Protein Information

Name acetylcholine receptor (protein family or complex)
Synonyms Acetylcholine receptor; Acetylcholine receptors

Compound Information

Name acetamiprid
CAS

Reference List

PubMed Abstract RScore(About this table)
12208819 Tomizawa M, Casida JE: Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors. Annu Rev Entomol. 2003;48:339-64. Epub 2002 Jun 4.

Imidacloprid (the principal example), nitenpyram, acetamiprid, thiacloprid, thiamethoxam, and others act as agonists at the insect nicotinic acetylcholine receptor (nAChR).
81(1,1,1,1) Details
12425057 Ishaaya I, Kontsedalov S, Mazirov D, Horowitz AR: Biorational agents--mechanism and importance in IPM and IRM programs for controlling agricultural pests. Meded Rijksuniv Gent Fak Landbouwkd Toegep Biol Wet. 2001;66(2a):363-74.

In addition, efforts have been made to develop compounds acting selectively on groups of insects by inhibiting or enhancing biochemical sites such as respiration (diafenthiuron), the nicotinyl acetylcholine receptors (imidacloprid and acetamiprid), the GABA receptors (avermectins), the salivary glands of sucking pests (pymetrozine) and others.
31(0,1,1,1) Details
15880574 Brunet JL, Badiou A, Belzunces LP: In vivo metabolic fate of [14C]-acetamiprid in six biological compartments of the honeybee, Apis mellifera L. Pest Manag Sci. 2005 Aug;61(8):742-8.

During the first hours, acetamiprid was mainly detected in nicotinic acetylcholine receptor-rich tissues: abdomen, thorax and head.
6(0,0,1,1) Details
9260539 Chao SL, Dennehy TJ, Casida JE: Whitefly (Hemiptera: Aleyrodidae) binding site for imidacloprid and related insecticides: a putative nicotinic acetylcholine receptor. J Econ Entomol. 1997 Aug;90(4):879-82.

Three related compounds (the nitromethylene analog of imidacloprid, acetamiprid, and nitenpyram) inhibit [3H] imidacloprid binding by 50% at 0.40, 2.9, and 57 nM, respectively.
3(0,0,0,3) Details
17561262 Tan J, Galligan JJ, Hollingworth RM: Agonist actions of neonicotinoids on nicotinic acetylcholine receptors expressed by cockroach neurons. Neurotoxicology. 2007 Jul;28(4):829-42. Epub 2007 Apr 20.

Based on maximum inward currents, neonicotinoids could be divided into two subgroups: (1) those with a heterocyclic ring in their electronegative pharmacophore moiety (i.e. nicotine, imidacloprid and thiacloprid) were relatively weak partial agonists causing only 20-25% of the maximum ACh current and (2) open chain compounds (i.e. acetamiprid, dinotefuran, nitenpyram, and clothiandin) which were much more effective agonists producing 60-100% of the maximum ACh current.
2(0,0,0,2) Details
16981889 Liu Z, Williamson MS, Lansdell SJ, Han Z, Denholm I, Millar NS: A nicotinic acetylcholine receptor mutation (Y151S) causes reduced agonist potency to a range of neonicotinoid insecticides. J Neurochem. 2006 Nov;99(4):1273-81. Epub 2006 Sep 18.

The agonist potency of several nicotinic agonists has been examined, including all of the neonicotinoid insecticides that are currently licensed for either crop protection or animal health applications (acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam).
2(0,0,0,2) Details
10789501 Wiesner P, Kayser H: Characterization of nicotinic acetylcholine receptors from the insects Aphis craccivora, Myzus persicae, and Locusta migratoria by radioligand binding assays: relation to thiamethoxam action. J Biochem Mol Toxicol. 2000;14(4):221-30.

In all three insects, the other neonicotinoid insecticides studied competed with [3-H]-imidacloprid in the same order: thiacloprid > imidacloprid > or = acetamiprid > nitenpyram.
2(0,0,0,2) Details
9453215 Tomizawa M, Casida JE: [125I] Azidonicotinoid photoaffinity labeling of insecticide-binding subunit of Drosophila nicotinic acetylcholine receptor. Neurosci Lett. 1997 Nov 21;237(2-3):61-4.

The goal of this study is to identify the ligand- and insecticide-binding subunit of Drosophila nAChR with a novel [125I] azidonicotinoid ([125I] AN) photoaffinity probe modeled on imidacloprid. [125I] AN photoaffinity labels a single polypeptide in Drosophila head membranes corresponding in molecular mass to 66 kDa at a specific site inhibited by various cholinergic ligands including (-)-nicotine, cytisine, carbachol, alpha-bungarotoxin and d-tubocurarine as well as the insecticides imidacloprid and acetamiprid, pharmacologically consistent with the ligand- and insecticide-binding subunit.
2(0,0,0,2) Details
10936213 Zhang A, Kayser H, Maienfisch P, Casida JE: Insect nicotinic acetylcholine receptor: conserved neonicotinoid specificity of [(3) H] imidacloprid binding site. J Neurochem. 2000 Sep;75(3):1294-303.

