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{{CMG}}
{{CMG}}


==Overview==
==Overview==
'''PETN''' (''pentaerythritol tetranitrate'', also known as ''pentrite'', or rarely and primarily in German as ''nitropenta'') is one of the most powerful high explosives known, with a [[relative effectiveness factor]] (R.E. factor) of 1.66. It is more sensitive to shock or friction than [[Trinitrotoluene|TNT]] or [[tetryl]], and it is never used alone as a booster. It is primarily used in booster and bursting charges of small caliber ammunition, in upper charges of detonators in some land mines and shells, and as the explosive core of detonation cord.
Like [[nitroglycerin]] (glyceryl trinitrate) and other nitrates, PETN is also used medically as a [[vasodilator]] in the treatment of [[heart disease|heart conditions]].<ref name = newdrugs/><ref name=ebadi/> These drugs work by releasing the signaling gas [[nitric oxide]] in the body. The heart medicine ''Lentonitrat'' is nearly pure PETN.<ref>{{cite journal|title = The therapeutic role of coronary vasodilators: glyceryl trinitrate, isosorbide dinitrate, and pentaerythritol tetranitrate.|author = Russek H. I.| journal =American Journal of Medical Science| volume = 252| issue = 1| pages = 9–20|year = 1966| pmid = 4957459|doi = 10.1097/00000441-196607000-00002}}</ref>
 
PETN is also used as a [[vasodilator]], similar to [[Glyceryl trinitrate (pharmacology)]]. The [[medicine]] for [[heart disease]]s, "Lentonitrat", is pure PETN.<ref>{{cite journal|title = The therapeutic role of coronary vasodilators: glyceryl trinitrate, isosorbide dinitrate, and pentaerythritol tetranitrate. | author = Russek H. I.| journal =American Journal of Medical Science| volume = 252| issue = 1| pages = 9-20|year = 1966| id = PMID 4957459 }}</ref>
 
==Properties==
The velocity of detonation of PETN at a density of 1.7 g/cm³ is 8,400 meters per second. The heat of explosion is 5,862 kilojoules per kilogram<ref>Erich Ammedick: ''Militärchemie. eine Einführung.'' 4. Auflage. In: ''Bausteine der Chemie.'' VEB Deutscher Verlag für Grundstoffindustrie, Leipzig 1980, ISBN 978-3342000372 (German)</ref>, or 1.5 times that of [[Trinitrotoluene|TNT]].
 
PETN's formula is C(CH<sub>2</sub>ONO<sub>2</sub>)<sub>4</sub>. Its theoretical maximum crystal density is 1.773 g/cm³.  It melts at 141 °C.
 
==As a pollutant in the environment==
PETN does not occur naturally, so the production of this kind of compound without detonation may lead to contamination of the environment. PETN is subject to [[biodegradation]] in untreated or unpreserved urine and feces. There also have been some reports of its degradation by [[bacteria]], whose PETN reductase denitrates PETN into trinitrates and then dinitrates (French et al., 1996). The last compound shown in the pathway, pentaerythritol dinitrate, is degraded further to unknown products.
 
==Production==
PETN's preparation involves the nitration of [[pentaerythritol]] with a mixture of concentrated [[Nitric acid|nitric]] and [[sulfuric acid]]. The preferred method of nitration is the ICI method, which utilizes concentrated nitric acid (98%+) alone, as mixed acid can create unstable sulfonated by-products.<br>
 
C(CH<sub>2</sub>OH)<sub>4</sub> + 4HNO<sub>3</sub> &rarr; C(CH<sub>2</sub>ONO<sub>2</sub>)<sub>4</sub> + 4H<sub>2</sub>O<br>


==History==
Monitoring of oral usage of the drug by patients has been performed by determination of plasma levels of several of its hydrolysis products, pentaerythritol dinitrate, pentaerythritol mononitrate and pentaerythritol, in plasma using [[gas chromatography-mass spectrometry]].<ref>R. Baselt, ''Disposition of Toxic Drugs and Chemicals in Man'', 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1201–1203.</ref>
Penthrite was first synthesized in 1891 by Tollens and Wiegand by nitration of [[pentaerythritol]]. In 1912, after being patented by the German government, the production of PETN started. PETN was used by the German army in World War I. <ref>{{cite book|title = Die Schiess- und Sprengstoffe | author = Stettbacher, Alfred| 2. völlig umgearb. Aufl.
|place =  Leipzig |publisher= Barth|year = 1933| pages= 459 }}</ref> PETN is also one of the ingredients in Semtex plastic explosive.


==See also==
*[[RDX]]
*[[trinitrotoluene|TNT]]


==References==
==References==
{{Reflist}}
{{reflist|colwidth=30em}}


==Additional Resources==
==Additional Resources==
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[[Category:Alkyl nitrates]]
[[Category:Alkyl nitrates]]
[[Category:Antianginals]]
[[Category:Antianginals]]
[[Category:Cardiovascular Drugs]]
[[Category:Drugs]]
[[Category:Drugs]]


Revision as of 19:53, 24 July 2014

Template:Explosivebox

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Like nitroglycerin (glyceryl trinitrate) and other nitrates, PETN is also used medically as a vasodilator in the treatment of heart conditions.[1][2] These drugs work by releasing the signaling gas nitric oxide in the body. The heart medicine Lentonitrat is nearly pure PETN.[3]

Monitoring of oral usage of the drug by patients has been performed by determination of plasma levels of several of its hydrolysis products, pentaerythritol dinitrate, pentaerythritol mononitrate and pentaerythritol, in plasma using gas chromatography-mass spectrometry.[4]


References

  1. ↑ Invalid <ref> tag; no text was provided for refs named newdrugs
  2. ↑ Invalid <ref> tag; no text was provided for refs named ebadi
  3. ↑ Russek H. I. (1966). "The therapeutic role of coronary vasodilators: glyceryl trinitrate, isosorbide dinitrate, and pentaerythritol tetranitrate". American Journal of Medical Science. 252 (1): 9–20. doi:10.1097/00000441-196607000-00002. PMID 4957459.
  4. ↑ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1201–1203.

Additional Resources

  • Cooper, Paul W., Explosives Engineering, New York: Wiley-VCH, 1996. ISBN 0-471-18636-8

External links

Template:Antianginals (nitrates)

cs:Pentrit de:Nitropenta eo:PETN it:Tetranitrato di pentaeritrite he:PETN lv:Tetranitropentaeritrīts lt:PETN hu:Pentaeritrit-tetranitrát sk:Pentrit sl:Pentrit fi:PETN sv:Pentyl (sprängämne)


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