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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
CAS number 5299-64-9
PubChem 79182
InChI InChI=1/C13H25NO2/c1-2-3-4-5-6-7-8- 13(15)14-9-11-16-12-10-14/h2-12H2,1H3
Molecular formula C13H25NO2
Molar mass 227.34 g/mol
Appearance Liquid
Boiling point

310 - 315 °C

Solubility in water Insoluble
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. It is effective against dogs. It 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. However, its effectiveness when used alone is rather low 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 and people under influence of alcohol or drugs. Its effect usually lasts for 15-30 minutes.

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

Natural occurrence

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


  1. ^ Pherobase entry
  • Collum D.B., Chen S.-C., Ganem B. (1978). "A new synthesis of amides and macrocyclic lactams". J. Org. Chem. 43 (22): 4393-4394(2). doi:10.1021/jo00416a040. Retrieved on 2007-07-06.
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "4-Nonanoylmorpholine". A list of authors is available in Wikipedia.
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