The chlorothiazolyl substituent generally confers higher potency in the clothianidin and desmethylthiamethoxam series and the chloropyridinyl moiety in the imidacloprid, thiacloprid, acetamiprid, and nitenpyram series.
2(0,0,0,2) Details
19069132 Todani M, Kaneko T, Hayashida H, Kaneda K, Tsuruta R, Kasaoka S, Maekawa T: [Acute poisoning with neonicotinoid insecticide acetamiprid] . Chudoku Kenkyu. 2008 Oct;21(4):387-90.

Neonicotinoids act as selective agonists at the nicotinic acetylcholine receptors, therefore their toxicity is higher to insect pests than to humans.
1(0,0,0,1) Details
15481821 Kayser H, Lee C, Decock A, Baur M, Haettenschwiler J, Maienfisch P: Comparative analysis of neonicotinoid binding to insect membranes: I. Pest Manag Sci. 2004 Oct;60(10):945-58.

Neonicotinoids bind selectively to insect nicotinic acetylcholine receptors with nanomolar affinity to act as potent insecticides.
Competitive neonicotinoids were acetamiprid, nitenpyram, thiacloprid, clothianidin and nithiazine, whereas thiamethoxam and the N-methyl analogues of imidacloprid and clothianidin showed non-competitive inhibition.
1(0,0,0,1) Details
10369463 Tomizawa M, Casida JE: Minor structural changes in nicotinoid insecticides confer differential subtype selectivity for mammalian nicotinic acetylcholine receptors. Br J Pharmacol. 1999 May;127(1):115-22.

The commercial insecticides (IMI, acetamiprid and nitenpyram) have low to moderate potency at the alpha3 and purported alpha4beta2 nicotinic AChRs and are essentially inactive at alpha1 and alpha7 nicotinic AChRs.
1(0,0,0,1) Details
12233176 Nauen R, Stumpf N, Elbert A: Toxicological and mechanistic studies on neonicotinoid cross resistance in Q-type Bemisia tabaci (Hemiptera: Aleyrodidae). Pest Manag Sci. 2002 Sep;58(9):868-75.

One of the latest group of insecticides introduced to the market were the neonicotinoids (chloronicotinyls), acting agonistically on insect nicotinic acetylcholine receptors.
Our study revealed that neonicotinoid-resistant Q-type strains from Almeria were often more than 100-fold less susceptible to thiamethoxam, acetamiprid and imidacloprid when tested in discontinuous systemic laboratory bioassays.
1(0,0,0,1) Details
14667058 Zewen L, Zhaojun H, Yinchang W, Lingchun Z, Hongwei Z, Chengjun L: Selection for imidacloprid resistance in Nilaparvata lugens: cross-resistance patterns and possible mechanisms. Pest Manag Sci. 2003 Dec;59(12):1355-9.


The selected resistant strain showed obvious cross-resistance to all the acetylcholine receptor targeting insecticides tested (monosultap 1.44-fold, acetamiprid 1.61-fold, imidacloprid homologues JS599 2.46-fold and JS598 3.17-fold), but not to others.
0(0,0,0,0) Details
14635178 Rauch N, Nauen R: Identification of biochemical markers linked to neonicotinoid cross resistance in Bemisia tabaci (Hemiptera: Aleyrodidae). Arch Insect Biochem Physiol. 2003 Dec;54(4):165-76.


Only monooxygenase activity correlated with imidacloprid, thiamethoxam and acetamiprid resistance and, therefore, monooxygenases seem to be the only enzyme system responsible for neonicotinoid resistance in B. tabaci Q- and B-types.
0(0,0,0,0) Details
16637697 Honda H, Tomizawa M, Casida JE: Insect nicotinic acetylcholine receptors: neonicotinoid binding site specificity is usually but not always conserved with varied substituents and species. J Agric Food Chem. 2006 May 3;54(9):3365-71.


The diversity of neonicotinoid insecticides acting as insect nicotinic acetylcholine (ACh) receptor (nAChR) agonists is illustrated by imidacloprid (IMI) with chloropyridinylmethyl (CPM) and N-nitroimine substituents, dinotefuran (DIN) with tetrahydrofurylmethyl (TFM) and N-nitroimine moieties, and acetamiprid (ACE) with CPM and N-cyanoimine groups.
0(0,0,0,0) Details