inhibit IL2-dependent proliferation of mouse CTLL2 cells. The order of potency for T cell inhibition was carbaryl = dichlorvos > methiocarb > carbofuran > paraoxon > mevinphos > aldicarb = monocrotophos. In view of the relatively high inhibitory potency of carbaryl (a carbamate with low cholinergic toxicity), 3 metabolites and 5 congeners of carbaryl were tested for potency to inhibit CTLL2 proliferation. Reference: Immunopharmacol Immunotoxicol. 1993 Mar-Jun;15(2-3):199-215. https://pubmed.ncbi.nlm.nih.gov/8349949/
In vivo activity: Therefore, the present study was aimed to evaluate the effect of acute MC exposure on lipid peroxidation, antioxidant defense systems, histological changes in Wistar rats and the protective effect of pretreatment with vitamin E and taurine. The rats administered with MC showed significant increase in the levels of malondialdehyde in the liver and kidney as an index of lipid peroxidation. Levels of glutathione and activities of superoxide dismutase, catalase and glutathione peroxidase were significantly increased, while activity of glutathione reductase remained unchanged in both the tissues after MC treatment. Reference: Toxicol Ind Health. 2013 Feb;29(1):60-71. https://pubmed.ncbi.nlm.nih.gov/22623520/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 20.0 88.77
DMSO 20.0 88.77
DMSO:PBS (pH 7.2) (1:1) 0.5 2.22
Ethanol 10.0 44.38

Preparing Stock Solutions

The following data is based on the product molecular weight 225.31 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. Casale GP, Vennerstrom JL, Bavari S, Wang TL. Inhibition of interleukin 2 driven proliferation of mouse CTLL2 cells, by selected carbamate and organophosphate insecticides and congeners of carbaryl. Immunopharmacol Immunotoxicol. 1993 Mar-Jun;15(2-3):199-215. doi: 10.3109/08923979309025994. PMID: 8349949. 2. Ozden S, Catalgol B, Gezginci-Oktayoglu S, Karatug A, Bolkent S, Alpertunga B. Acute effects of methiocarb on oxidative damage and the protective effects of vitamin E and taurine in the liver and kidney of Wistar rats. Toxicol Ind Health. 2013 Feb;29(1):60-71. doi: 10.1177/0748233712446719. Epub 2012 May 23. PMID: 22623520. 3. Han J, Park M, Kim JH, Kim A, Won M, Lee DR, Ko JJ, Yoon H, Sim SH, Lee K, Bae J. Increased expression of the testicular estrogen receptor alpha in adult mice exposed to low doses of methiocarb. J Appl Toxicol. 2009 Jul;29(5):446-51. doi: 10.1002/jat.1417. PMID: 19206145.
In vitro protocol: 1. Casale GP, Vennerstrom JL, Bavari S, Wang TL. Inhibition of interleukin 2 driven proliferation of mouse CTLL2 cells, by selected carbamate and organophosphate insecticides and congeners of carbaryl. Immunopharmacol Immunotoxicol. 1993 Mar-Jun;15(2-3):199-215. doi: 10.3109/08923979309025994. PMID: 8349949.
In vivo protocol: 1. Ozden S, Catalgol B, Gezginci-Oktayoglu S, Karatug A, Bolkent S, Alpertunga B. Acute effects of methiocarb on oxidative damage and the protective effects of vitamin E and taurine in the liver and kidney of Wistar rats. Toxicol Ind Health. 2013 Feb;29(1):60-71. doi: 10.1177/0748233712446719. Epub 2012 May 23. PMID: 22623520. 2. Han J, Park M, Kim JH, Kim A, Won M, Lee DR, Ko JJ, Yoon H, Sim SH, Lee K, Bae J. Increased expression of the testicular estrogen receptor alpha in adult mice exposed to low doses of methiocarb. J Appl Toxicol. 2009 Jul;29(5):446-51. doi: 10.1002/jat.1417. PMID: 19206145.

