Alan Yanahan CPSC 270, 2009 Imidacloprid A Neonicotinoid.

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Alan Yanahan CPSC 270, 2009 Imidacloprid A Neonicotinoid

History Late 1970s: chemists at Shell Chemical Company laid the groundwork for the future synthesis of imidacloprid through their investigations of potential insecticides 1984: chemists as Nikon Bayer Agrochem create imidacloprid First neonicotinoid insecticide registered for use

Imidacloprid Compared to nicotine Systemic insecticide Less human toxicity and greater effectiveness against insects Systemic insecticide Used on a wide variety of fruit and vegetable crops Used in termite control and in flea control on pets

How Does Imidacloprid Work? Have to understand the nervous system first

The Nervous System Nerve cells transmit messages from one another by means of electrical impulses (action potentials) The axon carries the message away from one nerve cell to the dendrites of another nerve cell

The Nervous System Between the axon and dendrite is a gap referred to as the synapse In order for the electrical message to cross the synapse, it must be converted into a chemical message

The Nervous System When an electrical impulse reaches the end of an axon, it leads to the release of chemicals called neurotransmitters These neurotransmitters bind with receptors on the dendrites of neighboring nerve cells to cause the generation of another electrical impulse Enzymes break down neurotransmitters to prevent nerve cells from repeatedly firing

What Does This Look Like?

Vesicle releases acetylcholine (neurotransmitter) into nerve synapse Acetylcholine binds with the enzyme acetylcholinesterase Axon of pre-synaptic cell receives action potential and voltage gated Ca2+ channel opens Voltage gated Ca2+ channel closes Acetylcholine Vesicle Na+ Na+ Choline is released Ca2+ Acetylcholine is released from nicotinic acetylcholine receptor Calcium ions (Ca2+) enter axon Nicotinic acetylcholine receptor opens Na+ Ca2+ Ca2+ Acetate is released Nicotinic acetylcholine receptor closes Sodium ions (Na+) enter the dendrite and cause an action potential in post-synaptic cell Acetylcholine binds with receptor (nicotinic acetylcholine receptor)

When Imidacloprid is Present in the Synapse Imidacloprid mimics the molecular shape of the neurotransmitter acetylcholine Acts on various nicotinic acetylcholine receptors to cause nerves to fire Is not recognized by the enzyme acetylcholinesterase Leads to tremors, convulsion, and death in insects

What Does This Look Like?

Acetylcholine binds with the enzyme acetylcholinesterase Ca2+ Ca2+ Ca2+ Choline is released Na+ Acetylcholine is released from nicotinic acetylcholine receptor Na+ Acetylcholine Nicotinic acetylcholine receptor opens Na+ Acetate is released Imidacloprid binds with the nicotinic acetylcholine receptor Sodium ions (Na+) enter the dendrite to produce another action potential Nicotinic acetylcholine receptor closes Na+ Na+ Na+

Sources Kreiger, Robert I. Handbook of Pesticide Toxicology 2nd Edition: Agents. Sheets, Larry P. Chapter 54—Imidacloprid: A Neonicotinoid Insecticide. San Diego: Academic Press, 2001 Silverthorn, Dee Unglaub. Human Physiology An Integrated Approach 4th Edition. San Francisco: Pearson Education Inc., 2007.