这是用户在 2025-6-24 13:13 为 https://pubchem.ncbi.nlm.nih.gov/compound/273#section=MS-MS 保存的双语快照页面,由 沉浸式翻译 提供双语支持。了解如何保存?

美国政府官方网站

尸胺

PubChem CID
273
结构
尸胺_小.png
尸胺_3D_结构.png
尸胺__晶体结构.png
同义词
  • 戊烷-1,5-二胺
  • 1,5-二氨基戊烷
  • 尸胺
  • 462-94-2
  • 五亚甲基二胺
分子量
102.18 克/摩尔
由 PubChem 2.2 计算(PubChem 版本 2025.04.14)
日期
  • 创造
    2004年9月16日
  • 调整
    2025年6月21日
描述
尸胺是一种α,ω-烷烃二胺,由直链戊烷核心组成,在1位和5位上带有氨基取代基。它是一种无色糖浆状液体二胺,具有独特的难闻气味。它是腐胺的同系物,由赖氨酸在动物组织腐败过程中蛋白质水解过程中发生细菌脱羧而形成。它也存在于大豆等植物中。它既是植物代谢物,也是大型蚤的代谢物,也是大肠杆菌的代谢物,也是小鼠的代谢物。它是尸胺(2+)的共轭碱。
尸胺是赖氨酸经细菌脱羧反应生成的一种有恶臭味的二胺
尸胺是大肠杆菌(菌株K12,MG1655)中发现或产生的代谢物

1结构

1.1二维结构

化学结构描述
尸胺.png

1.2 3D 适形器

1.3晶体结构

2名称和标识符

2.1计算描述符

2.1.1 IUPAC名称

戊烷-1,5-二胺
由 Lexichem TK 2.7.0(PubChem 版本 2025.04.14)计算

2.1.2角蛋白

InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2
由 InChI 1.07.2 计算(PubChem 版本 2025.04.14)

2.1.3 InChIKey

VHRGRCVQAFMJIZ-UHFFFAOYSA-N
由 InChI 1.07.2 计算(PubChem 版本 2025.04.14)

2.1.4微笑

C(CCN)CCN
由 OEChem 2.3.0(PubChem 版本 2025.04.14)计算

2.2分子式

C5H14N2
由 PubChem 2.2 计算(PubChem 版本 2025.04.14)

2.3其他标识符

2.3.1 CAS

462-94-2

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 NCI Thesaurus Code

2.3.12 Nikkaji Number

2.3.13 Pharos Ligand ID

2.3.14 Wikidata

2.3.15 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1,5 Pentanediamine
  • 1,5-Pentanediamine
  • BioDex 1
  • Cadaverine
  • Pentamethylenediamine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

属性名称
Molecular Weight
Property Value
102.18 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2025.04.14)
Property Name
XLogP3-AA
Property Value
-0.6
Reference
Computed by XLogP3 3.0 (PubChem release 2025.04.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2025.04.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2025.04.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2025.04.14)
Property Name
Exact Mass
Property Value
102.115698455 Da
Reference
Computed by PubChem 2.2 (PubChem release 2025.04.14)
Property Name
单同位素质量
Property Value
102.115698455
Reference
由 PubChem 2.2 计算(PubChem 版本 2025.04.14)
Property Name
拓扑极面面积
Property Value
52 埃²
Reference
由 Cactvs 3.4.8.18 计算(PubChem 版本 2025.04.14)
Property Name
重原子计数
Property Value
7
Reference
由 PubChem 计算
Property Name
正式收费
Property Value
0
Reference
由 PubChem 计算
Property Name
复杂
Property Value
25.3
Reference
由 Cactvs 3.4.8.18 计算(PubChem 版本 2025.04.14)
Property Name
同位素原子计数
Property Value
0
Reference
由 PubChem 计算
Property Name
定义原子立体中心计数
Property Value
0
Reference
由 PubChem 计算
Property Name
未定义原子立体中心计数
Property Value
0
Reference
由 PubChem 计算
Property Name
定义键立构中心计数
Property Value
0
Reference
由 PubChem 计算
Property Name
未定义键立体中心计数
Property Value
0
Reference
由 PubChem 计算
Property Name
共价键合单元数
Property Value
1
Reference
由 PubChem 计算
Property Name
Compound 已规范化
Property Value
是的
Reference
由 PubChem 计算(版本 2025.04.14)

