Putrescine

Chembox new
ImageFile=Diaminobutane.pngImageSize=
ImageName=Putrescine
ImageFile1=Putrescine-stickAndBall.pngImageSize1=
ImageName1=Putrescine 3D
IUPACName=butane-1,4-diamine
OtherNames=
Section1= Chembox Identifiers
CASNo=110-60-1
PubChem=1045
SMILES=NCCCCN
MeSHName=Putrescine
Section2= Chembox Properties
Formula=C₄H₁₂N₂
MolarMass=88.1516
Appearance=
Density=
MeltingPt={melting_point|27} °C
BoilingPt={boiling_point|158-160} °C
Solubility=
Section3= Chembox Hazards
MainHazards=
FlashPt=
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Putrescine (sometimes spelled putrescin or putrescene) is an organic chemical compound NH₂(CH₂)₄NH₂ (1,4-diaminobutane or butanediamine). It is related to cadaverine; both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses. [cite book | last =Lewis | first =Robert Alan | title =Lewis' Dictionary of Toxicology | publisher =CRC Press | date =1998 | isbn =1566702232|pages=212 ] [cite book | last =Kamhi | first =Ellen, Ph.D., RN, HNC | title =Alternative Medicine Magazine's Definitive Guide to Weight Loss | publisher =Celestial Arts | date =2007 | pages =14 | isbn = 1587612593|quote=Ornithine is converted by bowel bacteria into a toxic substance called putrescine, which in turn degrades into polyamines, such as spermadine, spermine, and cadaverine (literally meaning "the essence of dead cadavers").] The two compounds are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. They are also found in semen and some microalgae, together with related molecules like spermine and spermidine.

History

Putrescine and cadaverine were first described by the Berlinese physician Ludwig Brieger in 1885.

Production and use

Putrescine is produced on industrial scale by hydrogenation of succinonitrile, which is produced by addition of hydrogen cyanide to acrylonitrile. Putrescine is reacted with adipic acid to yield the polyamide Nylon-4,6, which is marketed by DSM under the trade name Stanyl.

Biochemistry

Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another s-adenosyl methionine and converts it to spermine.

Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. The polyamines, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division.

Toxicity

Putrescine is toxic in large doses. In rats it had a fairly low acute oral toxicity of 2000 mg/kg body weight [http://cat.inist.fr/?aModele=afficheN&cpsidt=2714745] .

Cultural references

Putrescine is featured as a non-lethal weapon in the science fiction novel Zodiac, by Neal Stephenson. Its use is also suggested as a practical joke in [http://www.qwantz.com/archive/001155.html an episode] of Dinosaur Comics.

Notes

References

*cite encyclopedia
encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry
title = Nitriles
url = http://www.mrw.interscience.wiley.com/emrw/9783527306732/ueic/article/a17_363/current/html?hd=All%2Csuccinonitrile
accessdate = 2007-09-10
edition = 7th Ed.
*cite web
url = http://www.dsm.com/en_US/html/dep/stanyl.htm
title = DSM Engineering Plastics
accessdate = 2007-09-10

External links

* [http://www.chm.bris.ac.uk/sillymolecules/sillymols.htm Molecules with silly names]