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Putrescine (sometimes spelled putrescin or putrescene) is an organic chemical compound N
Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
2(C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
H2)4NH2 (1,4-diaminobutane or butanediamine). It is related to cadaverine
Cadaverine

Cadaverine is a foul-smelling molecule produced by protein hydrolysis during putrefaction of animal tissue. Cadaverine is a toxic diamine with the formula NH25NH2, which is similar to putrescine....
; both are produced by the breakdown of amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
s in living and dead organisms and both are toxic in large doses. 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.






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Putrescine (sometimes spelled putrescin or putrescene) is an organic chemical compound N
Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
2(C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
H2)4NH2 (1,4-diaminobutane or butanediamine). It is related to cadaverine
Cadaverine

Cadaverine is a foul-smelling molecule produced by protein hydrolysis during putrefaction of animal tissue. Cadaverine is a toxic diamine with the formula NH25NH2, which is similar to putrescine....
; both are produced by the breakdown of amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
s in living and dead organisms and both are toxic in large doses. 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
Semen

Semen is an organic fluid, also known as seminal fluid, that usually contains spermatozoon....
 and some microalgae, together with related molecules like spermine
Spermine

Spermine is a polyamine involved in cellular metabolism found in all Eukaryote. Formed from spermidine, it is found in a wide variety of organisms and tissues and is an essential growth factor in some Bacterium....
 and spermidine
Spermidine

Spermidine is a polyamine involved in cellular metabolism that can be used to stimulate the enzyme, T7 RNA polymerase, a type of RNA polymerase....
.

History

Putrescine and cadaverine were first described by the Berlin
Berlin

Berlin is the Capital of Germany city and one of sixteen States of Germany of Germany. With a population of 3.4 million within its city limits, Berlin is the country's largest city....
 physician Ludwig Brieger in 1885.

Production and use

Putrescine is produced on industrial scale by hydrogenation
Hydrogenation

Hydrogenation is the chemical reaction that results from the addition of hydrogen . The process is usually employed to a redox or Saturation organic compounds....
 of succinonitrile
Succinonitrile

Succinonitrile, also butanedinitrile, is a nitrile, with the chemical formula of C2H42. It is a colourless solid that melts at 57 ?C, hence its waxy consistency....
, which is produced by addition of hydrogen cyanide
Hydrogen cyanide

Hydrogen cyanide is a chemical compound with chemical formula HCN. A solution of hydrogen cyanide in water is called hydrocyanic acid. Hydrogen cyanide is a colorless, extremely poisonous, and highly volatility liquid that boiling slightly above room temperature at 26 Celsius ....
 to acrylonitrile
Acrylonitrile

Acrylonitrile is the chemical compound with the formula CH2CHCN. This pungent-smelling colorless liquid often appears yellow due to impurities....
. Putrescine is reacted with adipic acid
Adipic acid

Adipic acid is the organic compound with the chemical formula 42. From the industrial perspective, it is the most important dicarboxylic acid: About 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon....
 to yield the polyamide
Polyamide

A polyamide is a polymer containing monomers of amides joined by peptide bonds. They can occur both naturally, examples being proteins, such as wool and silk, and can be made artificially, examples being nylons, aramids, and sodium poly....
 Nylon
Nylon

Nylon is a generic designation for a family of synthetic polymers known generically as polyamides and first produced on February 28, 1935 by Wallace Carothers at DuPont....
-4,6, which is marketed by DSM
DSM (company)

DSM is a multinational company specialized in Life Sciences and Materials Sciences. Its headquarters are in Heerlen, the Netherlands. Originally a state-owned coal mining company , the activities of DSM are now grouped into five clusters:...
 under the trade name Stanyl.

Biochemistry

Putrescine attacks s-adenosyl methionine
S-Adenosyl methionine

S-Adenosyl methionine is a coenzyme involved in methyl group transfers. SAM was first discovered in Italy by G. L. Cantoni in 1952. It is made from adenosine triphosphate and methionine by methionine adenosyltransferase ....
 and converts it to spermidine
Spermidine

Spermidine is a polyamine involved in cellular metabolism that can be used to stimulate the enzyme, T7 RNA polymerase, a type of RNA polymerase....
. Spermidine in turn attacks another s-adenosyl methionine
S-Adenosyl methionine

S-Adenosyl methionine is a coenzyme involved in methyl group transfers. SAM was first discovered in Italy by G. L. Cantoni in 1952. It is made from adenosine triphosphate and methionine by methionine adenosyltransferase ....
 and converts it to spermine
Spermine

Spermine is a polyamine involved in cellular metabolism found in all Eukaryote. Formed from spermidine, it is found in a wide variety of organisms and tissues and is an essential growth factor in some Bacterium....
.

Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase
Ornithine decarboxylase

The enzyme ornithine decarboxylase participates in the urea cycle, and in the metabolism of glutathione and amino groups. In humans, this protein has 461 amino acids and forms a homodimer....
. The polyamine
Polyamine

The polyamines are organic compounds having two or more primary amino groups - such as putrescine, cadaverine, spermidine, and spermine - that are essential molecules in both eukaryotic and prokaryotic cells....
s, 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.

Cultural references

Putrescine is featured as a non-lethal weapon in the science fiction novel Zodiac
Zodiac (novel)

Zodiac: An Eco-Thriller is Neal Stephenson's second novel, which tells the story of an environmentalist, Sangamon Taylor, uncovering a conspiracy involving industrialist pollution and Satanists in Boston Harbor....
, by Neal Stephenson
Neal Stephenson

Neal Town Stephenson is an American writer, known for his speculative fiction works, which have been variously categorized science fiction, historical fiction, maximalism, cyberpunk, and postcyberpunk....
. Its use is also suggested as a practical joke
Practical joke

A practical joke or prank is a stunt or trick to purposely make someone feel foolish or victimized, usually for humor. Practical jokes differ from confidence tricks in that the victim finds out, or is let in on, the joke rather than being fooled into handing over money or other valuables....
 in of Dinosaur Comics
Dinosaur Comics

Dinosaur Comics is a constrained comics webcomic by Canada writer Ryan North. It is also known as "Qwantz", after the site's domain name, "qwantz.com"....
.