| 词条 | Cadaverine |
| 释义 |
| Watchedfields = changed | verifiedrevid = 443671098 | ImageFile = Cadaverine-2D-skeletal.png | ImageFile_Ref = {{chemboximage|correct|??}} | ImageSize = 200 | ImageName = Skeletal formula of cadaverine | ImageFile2 = Cadaverine-3D-balls.png | ImageFile2_Ref = {{chemboximage|correct|??}} | ImageSize2 = 160 | ImageName2 = Ball and stick model of cadaverine | PIN = Pentane-1,5-diamine | OtherNames = 1,5-Diaminopentane |Section1={{Chembox Identifiers | CASNo = 462-94-2 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 273 | ChemSpiderID = 13866593 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | UNII = L90BEN6OLL | UNII_Ref = {{fdacite|correct|FDA}} | EINECS = 207-329-0 | UNNumber = 2735 | DrugBank = DB03854 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | KEGG = C01672 | KEGG_Ref = {{keggcite|correct|kegg}} | MeSHName = Cadaverine | ChEBI = 18127 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEMBL = 119296 | ChEMBL_Ref = {{ebicite|correct|EBI}} | RTECS = SA0200000 | Beilstein = 1697256 | Gmelin = 2310 | 3DMet = B00334 | SMILES = NCCCCCN | StdInChI = 1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = VHRGRCVQAFMJIZ-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} }} |Section2={{Chembox Properties | C=5 | H=14 | N=2 | Appearance = Colourless to yellow oily liquid | Odor = Unbearably unpleasant to unpleasant | Density = 0.8730 g/mL | MeltingPtC = 11.83 | BoilingPtK = 452.2 | Solubility = Soluble | SolubleOther = Soluble in ethanol Slightly soluble in ethyl ether | Solvent = other solvents | LogP = −0.123 | RefractIndex = 1.458 | pKa = 10.25, 9.13 }} |Section3={{Chembox Hazards | ExternalSDS = | GHSPictograms = {{GHS corrosion}} | GHSSignalWord = DANGER | HPhrases = {{H-phrases|314}} | PPhrases = {{P-phrases|280|305+351+338|310}} | NFPA-H = 3 | NFPA-F = 2 | NFPA-R = 0 | FlashPtC = 62 | LD50 = 2000 mg/kg (oral, rat) }} |Section4={{Chembox Related | OtherFunction_label = alkanamines | OtherFunction = {{Unbulleted list|n-Butylamine|Putrescine|Pentylamine|Hexamethylenediamine}} }} }} Cadaverine is a foul-smelling diamine compound produced by the putrefaction of animal tissue. Cadaverine is a toxic[1] diamine with the formula NH2(CH2)5NH2, which is similar to putrescine. Cadaverine is also known by the names 1,5-pentanediamine and pentamethylenediamine. HistoryPutrescine[2] and cadaverine[3] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[4]ReceptorsIn zebrafish, the trace amine-associated receptor 13c (or TAAR13c) has been identified as a high-affinity receptor for cadaverin.[5] In humans, molecular modelling and docking experiments have shown that cadaverine fits into the binding pocket of the human TAAR6 and TAAR8.[6] ProductionCadaverine is the decarboxylation product of the amino acid lysine.[7] This can be done by heating lysine with a small amount of sodium bicarbonate mixed in. The produced gas should be led to a glass container which is surrounded by ice water. The heating must be done in a glass container, as metals may contaminate the process. However, this diamine is not purely associated with putrefaction. It is also produced in small quantities by living beings. It is partially responsible for the distinctive odors of urine and semen.[8] Clinical significanceElevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. The odor commonly associated with bacterial vaginosis has been linked to cadaverine and putrescine.[9] Derivatives
