4-Nonanoylmorpholine
From Wikipedia, the free encyclopedia
| 4-Nonanoylmorpholine | |
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| Systematic name | 4-Nonanoylmorpholine |
| Chemical formula | CxHxNxOx |
| Molecular mass | xx.xx g/mol |
| Density | x.xxx g/cm³ |
| Melting point | xx.x °C |
| Boiling point | 310-315 °C |
| volatility | 27 mg/m3 (20 °C) 43 mg/m3 (35 °C) |
| CAS number | [5299-64-9] |
| SMILES | CCCCCCCCC(N1CCOCC1)=O |
| 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. It is reportedly an irritating agent and a lachrymatory agent developed in Russia as an alternative to capsaicin-based pepper spray.[citation needed]
It is a liquid with boiling point of 310-315 °C. It is 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 was first synthetized in 1954 by L.M. Rice, from morpholine and chloroanhydride of pelargonic acid.
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.
Together with CS gas it is the active ingredient of Teren-4M, a pepper spray aerosol used by Ukrainian police.[citation needed]
MPK is a common personal self-defense chemical agent in Russia and Ukraine, but is virtually unknown elsewhere.
[edit] Natural occurrence
4-Nonanoylmorpholine naturally occurs as a pheromone of Aedes aegypti mosquitoes.