3.2实验性质

3.2.1物理描述

无色糖浆状液体,在空气中发烟;mp = 9 摄氏度;[默克指数]无色吸湿性液体,具有胺类气味;[Alfa Aesar MSDS]
液体

3.2.2颜色/形状

糖浆状无色液体
Lewis, RJ Sr.;《霍利简明化学词典》第15版。John Wiley & Sons, Inc. 纽约,2007年,第208页
浓稠发烟液体
Lewis, RJ Sr.(编)Sax著《工业材料的危险特性》。第11版。Wiley-Interscience出版社,Wiley & Sons公司,新泽西州霍博肯,2004年,第3版,第2843页。

3.2.3气味

特征气味
O'Neil, MJ (ed.). 默克索引 - 化学品、药物和生物制剂百科全书。新泽西州怀特豪斯站:默克公司,2006年,第262页
... 部分原因是尿液和精液的独特气味
欧洲化学 百科全书尸胺。自2011年4月13日起可从以下网址获取https://www.chemeurope.com/en/encyclopedia/cadaverine.html

3.2.4沸点

179 摄氏度
Lide, DR CRC《化学与物理手册》第88版 2007-2008. CRC Press, Taylor & Francis, Boca Raton, FL 2007, 第3-414页

3.2.5熔点

11.83 摄氏度
Lide, DR CRC《化学与物理手册》第88版 2007-2008. CRC Press, Taylor & Francis, Boca Raton, FL 2007, 第3-414页
9 摄氏度

3.2.6闪点

62 °C (144 °F) - 闭杯
Sigma-Aldrich;尸胺 材料 安全 数据 产品编号D22606。版本3.0 2008 年 8 月)。自2010 年10 月15 日,可从以下网址获取https://www.sigmaaldrich.com/safety-center/msds-search.html

3.2.7溶解度

溶于乙醇;微溶于乙醚
Lide, DR CRC《化学与物理手册》第88版 2007-2008. CRC Press, Taylor & Francis, Boca Raton, FL 2007, 第3-414页

3.2.8密度

25°C 时 0.873 克/立方厘米
Lide, DR CRC《化学与物理手册》第88版 2007-2008. CRC Press, Taylor & Francis, Boca Raton, FL 2007, 第3-414页

3.2.9蒸汽压

1.01 毫米汞柱

3.2.10稳定性/保质期

稳定。与酰氯、酸、酸酐、强氧化剂、二氧化碳不相容。
1,5-二氨基戊烷安全 数据(2005),自2010 年11 月19 日起可从以下网址获取https://msds.chem.ox.ac.uk/DI/1,5-diaminopentane.html

3.2.11分解

当加热分解时,它会释放出剧毒的/氮氧化物/烟雾。
Lewis, RJ Sr.(编)Sax著《工业材料的危险特性》。第11版。Wiley-Interscience出版社,Wiley & Sons, Inc.,新泽西州霍博肯,2004年,第2844页。

3.2.12 pH

强碱
O'Neil, MJ (ed.). 默克索引 - 化学品、药物和生物制剂百科全书。新泽西州怀特豪斯站:默克公司,2006年,第262页

3.2.13折射率

折射率 = 1.463(20 °C/D)
Lide, DR CRC《化学与物理手册》第88版 2007-2008. CRC Press, Taylor & Francis, Boca Raton, FL 2007, 第3-414页

3.2.14解离常数

pKa1 = 10.25;pKa2 = 9.13
O'Neil, MJ (ed.). 默克索引 - 化学品、药物和生物制剂百科全书。新泽西州怀特豪斯站:默克公司,2006年,第262页
8 件商品
pKa类型
pKaH1
酸碱度
10.25
温度[°C]
二十五
引文
A.杰罗. J. Am.化学。苏克。 76、5158、5159(1954 年)。
pKa类型
pKaH1
酸碱度
10.96
温度[°C]
20
引文
施瓦岑巴赫、B. 迈森和 H. 阿克曼。赫尔夫。奇姆。 Acta 35, 2333 (1952)。
pKa类型
pKaH1
酸碱度
10.916
温度[°C]
二十五
引文
R. Barbucci、P. Paoletti 和 A. Vacca。 J.化学。社会学会,A 1970,2202。
pKa类型
pKaH1
酸碱度
10.93
温度[°C]
二十五
引文
G.格尔巴德和P.伦普夫。公牛。苏克。奇姆。法国 1969 年、2120 年。
pKa类型
氢键pKa2
酸碱度
9.13
温度[°C]
二十五
引文
A.杰罗. J. Am.化学。苏克。 76、5158、5159(1954 年)。
2