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1: Tange S, Fujimoto N, Uramaru N, Wong FF, Sugihara K, Ohta S, Kitamura S. In vitro metabolism of methiocarb and carbaryl in rats, and its effect on their estrogenic and antiandrogenic activities. Environ Toxicol Pharmacol. 2016 Jan;41:289-97. doi: 10.1016/j.etap.2015.08.014. Epub 2015 Aug 14. PubMed PMID: 26774076.
2: Qiang Z, Tian F, Liu W, Liu C. Degradation of methiocarb by monochloramine in water treatment: kinetics and pathways. Water Res. 2014 Mar 1;50:237-44. doi: 10.1016/j.watres.2013.12.011. Epub 2013 Dec 18. PubMed PMID: 24380738.
3: Plácido A, Paíga P, Lopes DH, Correia M, Delerue-Matos C. Determination of methiocarb and its degradation products, methiocarb sulfoxide and methiocarb sulfone, in bananas using QuEChERS extraction. J Agric Food Chem. 2013 Jan 16;61(2):325-31. doi: 10.1021/jf304027s. Epub 2013 Jan 3. PubMed PMID: 23252625.
4: Kaye BM, Elliott CR, Jalim SL. Methiocarb poisoning of a horse in Australia. Aust Vet J. 2012 Jun;90(6):221-4. doi: 10.1111/j.1751-0813.2012.00910.x. Epub 2012 Apr 9. PubMed PMID: 22632285.
5: Ozden S, Catalgol B, Gezginci-Oktayoglu S, Karatug A, Bolkent S, Alpertunga B. Acute effects of methiocarb on oxidative damage and the protective effects of vitamin E and taurine in the liver and kidney of Wistar rats. Toxicol Ind Health. 2013 Feb;29(1):60-71. doi: 10.1177/0748233712446719. Epub 2012 May 23. PubMed PMID: 22623520.
6: Ding XP, Tang DB, Li T, Wang SF, Zhou YY. A novel spectrofluorometric method for the determination of methiocarb using an amphiphilic p-sulfonatocalix[4]arene. Spectrochim Acta A Mol Biomol Spectrosc. 2011 Oct 15;81(1):44-7. doi: 10.1016/j.saa.2011.05.038. Epub 2011 May 23. PubMed PMID: 21737343.
7: Tian F, Qiang Z, Liu C, Zhang T, Dong B. Kinetics and mechanism for methiocarb degradation by chlorine dioxide in aqueous solution. Chemosphere. 2010 Apr;79(6):646-51. doi: 10.1016/j.chemosphere.2010.02.015. Epub 2010 Mar 1. PubMed PMID: 20189628.
8: Ozden S, Alpertunga B. Effects of methiocarb on lipid peroxidation and glutathione level in rat tissues. Drug Chem Toxicol. 2010;33(1):50-4. doi: 10.3109/01480540903130708. PubMed PMID: 19827908.
9: Blazková M, Micková-Holubová B, Rauch P, Fukal L. Immunochromatographic colloidal carbon-based assay for detection of methiocarb in surface water. Biosens Bioelectron. 2009 Dec 15;25(4):753-8. doi: 10.1016/j.bios.2009.08.023. Epub 2009 Aug 22. PubMed PMID: 19765968.
10: Ozden S, Catalgol B, Gezginci-Oktayoglu S, Arda-Pirincci P, Bolkent S, Alpertunga B. Methiocarb-induced oxidative damage following subacute exposure and the protective effects of vitamin E and taurine in rats. Food Chem Toxicol. 2009 Jul;47(7):1676-84. doi: 10.1016/j.fct.2009.04.018. Epub 2009 Apr 24. PubMed PMID: 19394395.
11: Han J, Park M, Kim JH, Kim A, Won M, Lee DR, Ko JJ, Yoon H, Sim SH, Lee K, Bae J. Increased expression of the testicular estrogen receptor alpha in adult mice exposed to low doses of methiocarb. J Appl Toxicol. 2009 Jul;29(5):446-51. doi: 10.1002/jat.1417. PubMed PMID: 19206145.
12: Altinok I, Capkin E. Histopathology of rainbow trout exposed to sublethal concentrations of methiocarb or endosulfan. Toxicol Pathol. 2007 Apr;35(3):405-10. PubMed PMID: 17455089.
13: Jiménez JJ, Bernal JL, del Nozal MJ, Toribio L, Bernal J. Use of SPE-GC/EIMS for residue analysis in wine elaborated from musts spiked with formulations of chlorpyriphos-methyl, methiocarb, dicofol, and cyproconazol. J Sep Sci. 2007 Mar;30(4):547-56. PubMed PMID: 17444223.
14: Padilla S, Marshall RS, Hunter DL, Lowit A. Time course of cholinesterase inhibition in adult rats treated acutely with carbaryl, carbofuran, formetanate, methomyl, methiocarb, oxamyl or propoxur. Toxicol Appl Pharmacol. 2007 Mar;219(2-3):202-9. Epub 2006 Nov 15. PubMed PMID: 17197007.
15: Maymó AC, Cervera A, Dolores Garcerá M, Bielza P, Martínez-Pardo R. Relationship between esterase activity and acrinathrin and methiocarb resistance in field populations of western flower thrips, Frankliniella occidentalis. Pest Manag Sci. 2006 Dec;62(12):1129-37. PubMed PMID: 16929461.
16: Altinok I, Capkin E, Karahan S, Boran M. Effects of water quality and fish size on toxicity of methiocarb, a carbamate pesticide, to rainbow trout. Environ Toxicol Pharmacol. 2006 Jul;22(1):20-6. doi: 10.1016/j.etap.2005.11.002. Epub 2006 Jan 18. PubMed PMID: 21783681.
17: Nielsen JB, Nielsen F. Topical use of tea tree oil reduces the dermal absorption of benzoic acid and methiocarb. Arch Dermatol Res. 2006 Mar;297(9):395-402. Epub 2005 Nov 29. PubMed PMID: 16315066.
18: Wilson C, Strimple P, Wilson S, Albano J. Nontarget deposition of methiocarb applied to a foliage plant staging area. Bull Environ Contam Toxicol. 2005 Mar;74(3):509-17. PubMed PMID: 15903185.
19: Hofmeister MV, Bonefeld-Jørgensen EC. Effects of the pesticides prochloraz and methiocarb on human estrogen receptor alpha and beta mRNA levels analyzed by on-line RT-PCR. Toxicol In Vitro. 2004 Aug;18(4):427-33. PubMed PMID: 15130599.
20: Péry AR, Mons R, Ducrot V, Garric J. Effects of methiocarb on Chironomus riparius survival and growth with and without tube-building. Bull Environ Contam Toxicol. 2004 Feb;72(2):358-64. PubMed PMID: 15106773.