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Cadaverine information


Cadaverine
Skeletal formula of cadaverine
Skeletal formula
Ball and stick model of cadaverine
Ball-and-stick model[1]
Names
Preferred IUPAC name
Pentane-1,5-diamine
Other names
1,5-Diaminopentane, pentamethylenediamine
Identifiers
CAS Number
  • 462-94-2 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B00334
Beilstein Reference
1697256
ChEBI
  • CHEBI:18127 checkY
ChEMBL
  • ChEMBL119296 checkY
ChemSpider
  • 13866593 checkY
DrugBank
  • DB03854 checkY
ECHA InfoCard 100.006.664 Edit this at Wikidata
EC Number
  • 207-329-0
Gmelin Reference
2310
KEGG
  • C01672 checkY
MeSH Cadaverine
PubChem CID
  • 273
RTECS number
  • SA0200000
UNII
  • L90BEN6OLL checkY
UN number 2735
CompTox Dashboard (EPA)
  • DTXSID5075448 Edit this at Wikidata
InChI
  • InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 checkY
    Key: VHRGRCVQAFMJIZ-UHFFFAOYSA-N checkY
SMILES
  • NCCCCCN
Properties
Chemical formula
C5H14N2
Molar mass 102.181 g·mol−1
Appearance Colourless liquid
Odor Unpleasant
Density 873,0 g/l
Melting point 11.83[2] °C (53.29 °F; 284.98 K)
Boiling point 179.1 °C; 354.3 °F; 452.2 K
Solubility in water
Soluble
Solubility in other solvents conventional organic solvents
log P −0.123
Acidity (pKa) 10.25, 9.13
Refractive index (nD)
1.458
Hazards
GHS labelling:
Pictograms
GHS05: Corrosive
Signal word
Danger
Hazard statements
H314
Precautionary statements
P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point 62 °C (144 °F; 335 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
2000 mg/kg (oral, rat)
Related compounds
Related alkanamines
  • n-Butylamine
  • Putrescine
  • Pentylamine
  • Hexamethylenediamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Cadaverine is an organic compound with the formula (CH2)5(NH2)2. Classified as a diamine, it is a colorless liquid with an unpleasant odor.[3] It is present in small quantities in living organisms but is often associated with the putrefaction of animal tissue. Together with putrescine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.

  1. ^ Thalladi, V.R.; Boese, R.; Weiss, H.-C. (2001). "CSD Entry: QATWEN : 1,5-Pentanediamine". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/cc4g861. Retrieved 2021-11-07.
  2. ^ Thalladi, V. R.; Boese, R.; Weiss, H. C. (2000). "The Melting Point Alternation in α,ω-Alkanediols and α,ω-Alkanediamines: Interplay between Hydrogen Bonding and Hydrophobic Interactions". Angew. Chem. Int. Ed. 39 (5): 918–922. doi:10.1002/(SICI)1521-3773(20000303)39:5<918::AID-ANIE918>3.0.CO;2-E. PMID 10760893.
  3. ^ Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 978-3527306732.

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Cadaverine

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Cadaverine is an organic compound with the formula (CH2)5(NH2)2. Classified as a diamine, it is a colorless liquid with an unpleasant odor. It is present...

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Putrescine

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melts near room temperature. It is classified as a diamine. Together with cadaverine, it is largely responsible for the foul odor of putrefying flesh, but...

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Carrion

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exude a foul odor caused by the presence of bacteria and the emission of cadaverine and putrescine. Some plants and fungi smell like decomposing carrion and...

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Sparteine

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labeled cadaverine have shown three units of cadaverine are incorporated into sparteine and two of the C-N bonds from two of the cadaverine units remain...

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Health risks from dead bodies

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intestinal pathogens, tuberculosis, cholera and others. The substances cadaverine and putrescine are produced during the decomposition of animal (including...

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Diamine

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carbons: putrescine (butane-1,4-diamine) 5 carbons: cadaverine (pentane-1,5-diamine) Cadaverine 6 carbons: hexamethylenediamine (hexane-1,6-diamine)...

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Lysine decarboxylase

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The enzyme Lysine decarboxylase (EC 4.1.1.18) converts lysine to cadaverine. Abbreviated as Ldc, the enzyme is involved in acid-stress response in Enterobacteria...

