An active metabolite of imidacloprid
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Parent Compound(s)
24130Imidacloprid
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Desnitro-imidacloprid

Item No. 46092

Technical Information
Formal Name
1-[(6-chloro-3-pyridinyl)methyl]-4,5-dihydro-1H-imidazol-2-amine
CAS Number
115970-17-7
Synonyms
  • DNIMI
Molecular Formula
C9H11ClN4
Formula Weight
Purity
≥98%
A solid
Acetonitrile:Water (1:1): Slightly soluble: 0.1-1 mg/ml
SMILES
ClC1=NC=C(CN2C(N)=NCC2)C=C1
InChi Code
InChI=1S/C9H11ClN4/c10-8-2-1-7(5-13-8)6-14-4-3-12-9(14)11/h1-2,5H,3-4,6H2,(H2,11,12)
InChi Key
UEQZFAGVRGWPDK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Desnitro-imidacloprid (DNIMI) is an active metabolite of the neonicotinoid insecticide imidacloprid (Item No. 24130).1 It selectively binds to mammalian α1γα1δβ1-, α3β2β4α5-, α4β2-, and α7 nicotinic acetylcholine receptors (nAChRs; IC50s = 11, 9.9, 14, and 8.2 nM, respectively) over D. melanogaster nAChRs (IC50 = 1,530 nM). Unlike imidacloprid, DNIMI is not toxic to D. melanogaster (LD50 = >5 µg/g) but is toxic to mice (LD50 = 6-9 mg/kg). DNIMI (200 µg/ml) decreases the growth of, induces rupture of, and reduces progesterone, testosterone, and estradiol levels in, isolated mouse antral follicles.2 It has been found in human urine and drinking water.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tomizawa, M., Lee, D.L., and Casida, J.E. Neonicotinoid insecticides: Molecular features conferring selectivity for insect versus mammalian nicotinic receptors. J. Agric. Food Chem. 48(12), 6016-6024 (2000).

    2. Mourikes, V.E., Santacruz Márquez, R., Deviney, A., et alImidacloprid and its bioactive metabolite, desnitro-imidacloprid, differentially affect ovarian antral follicle growth, morphology, and hormone synthesis in vitro. Toxics 11(4), 349 (2023).

    3. Wang, A., Mahai, G., Wan, Y., et alAssessment of imidacloprid related exposure using imidacloprid-olefin and desnitro-imidacloprid: Neonicotinoid insecticides in human urine in Wuhan, China. Environ. Int. 141, 105785 (2020).

    4. Wan, Y., Han, Q., Wang, Y., et alFive degradates of imidacloprid in source water, treated water, and tap water in Wuhan, central China. Sci. Total Environ. 741, 140227 (2020).