Azamethiphos | CAS#35575-96-3 | insecticide

MedKoo Cat#: 461672 | Name: Azamethiphos

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Description:

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

Azamethiphos is an organothiophosphate insecticide. It is a veterinary drug used in Atlantic salmon fish farming to control parasites.

Chemical Structure

Azamethiphos

CAS#35575-96-3

Theoretical Analysis

MedKoo Cat#: 461672

Name: Azamethiphos

CAS#: 35575-96-3

Chemical Formula: C9H10ClN2O5PS

Exact Mass: 323.9737

Molecular Weight: 324.67

Elemental Analysis: C, 33.29; H, 3.10; Cl, 10.92; N, 8.63; O, 24.64; P, 9.54; S, 9.87

Price and Availability

Size	Price	Availability	Quantity
250mg	USD 250.00	2 Weeks
1g	USD 550.00	2 Weeks

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Related CAS #

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Synonym

Azamethiphos;

IUPAC/Chemical Name

S-((6-chloro-2-oxooxazolo[4,5-b]pyridin-3(2H)-yl)methyl) O,O-dimethyl phosphorothioate

InChi Key

VNKBTWQZTQIWDV-UHFFFAOYSA-N

InChi Code

InChI=1S/C9H10ClN2O5PS/c1-15-18(14,16-2)19-5-12-8-7(17-9(12)13)3-6(10)4-11-8/h3-4H,5H2,1-2H3

SMILES Code

O=P(OC)(SCN(C1=NC=C(Cl)C=C1O2)C2=O)OC

Appearance

Solid powder

Purity

>95% (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

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 324.67 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.