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Enteroinvasive Escherichia coli

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loss of cadaverine synthesis, of ompT, and of curli formation. These features are probably acquired independently, as the two lost cadaverine synthesis...

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Putrefaction

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such as the functional-group amines putrescine (from ornithine) and cadaverine (from lysine), which carry the noxious odor of rotten flesh. Initially...

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Nitrogen

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creation of long-chain, nitrogen-containing amines, such as putrescine and cadaverine, which are breakdown products of the amino acids ornithine and lysine...

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List of chemical compounds with unusual names

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considered to be related to sex. Nordenström, Björn E. W. (1951). "Effect of cadaverine and lysine on the urinary excretion of piperidine in rabbits". Acta Pharmacologica...

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Stink bomb

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Triethylamine, old fish Ethanolamine, unpleasant Putrescine, rotten meat Cadaverine, rotten meat Heterocyclic compounds Indole, smelling of feces Skatole...

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Skatole

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1-Methylindole 2-Methylindole (methylketol) 5-Methylindole 7-Methylindole Cadaverine Oswald, Iain W. H.; Paryani, Twinkle R.; Sosa, Manuel E.; Ojeda, Marcos...

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Carrion flower

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and in other species, trace amounts of amines such as putrescine and cadaverine have been found. Methyl thioacetate (which has a cheesy, garlic-like odor)...

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Decarboxylation

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histidine to histamine serine to ethanolamine glutamic acid to GABA lysine to cadaverine arginine to agmatine ornithine to putrescine 5-HTP to serotonin L-DOPA...

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Cadaver

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their use in testing. Anatomy Act 1832 Andreas Vesalius Autopsy Body farm Cadaverine, a foul-smelling chemical released during decomposition Conservation and...

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Calcium carbonate

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peptides derived from biological calcium carbonate. Some polyamines such as cadaverine and Poly(ethylene imine) have been shown to facilitate the formation of...

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Semen

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environment. Basic amines such as putrescine, spermine, spermidine and cadaverine are responsible for the smell and flavor of semen. These alkaline bases...

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Polyimine

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Synthesis of a polyimine from terephthalaldehyde and cadaverine....

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Stages of death

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Decomposition – Bacteria grow throughout the body, releasing gases, including cadaverine, which in turn bloat the body and cause an unpleasant odor. Stage 3: Advanced...

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Nylon

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might be to use cadaverine (pentamethylenediamine), a chemical extracted from corpses. Although scientists asserted that cadaverine was also extracted...

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Carob

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wood. Male flowers on a carob tree in Cyprus, which emanate a strong cadaverine odor Close-up of female flower on the carob tree Green carob fruit pods...

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Corpse decomposition

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bloat, and producing foul-smelling chemicals including putrescine and cadaverine. Cells in tissues break down and release hydrolytic enzymes, and the top...

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C5H14N2

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C5H14N2 (molar mass: 102.17 g/mol, exact mass: 102.1157 u) may refer to: Cadaverine Dimethylaminopropylamine (DMAPA) N,N′-Dimethyl-1,3-propanediamine (DMPA)...

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Cysteine

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proline→ 1-Pyrroline-5-carboxylic acid arginine→ Agmatine Ornithine Citrulline Cadaverine Putrescine other cysteine+glutamate→glutathione: γ-Glutamylcysteine...

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Glutathione

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proline→ 1-Pyrroline-5-carboxylic acid arginine→ Agmatine Ornithine Citrulline Cadaverine Putrescine other cysteine+glutamate→glutathione: γ-Glutamylcysteine...

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Decomposition

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breakdown of tissues by bacteria. These processes release compounds such as cadaverine and putrescine, that are the chief source of the unmistakably putrid odor...

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Stapelia gigantea

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flowers responsible for their odour include diamines (putrescine and cadaverine), sulfur compounds and various phenolic molecules. Because of the foul...

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Creatinine

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proline→ 1-Pyrroline-5-carboxylic acid arginine→ Agmatine Ornithine Citrulline Cadaverine Putrescine other cysteine+glutamate→glutathione: γ-Glutamylcysteine...

Word Count : 2176

Glycine

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proline→ 1-Pyrroline-5-carboxylic acid arginine→ Agmatine Ornithine Citrulline Cadaverine Putrescine other cysteine+glutamate→glutathione: γ-Glutamylcysteine...

Word Count : 3236

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