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 ...

pelargonic acid Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula CH3(CH2)7CO2H. It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, ...

and morpholine.

Properties

4-Nonanoylmorpholine was first synthetized in 1954 by L. M. Rice, from morpholine and acyl chloride 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 miscib ...

propanol There are two isomers of propanol. *1-Propanol, ''n''-propanol, or propan-1-ol : CH3CH2CH2OH, the most common meaning *2-Propanol, Isopropyl alcohol Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a c ...

, and

dimethyl formamide Dimethylformamide is an organic compound with the formula ( CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the major ...

) 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 formulations containing

CR gas CR gas or dibenzoxazepine (chemical name dibenz 'b'',''f''1,4]oxazepine, is an incapacitating agent and a lachrymatory agent. CR was developed by the British Ministry of Defence as a riot control agent in the late 1950s and early 1960s. A report ...

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 le ...

'' mosquitoes.Pherobase entry
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Notes

References

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