IDFP is an organophosphorus compound related to the

nerve agent Nerve agents, sometimes also called nerve gases, are a class of organic chemicals that disrupt the mechanisms by which nerves transfer messages to organs. The disruption is caused by the blocking of acetylcholinesterase (AChE), an enzyme that ...

sarin Sarin (NATO designation GB G-series, "B"">Nerve_agent#G-series.html" ;"title="hort for Nerve agent#G-series">G-series, "B" is an extremely toxic synthetic organophosphorus compound.inhibitor Inhibitor or inhibition may refer to: In biology * Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity * Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotra ...

for a number of different enzymes that normally serve to break down neurotransmitters, however the long

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloa ...

chain of IDFP makes it dramatically weaker as an inhibitor of

acetylcholinesterase Acetylcholinesterase ( HGNC symbol ACHE; EC 3.1.1.7; systematic name acetylcholine acetylhydrolase), also known as AChE, AChase or acetylhydrolase, is the primary cholinesterase in the body. It is an enzyme that catalyzes the breakdown of ac ...

(AChE), with an IC₅₀ of only 6300 nM, while it is a potent inhibitor of two enzymes monoacylglycerol lipase (MAGL), the primary

enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products ...

responsible for degrading the

endocannabinoid Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

2-arachidonoylglycerol 2-Arachidonoylglycerol (2-AG) is an endocannabinoid, an endogenous agonist of the CB1 receptor and the primary endogenous ligand for the CB2 receptor. It is an ester formed from the omega-6 fatty acid arachidonic acid and glycerol. It is present ...

(2-AG), and fatty acid amide hydrolase (FAAH), the primary enzyme that degrades the other main endocannabinoid

anandamide Anandamide (ANA), also known as ''N''-arachidonoylethanolamine (AEA), is a fatty acid neurotransmitter. Anandamide was the first endocannabinoid to be discovered: it participates in the body's endocannabinoid system by binding to cannabinoid r ...

. The IC₅₀ of IDFP is 0.8 nM at MAGL, and 3.0 nM at FAAH. Inhibition of these two enzymes causes markedly increased levels of both anandamide and 2-AG in the brain, resulting in increased cannabinoid signalling and typical cannabinoid behavioral effects in animal studies, while its lack of potency at AChE means that no cholinergic symptoms are produced. Despite its similar chemical structure to the banned nerve agents, the long alkyl chain of IDFP causes it to fall outside the definition of "toxic chemicals" under the

Chemical Weapons Convention The Chemical Weapons Convention (CWC), officially the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction, is an arms control treaty administered by the Organisation for ...

,CWC Schedule 1 Part A. Toxic Chemicals
and since it also does not exhibit the potent AChE inhibition of related organophosphorus compounds, IDFP is not subject to the same stringent legal controls.

References

{{Cannabinoids Hydrolase inhibitors Phosphonofluoridates Isopropyl esters

See also

References