3.2.15科瓦茨保留指数

标准非极性
1035,1035
标准极地
1537

3.2.16其他实验性质

暴露在空气中会产生烟雾并吸收二氧化碳
O'Neil, MJ (ed.). 默克索引 - 化学品、药物和生物制剂百科全书。新泽西州怀特豪斯站:默克公司,2006年,第262页
当加热分解时,它会释放出剧毒的 NOx 烟雾。
Lewis, RJ Sr.(编)Sax著《工业材料的危险特性》。第11版。Wiley-Interscience出版社,Wiley & Sons公司,新泽西州霍博肯,2004年,第3版,第2833页。
针状相,熔点225-230°C。可溶于。几乎不溶于无水乙醇。/尸胺二盐酸盐/
O'Neil, MJ (ed.). 默克索引 - 化学品、药物和生物制剂百科全书。新泽西州怀特豪斯站:默克公司,2006年,第262页

3.3 SpringerMaterials 属性

3.4化学类别

化合物 -> 脂肪族胺

3.4.1药物

制药 -> 列入 ZINC15
S55 | ZINC15PHARMA | ZINC15 药品|DOI:10.5281/zenodo.3247749

4光谱信息

4.1一维核磁共振谱

一维核磁共振谱

4.1.1 1H NMR 谱

1/5
查看全部
光谱识别
频率
600兆赫
溶剂
偏移量 [ppm]
1.49, 2.68, 1.35
缩略图
缩略图
光谱识别
仪器类型
布鲁克
频率
600兆赫
溶剂
pH
7.00
变化[ppm]:强度
1.35:25.12, 1.49:52.85, 1.36:9.65, 1.48:39.96, 1.33:12.08, 1.37:7.82, 1.52:12.71, 1.35:7.91, 2.67:69.64, 2.68:100.00, 1.34:7.86, 1.47:18.38, 2.69:66.51, 1.36:18.91, 1.32:3.88, 1.37:7.86, 1.32:3.87, 1.50:33.74
缩略图
缩略图

4.1.2 13C NMR 谱

1/4
查看全部
13C NMR光谱
13C NMR:144(Johnson 和 Jankowski,碳-13 NMR 谱,John Wiley & Sons,纽约)
光谱识别
仪器类型
瓦里安
频率
25.16兆赫
溶剂
氯化镉
变化[ppm]:强度
33.69:1000.00,24.20:559.00,42.14:935.00
缩略图
缩略图

4.1.3 15N NMR 谱

仪器名称
瓦里安DP-60
版权
版权所有 © 2002-2025 Wiley-VCH GmbH。保留所有权利。
缩略图
缩略图

4.2二维核磁共振谱

4.2.1 1H-13C NMR 谱

二维核磁共振谱类型
1H-13C HSQC
光谱识别
仪器类型
布鲁克
频率
600兆赫
溶剂
pH
7.00
偏移 [ppm] (F2:F1):强度
2.68:42.83:1.00,1.50:32.86:0.64,1.35:25.90:0.28
缩略图
缩略图

4.3质谱法

4.3.1气相色谱-质谱法

16 个中的1 个
查看全部
光谱识别
仪器类型
气相色谱-质谱法
五大山峰

174.0 1

175.0 0.31

86.0 0.29

176.0 0.16

100.0 0.15

缩略图
缩略图
16中的2
查看全部
光谱识别
仪器类型
EI-B
电离模式
积极的
五大山峰

174.15 100

175.2 16.53

86.05 8.63

176.15 7.40

375.3 7.29

缩略图
缩略图
笔记
仪器=GCMS-2010 Plus,岛津

4.3.2串联质谱

1/6
查看全部
光谱识别
仪器类型
Quattro_QQQ
电离模式
积极的
五大山峰

86.0 100

103.0 5.65

69.0 3.95

缩略图
缩略图
笔记
交付=Flow_Injectionanalyzer=Triple_Quad
6中的2
查看全部
光谱识别
仪器类型
Quattro_QQQ
电离模式
积极的
五大山峰

