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((chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477223226
| ImageFile = 4-nonanoylmorpholine.png
| ImageSize = 
| PIN = 1-(Morpholin-4-yl)nonan-1-one
| OtherNames = 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, 4-Nonanoylmorpholine, MPA, MPK
|Section1=((Chembox Identifiers
| ChemSpiderID_Ref = ((chemspidercite|correct|chemspider))
| ChemSpiderID = 71509
| InChI1 = 1/C13H25NO2/c1-2-3-4-5-6-7-8-13(15)14-9-11-16-12-10-14/h2-12H2,1H3
| InChIKey1 = NBRDJXSTGSUITP-UHFFFAOYAS
| SMILES1 = O=C(N1CCOCC1)CCCCCCCC
| StdInChI_Ref = ((stdinchicite|correct|chemspider))
| StdInChI = 1S/C13H25NO2/c1-2-3-4-5-6-7-8-13(15)14-9-11-16-12-10-14/h2-12H2,1H3
| StdInChIKey_Ref = ((stdinchicite|correct|chemspider))
| StdInChIKey = NBRDJXSTGSUITP-UHFFFAOYSA-N
| CASNo_Ref = ((cascite|correct|CAS))
| CASNo = 5299-64-9
| UNII_Ref = ((cascite|correct|CAS))
| UNII = 0D2NEP40LU
| PubChem = 79182
| SMILES = CCCCCCCCC(=O)N1CCOCC1
| InChI = 1/C13H25NO2/c1-2-3-4-5-6-7-8- 13(15)14-9-11-16-12-10-14/h2-12H2,1H3
  ))
|Section2=((Chembox Properties
| Formula = C<sub>13</sub>H<sub>25</sub>NO<sub>2</sub>
| MolarMass = 227.34 g/mol
| Appearance = Liquid
| Density = 
| MeltingPt = 
| BoilingPtC = 310 to 315
| BoilingPt_notes = 
| Solubility = Insoluble
  ))
|Section3=((Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = 
))
))

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

==Properties==
4-Nonanoylmorpholine was first synthesized 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]], [[Propan-1-ol|propanol]], and [[dimethyl formamide]]) and fats. Its [[volatility (chemistry)|volatility]] is 27&nbsp;mg/m<sup>3</sup> at 20&nbsp;°C and 43&nbsp;mg/m<sup>3</sup> at 35&nbsp;°C.

==Uses==
((more citations needed section|date=November 2007))
It is a used as a solvent in [[Tear gas|lachrymatory]] formulations containing [[CR gas]] or [[CS gas]]. It is reported to be effective against dogs and starts being effective in concentrations of over 20–40&nbsp;mg•min/m<sup>3</sup>. 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. <!-- see the linked source --> 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]]. In that combination, this blend is effective even against dogs and people under [[alcohol intoxication|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]] chemical agents in Russia and Ukraine, but is virtually unknown elsewhere.

4-Nonanoylmorpholine has been reported to have [[insect repellent]] properties in ''[[Aedes aegypti]]'' mosquitoes.<ref>[http://www.pherobase.com/database/compound/compounds-detail-4-nonanoylmorpholine.php Pherobase entry]</ref>

==Notes==
<references/>

==References==
((more footnotes|date=September 2015))
*((cite journal |author1=Collum D. B. |author2=Chen S.-C. |author3=Ganem B. | year= 1978 | title = A new synthesis of amides and macrocyclic lactams | journal = [[Journal of Organic Chemistry]]| volume = 43 | issue = 22 | pages = 4393–4394(2) | doi = 10.1021/jo00416a040 | url = http://www.chem.cornell.edu/dbc6/references/1.pdf | access-date = 2007-07-06 | archive-url = https://web.archive.org/web/20070611211202/http://www.chem.cornell.edu/dbc6/references/1.pdf| archive-date = June 11, 2007|url-status=dead))

((Chemical agents))

((DEFAULTSORT:Nonanoylmorpholine, 4-))
[[Category:Incapacitating agents]]
[[Category:Lachrymatory agents]]
[[Category:Insect repellents]]
[[Category:4-Morpholinyl compounds]]
[[Category:Carboxamides]]

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