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Template:Chembox E numberTemplate:Chembox SolubilityInWater
IUPAC name 4-Nonanoylmorpholine
Other names 4-(1-Oxononyl)morpholine, N-Nonanoylmorpholine, 1-(4-Morpholino)-1-nonanone, 4-Morpholinenonylic acid, Pelargonic acid morpholide, Pelargonic morpholide, N-Morpholino nonanamide, 1-Morpholin-4-ylnonan-1-one, MPA, MPK
3D model (JSmol)
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Molar mass 227.34 g/mol
Appearance Liquid
Boiling point
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

4-Nonanoylmorpholine (pelargonic acid morpholide, N-nonanoylmorpholine, MPK or МПК (for морфолид пеларгоновой кислоты), or MPA) is an amide of pelargonic acid and morpholine.


4-Nonanoylmorpholine was first synthetized in 1954 by L.M. Rice, from morpholine and chloroanhydride of pelargonic acid.

It is a liquid insoluble in water and soluble in polar organic solvents (eg. acetone, propanol, dimethyl formamide, and benzene) and fats. Its volatility is 27 mg/m3 at 20 °C and 43 mg/m3 at 35 °C.


It is a lachrymatory agent with about 5 times the potency of chloroacetophenone. It is comparable to adamsite[citation needed]. It is effective against dogs. It starts being effective in concentrations of over 20-40 mg.min/m3. It is considered very safe[citation needed], with high differences between effective and toxic concentrations. At one time it was reportedly used as food seasoning. However, its effectiveness when used alone is rather low[citation needed] even in the highest permitted concentration, so it is often used in combination with CR gas or CS gas. In that combination, it is effective even against dogs[citation needed] and people under influence of alcohol or drugs[citation needed]. Its effect usually lasts for 15-30 minutes[citation needed].

MPK is a common[citation needed] personal self-defense chemical agent in Russia and Ukraine, but is virtually unknown elsewhere[citation needed].

Natural occurrence

4-Nonanoylmorpholine naturally occurs as a pheromone of Aedes aegypti mosquitoes.[1]


  • Collum D.B., Chen S.-C., Ganem B. (1978). "A new synthesis of amides and macrocyclic lactams" (PDF). J. Org. Chem. 43 (22): 4393-4394(2). doi:10.1021/jo00416a040. Retrieved 2007-07-06.

External links