41.0 100

39.0 39.47

86.0 13.79

44.0 8.92

43.0 7.08

缩略图
缩略图
笔记
交付=Flow_Injectionanalyzer=Triple_Quad

4.3.3液相色谱-质谱联用

12 个中的1 个
查看全部
作者
Kakazu Y、Horai H,庆应义塾大学先进生物科学研究所
乐器
API3000,应用生物系统公司
仪器类型
液相色谱-电喷雾-QQ
硕士水平
MS2
电离模式
积极的
碰撞能量
10伏
母离子 m/z
103
前体加合物
[M+H]+
五大山峰

86.2 999

102.9 874

69.2 3

85.3 2

70.8 1

缩略图
缩略图
执照
共享创作署名-非商业性-相同方式共享
12中的2
查看全部
作者
Kakazu Y、Horai H,庆应义塾大学先进生物科学研究所
乐器
API3000,应用生物系统公司
仪器类型
液相色谱-电喷雾-QQ
硕士水平
MS2
电离模式
积极的
碰撞能量
20伏
母离子 m/z
103
前体加合物
[M+H]+
五大山峰

86.2 999

69 118

103.1 5

41.1 5

66.9 2

缩略图
缩略图
执照
共享创作署名-非商业性-相同方式共享

4.3.4其他质谱

1/5
查看全部
其他 MS
MASS:58609(NIST/EPA/ MSDC质谱数据库,1990年版)
作者
宫川 H、秋元 S、山崎 K、GL Sciences Inc.
乐器
岛津 GCMS-2010 Plus
仪器类型
EI-B
硕士水平
多发性硬化症
电离模式
积极的
列名称
InertCap 5MS/NP 0.25 毫米内径 x 30 米,df=0.25 微米
保留时间
755.7
五大山峰

174.15 999

175.2 165

86.05 86

176.15 74

375.3 73

缩略图
缩略图
执照
CC BY-SA

4.4红外光谱

4.4.1傅立叶变换红外光谱

技术
毛细管细胞:整洁
样本来源
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2025 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
缩略图

4.4.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
D22606
Copyright
Copyright © 2018-2025 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2025 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
缩略图

4.4.3 Near IR Spectra

Instrument Name
BRUKER IFS 88
Technique
NIR Spectrometer= INSTRUMENT PARAMETERS=INST=BRUKER,RSN=8951,REO=2,CNM=HEI,ZFF=2
Source of Spectrum
Prof. Buback, University of Goettingen, Germany
Copyright
Copyright © 1989, 1990-2025 Wiley-VCH GmbH. All Rights Reserved.
Thumbnail
缩略图

4.4.4 Vapor Phase IR Spectra

Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2025 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
缩略图

4.5 Raman Spectra

Copyright
Copyright © 2024-2025 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
缩略图

4.6 Other Spectra

1R: 6416 (Coblentz Society spectral collection)
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V4: 3839

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Absorption, Distribution and Excretion

The urinary excretion of histamine, methylhistamine, putrescine, cadaverine, spermidine and spermine was examined before, during and after pregnancy in rats. During the last third of undisturbed pregnancy a distinct and steep rise occurred in the excretion of all amines studied except spermine. The peak values were found a few days before the birth of the young. In spermidine excretion a second peak was observed one or two days after delivery. Before and during the first 2 weeks of gestation on a molar basis putrescine excretion was the greatest one. During the last trimester histamine was excreted in the largest amount. Under the influence of the diamine oxidase inhibitor aminoguanidine the general pattern of excretion of diamines and polyamines in pregnant rats remained essentially unchanged but the total amount excreted increased. Most conspicuous was the great elevation of urinary contents of putrescine and cadaverine.
Andersson AC et al; J Physiol 285: 311-24 (1978)
Cadaverine has been shown to be present in the central nervous system (CNS) ... Its concentration in the whole brain varies during behavioral sleep in mammals and during hibernation in molluscs. ... Cadaverine has been considered a non-metabolite of the brain, and its presence in the body was believed to be due almost entirely to bacterial decarboxylation of lysine in the intestine. In slices of mouse brain, exogenous cadaverine accumulates against a concentration gradient and can reach a concentration ten times greater in the tissue than in the surrounding medium. The question has been therefore: does the cadaverine in the brain originate from an exogenous source; is it formed and resorbed in the intestine? Assaying cadaverine in axenic mice, /it has been/ found that this is not the case, and that there is an endogenous source of cadaverine in the mouse.
Matej S-K, Dolezalova H; Nature 252: 158-9 (1974)