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

1: Kaur K, Helgesen KO, Bakke MJ, Horsberg TE. Mechanism behind Resistance against the Organophosphate Azamethiphos in Salmon Lice (Lepeophtheirus salmonis). PLoS One. 2015 Apr 20;10(4):e0124220. doi: 10.1371/journal.pone.0124220. eCollection 2015. PubMed PMID: 25893248; PubMed Central PMCID: PMC4403986. 2: Olsvik PA, Ørnsrud R, Lunestad BT, Steine N, Fredriksen BN. Transcriptional responses in Atlantic salmon (Salmo salar) exposed to deltamethrin, alone or in combination with azamethiphos. Comp Biochem Physiol C Toxicol Pharmacol. 2014 May;162:23-33. doi: 10.1016/j.cbpc.2014.03.005. Epub 2014 Mar 24. PubMed PMID: 24674905. 3: Couillard CM, Burridge LE. Sublethal exposure to azamethiphos causes neurotoxicity, altered energy allocation and high mortality during simulated live transport in American lobster. Ecotoxicol Environ Saf. 2015 May;115:291-9. doi: 10.1016/j.ecoenv.2014.11.016. Epub 2014 Dec 9. PubMed PMID: 25499691. 4: Marín SL, Ibarra R, Medina MH, Jansen PA. Sensitivity of Caligus rogercresseyi (Boxshall and Bravo 2000) to pyrethroids and azamethiphos measured using bioassay tests-A large scale spatial study. Prev Vet Med. 2015 Nov 1;122(1-2):33-41. doi: 10.1016/j.prevetmed.2015.09.017. Epub 2015 Oct 9. PubMed PMID: 26455388. 5: Dounia D, Andrea B, Lefort N, Van Geest JL. Repeated sublethal exposures to the sea lice pesticide Salmosan® (azamethiphos) on adult male lobsters (Homarus americanus) causes neuromuscular dysfunction, hypoxia, metabolic disturbances and mortality. Ecotoxicol Environ Saf. 2016 Dec;134P1:106-115. doi: 10.1016/j.ecoenv.2016.08.019. Epub 2016 Sep 2. PubMed PMID: 27591805. 6: Kaur K, Jansen PA, Aspehaug VT, Horsberg TE. Phe362Tyr in AChE: A Major Factor Responsible for Azamethiphos Resistance in Lepeophtheirus salmonis in Norway. PLoS One. 2016 Feb 16;11(2):e0149264. doi: 10.1371/journal.pone.0149264. eCollection 2016. PubMed PMID: 26882536; PubMed Central PMCID: PMC4755660. 7: Canty MN, Hagger JA, Moore RT, Cooper L, Galloway TS. Sublethal impact of short term exposure to the organophosphate pesticide azamethiphos in the marine mollusc Mytilus edulis. Mar Pollut Bull. 2007 Apr;54(4):396-402. Epub 2007 Jan 30. PubMed PMID: 17266995. 8: Burridge LE, Haya K, Waddy SL. Seasonal lethality of the organophosphate pesticide, azamethiphos to female American lobster (Homarus americanus). Ecotoxicol Environ Saf. 2005 Mar;60(3):277-81. PubMed PMID: 15590004. 9: Boltaña S, Chávez-Mardones J, Valenzuela-Muñoz V, Gallardo-Escárate C. Evidence for the Induction of Key Components of the NOTCH Signaling Pathway via Deltamethrin and Azamethiphos Treatment in the Sea Louse Caligus rogercresseyi. Int J Mol Sci. 2016 May 12;17(5). pii: E304. doi: 10.3390/ijms17050304. PubMed PMID: 27187362; PubMed Central PMCID: PMC4881433. 10: Saito K, Motoyama N, Dauterman WC. Effect of synergists on the oral and topical toxicity of azamethiphos to organophosphate-resistant houseflies (Diptera: Muscidae). J Econ Entomol. 1992 Aug;85(4):1041-5. PubMed PMID: 1517504. 11: Pretti C, Soldani G, Cognetti-Varriale AM, Monni G, Meucci V, Intorre L. Efficacy and safety of azamethiphos for the treatment of pseudodactylogyrosis in the European eel. J Vet Pharmacol Ther. 2002 Apr;25(2):155-7. PubMed PMID: 12000536. 12: Burridge LE, Haya K, Waddy SL. The effect of repeated exposure to azamethiphos on survival and spawning in the American lobster (Homarus americanus). Ecotoxicol Environ Saf. 2008 Mar;69(3):411-5. Epub 2007 Jun 25. PubMed PMID: 17590439. 13: Intorre L, Soldani G, Cognetti-Varriale AM, Monni G, Meucci V, Pretti C. Safety of azamethiphos in eel, seabass and trout. Pharmacol Res. 2004 Feb;49(2):171-6. PubMed PMID: 14643697. 14: Kocisová A, Para L. [Effectiveness of azamethiphos-based insecticides against the housefly (Musca domestica L.)]. Vet Med (Praha). 1995;40(1):17-22. Slovak. PubMed PMID: 7716864. 15: Núñez-Acuña G, Gallardo-Escárate C. Two novel male-associated peroxinectin genes are downregulated by exposure to delousing drugs in Caligus rogercresseyi. Gene. 2015 Feb 15;557(1):98-102. doi: 10.1016/j.gene.2014.12.006. Epub 2014 Dec 5. PubMed PMID: 25485718. 16: Burridge LE, Haya K, Zitko V, Waddy S. The lethality of Salmosan (Azamethiphos) to American lobster (Homarus americanus) larvae, postlarvae, and adults. Ecotoxicol Environ Saf. 1999 Jun;43(2):165-9. PubMed PMID: 10375419. 17: Zitko V. Alkylating potency of azamethiphos. Bull Environ Contam Toxicol. 2001 Mar;66(3):283-6. PubMed PMID: 11178640. 18: Pfenning AP, Roybal JE, Turnipseed SB, Gonzales SA, Hurlbut JA. Determination of residues of azamethiphos in salmon tissue by liquid chromatography with fluorescence detection. J AOAC Int. 1999 Sep-Oct;82(5):1224-8. PubMed PMID: 10513020. 19: O'Halloran J, Hogans WE. First use in North America of azamethiphos to treat Atlantic salmon for sea lice infestation: procedures and efficacy. Can Vet J. 1996 Oct;37(10):610-1. PubMed PMID: 8896875; PubMed Central PMCID: PMC1576483. 20: Saito K, Motoyama N, Dauterman WC. Studies on the resistance to various insecticides of a house fly strain (Diptera: Muscidae) selected with azamethiphos. J Econ Entomol. 1991 Dec;84(6):1635-7. PubMed PMID: 1787217.