4-Nonanoylmorpholine ''pelargonic acid morpholide, N-nonanoylmorpholine, MPK or МПК (for russian: морфолид пеларгоновой кислоты), or MPAis an

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it i ...

of pelargonic acid and

morpholine Morpholine is an organic chemical compound having the chemical formula O( C H2CH2)2 NH. This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. Fo ...

Properties

4-Nonanoylmorpholine was first synthetized in 1954 by L. M. Rice, from

and

acyl chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example o ...

of pelargonic acid. It is a liquid insoluble in water and soluble in polar organic solvents (e.g.

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscibl ...

, propanol, and dimethyl formamide) and fats. Its volatility is 27 mg/m³ at 20 °C and 43 mg/m³ at 35 °C.

Uses

It is a used as a solvent in

lachrymatory Lachrymatory or lacrymatory may refer to: * Something that has the effect of ''lachrymation'', causing the secretion of tears * Tear gas Tear gas, also known as a lachrymator agent or lachrymator (), sometimes colloquially known as "mace" af ...

formulations containing CR gas or

CS gas The compound 2-chlorobenzalmalononitrile (also called ''o''-chlorobenzylidene malononitrile; chemical formula: C10H5ClN2), a cyanocarbon, is the defining component of tear gas commonly referred to as CS gas, which is used as a riot control agen ...

. It is reported to be effective against dogs and starts being effective in concentrations of over 20–40 mg•min/m³. It is considered very safe, with high differences between effective and toxic concentrations. At one time it was reportedly used as food seasoning with no reported adverse effects. However, its effectiveness when used alone is rather low even in the highest permitted concentration, so it is almost always used in combination with CR gas or CS gas, commonly referred to as

tear gas Tear gas, also known as a lachrymator agent or lachrymator (), sometimes colloquially known as "mace" after the early commercial aerosol, is a chemical weapon that stimulates the nerves of the lacrimal gland in the eye to produce tears. In ...

. In that combination, this blend is effective even against dogs and people under influence of alcohol or other drugs. Its effect usually lasts for 15–30 minutes. MPK blends with CR gas or CS gas are common personal

self-defense Self-defense (self-defence primarily in Commonwealth English) is a countermeasure that involves defending the health and well-being of oneself from harm. The use of the right of self-defense as a legal justification for the use of force ...

chemical agents in Russia and Ukraine, but is virtually unknown elsewhere. 4-Nonanoylmorpholine has been reported to have

insect repellent An insect repellent (also commonly called "bug spray") is a substance applied to skin, clothing, or other surfaces to discourage insects (and arthropods in general) from landing or climbing on that surface. Insect repellents help prevent and cont ...

properties in ''

Aedes aegypti ''Aedes aegypti'', the yellow fever mosquito, is a mosquito that can spread dengue fever, chikungunya, Zika fever, Mayaro and yellow fever viruses, and other disease agents. The mosquito can be recognized by black and white markings on its l ...

'' mosquitoes.Pherobase entry
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Notes

References

* {{DEFAULTSORT:Nonanoylmorpholine, 4- Incapacitating agents Lachrymatory agents Insect repellents Morpholines Carboxamides