An internal standard for the quantification of imidacloprid
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Unlabeled Version(s)
24130Imidacloprid
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Imidacloprid-d4

Item No. 39549

Technical Information
Formal Name
1-[(6-chloro-3-pyridinyl)methyl]-4,5-dihydro-4,5-d2-N-nitro-1H-imidazol-4,5-d2-2-amine
CAS Number
1015855-75-0
Molecular Formula
C9H6ClD4N5O2
Formula Weight
Purity
≥99% deuterated forms (d1-d4)
Formulation
A solid
DMSO: slightly solubleMethanol: slightly soluble
SMILES
ClC1=NC=C(CN2C(N[N+]([O-])=O)=NC([2H])([2H])C2([2H])[2H])C=C1
InChi Code
InChI=1S/C9H10ClN5O2/c10-8-2-1-7(5-12-8)6-14-4-3-11-9(14)13-15(16)17/h1-2,5H,3-4,6H2,(H,11,13)/i3D2,4D2
InChi Key
YWTYJOPNNQFBPC-KHORGVISSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Imidacloprid-d4 is intended for use as an internal standard for the quantification of imidacloprid (Item No. 24130) by GC- or LC-MS. Imidacloprid is a broad-spectrum neonicotinoid insecticide that is effective against sucking and biting insects and insects of the Coleopteran and Lepidoptera orders.1,2 It is an agonist of insect acetylcholine receptors (nAChRs) with Ki values of 1.9, 2.1, 290, and 50 nM for M. persicae and D. melanogaster receptors, rat brain membranes, and rat recombinant receptors containing α4β2 subunits, respectively.3,4 Imidacloprid is lethal to M. persicae with LD95 values of approximately 2 and 160 pg/aphid via oral and topical administration, respectively.2 It impairs aversive learning and memory retention in honey bees following chronic sublethal exposure of 20.8 ppb.5 In a mouse model of high-fat diet-induced obesity, imidacloprid (0.06-6 mg/kg per day) increases body weight gain and adiposity and impairs glucose metabolism without increasing total food intake.6 Formulations containing imidacloprid have been used as insecticides in residential, veterinary, and agricultural settings.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Elbert, A., Overbeck, H., Iwaya, K., et alImidacloprid, a novel systemic nitromethylene analogue insecticide for crop protection. Brighton Crop Protection Conference, Pests and Diseases 21-28 (1990).

    2. Elbert, A., Becker, B., Hartwig, J., et alImidacloprid - A new systemic insecticide. Pflanzenschutz-Nachrichten Bayer (German Edition) 44(2), 113-136 (1991).

    3. Kagabu, S., Maienfisch, P., Zhang, A., et al5-Azidoimidacloprid and an acyclic analogue as candidate photoaffinity probes for mammalian and insect nicotinic acetylcholine receptors. J. Med. Chem. 43(26), 5003-5009 (2000).

    4. Tomizawa, M., and Casida, J.E. Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors. Annu. Rev. Entomol. 48, 339-364 (2003).

    5. Zhang, E., and Nieh, J.C. The neonicotinoid imidacloprid impairs honey bee aversive learning of simulated predation. J. Exp. Biol. 218(Pt 20), 3199-3205 (2015).

    6. Sun, Q., Xiao, X., Kim, Y., et alImidacloprid promotes high fat diet-induced adiposity and insulin resistance in male C57BL/6J mice. J. Agric. Food Chem. 64(49), 9293-9306 (2016).