ToxicityCadaverine is toxic in large doses. In rats it has a low acute oral toxicity of 2,000 mg/kg body weight; its no-observed-adverse-effect level is 2,000 ppm (180 mg/kg body weight/day).[10] See also
References1. ^{{cite book | last =Lewis | first =Robert Alan | title =Lewis' Dictionary of Toxicology | publisher =CRC Press | year =1998 | isbn =1-56670-223-2 | page =212 }} 2. ^Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), [https://books.google.com/books?id=gqt9piJJ_TkC&pg=PA43&lpg=PA43&dq=putrescin&source=bl&ots=2TZTz8_are&sig=D6F9C-3IR1-7qkpsq_1poMwQFyU&hl=en&ei=26wQTMywPIO88gbguICCBg&sa=X&oi=book_result&ct=result&resnum=6&ved=0CCMQ6AEwBQ#v=onepage&f=false page 43]. 3. ^Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), [https://books.google.com/books?id=gqt9piJJ_TkC&pg=PA39&lpg=PA39&dq=cadaverin&source=bl&ots=2TZTz8_are&sig=D6F9C-3IR1-7qkpsq_1poMwQFyU&hl=en&ei=26wQTMywPIO88gbguICCBg&sa=X&oi=book_result&ct=result&resnum=6&ved=0CCMQ6AEwBQ#v=onepage&f=false page 39]. From page 39: Ich nenne das neue Diamin C5H16N2: "Cadaverin", da ausser der empirischen Zussamsetzung, welche die neue Base als ein Hydrür des Neuridins für den flüchtigen Blick erscheinen lässt, keine Anhaltspunkte für die Berechtigung dieser Auffassung zu erheben waren. (I call the new di-amine, C5H16N2, "cadaverine," since besides its empirical composition, which allows the new base to appear superficially as a hydride of neuridine, no clues for the justification of this view arose.) 4. ^Brief biography of Ludwig Brieger (in German). Biography of Ludwig Brieger in English. 5. ^{{cite journal|author=Li, Q|author2=Tachie-Baffour, Y|author3=Liu, Z|author4=Baldwin, MW|author5=Kruse, AC|author6=Liberles, SD|title=Non-classical amine recognition evolved in a large clade of olfactory receptors.|journal=eLife|year=2015|volume=4|pages=e10441|doi=10.7554/eLife.10441|pmid=26519734|url=https://elifesciences.org/articles/10441|pmc=4695389}} 6. ^{{cite journal|author=Izquierdo, C|author2=Gomez-Tamayo, JC|author3=Nebel, J-C|author4=Pardo, L|author5=Gonzalez, A|title=Identifying human diamine sensors for death related putrescine and cadaverine molecules.|journal=PLOS Computational Biology|year=2018|volume=14|issue=1|pages=e1005945|doi=10.1371/journal.pcbi.1005945|url=https://doi.org/10.1371/journal.pcbi.1005945}} 7. ^Wolfgang Legrum: Riechstoffe, zwischen Gestank und Duft, Vieweg + Teubner Verlag (2011) S. 65, {{ISBN|978-3-8348-1245-2}}. 8. ^[https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?q=all&cid=273#ec Cadaverine PubChem] 9. ^{{cite journal|author=Yeoman, CJ|author2=Thomas, SM|author3=Miller, ME|author4=Ulanov, AV|author5=Torralba, M|author6=Lucas, S|author7=Gillis, M|author8=Cregger, M|author9=Gomez, A|author10=Ho, M|author11=Leigh, SR|author12=Stumpf, R|author13=Creedon, DJ|author14=Smith, MA|author15=Weisbaum, JS|author16=Nelson, KE|author17=Wilson, BA|author18=White, BA|title=A multi-omic systems-based approach reveals metabolic markers of bacterial vaginosis and insight into the disease.|journal=PLOS ONE|year=2013|volume=8|issue=2|pages=e56111|doi=10.1371/journal.pone.0056111|pmid=23405259|url=http://www.plosone.org/article/info%3Adoi%2F10.1371%2Fjournal.pone.0056111|pmc=3566083}} 10. ^{{cite journal |last1=Til|first1=H.P.|last2=Falke|first2=H.E.|last3=Prinsen|first3=M.K.|last4=Willems|first4=M.I.|title=Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats|journal=Food and Chemical Toxicology |volume=35|issue=3-4|year=1997|pages=337–348|issn=0278-6915|doi=10.1016/S0278-6915(97)00121-X}} External links
2 : Diamines|Foul-smelling chemicals |
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