7.2 Metabolism / Metabolites

It is a precursor of piperidine, which has been linked with some functional stages of the CNS. Cadaverine is the source of much of the piperidine excreted in the urine.
Matej S-K, Dolezalova H; Nature 252: 158-9 (1974)
Cadaverine ... a relatively nontoxic ptomaine, C5H14N2, formed by decarboxylation of lysine; it is sometimes one of the products of Vibrio proteus and of V. cholerae, and occasionally found in the urine in cystinuria, where it causes an unpleasant odor.
Merck Source; Resource Library Powered by Dorland's Medical Dictionary for Healthcare Consumers. Available from, as of November 19, 2010: https://www.mercksource.com/pp/us/cns/cns_hl_dorlands_split.jsp?pg=/ppdocs/us/common/dorlands/dorland/misc/dmd-a-b-000.htm
Cadaverine is synthesized from lysine in a one-step reaction with lysine decarboxylase (LDC).
ChemEurope.com; Polyamine. In Encyclopedia of Chemistry. Available from, as of November 19, 2010: https://www.chemeurope.com/lexikon/e/Polyamine/

7.3 Human Metabolite Information

7.3.1 Tissue Locations

  • Epidermis
  • Intestine
  • Prostate

7.3.2 Cellular Locations

Cytoplasm

7.4 Biochemical Reactions

8 Use and Manufacturing

8.1 Uses

Sources/Uses
A foul-smelling diamine formed by bacterial decarboxylation of lysine. [ChemIDplus] Biogenic polyamine present in cholera discharge; [Merck Index] Formed from decay of animal proteins; Used to make high polymers, as an intermediate, and in biological research; [HSDB]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
Preparation of high polymers, intermediate, biological research.
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 208

8.2 Methods of Manufacturing

... 1,5-Diaminopentane can be produced from/ the starting materials 1,5-dichloropentane (obtainable from tetrahydropyran), glutarodinitrile, or glutaraldehyde (e.g., Relugan, BASF).
Eller K et al; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (2008). New York, NY: John Wiley & Sons; Amines, Aliphatic. Online Posting Date: 15 Jun 2000.

8.3 General Manufacturing Information

EPA TSCA Commercial Activity Status
1,5-Pentanediamine: ACTIVE
A ptomaine formed in the decay of animal proteins after death
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 208
... also made synthetically
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 208
Biogenic amines are non-volatile amines formed by decarboxylation of amino acids. Although many biogenic amines have been found in fish, only histamine, cadaverine, and putrescine have been found to be significant in fish safety and quality determination. Despite a widely reported association between histamine and scombroid food poisoning, histamine alone appears to be insufficient to cause food toxicity. Putrescine and cadaverine have been suggested to potentiate histamine toxicity. With respect to spoilage on the other hand, only cadaverine has been found to be a useful index of the initial stage of fish decomposition ...
Al Bulushi I et al; Crit Rev Food Sci Nutr 49 (4): 369-77 (2009)
Cadaverine - A syrupy, colorless, fuming ptomaine formed by the carboxylation of lysine by bacteria in decaying animal flesh.
The American Heritage Medical Dictionary, Houghton Mifflin Company (2004)
For more General Manufacturing Information (Complete) data for Cadaverine (6 total), please visit the HSDB record page.

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
腐蚀性
刺激性
Signal
Danger
GHS Hazard Statements

H302+H312 (64.2%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]

H302 (68.5%): Harmful if swallowed [Warning Acute toxicity, oral]

H312 (71%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

H318 (70.4%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statement Codes

P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 162 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

9.1.2 Hazard Classes and Categories

Acute Tox. 4 (68.5%)

Acute Tox. 4 (71%)

Skin Corr. 1B (100%)

Eye Dam. 1 (70.4%)

9.1.3 NFPA Hazard Classification

NFPA 704 Diamond
3-2-0
NFPA Health Rating
3 - Materials that, under emergency conditions, can cause serious or permanent injury.
NFPA Fire Rating
2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.
NFPA Instability Rating
0 - Materials that in themselves are normally stable, even under fire conditions.

9.1.4 Hazards Summary

A strong base that attracts carbon dioxide; A skin irritant and possible sensitizer; [Merck Index] Causes burns; [HSDB] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Alfa Aesar MSDS] Search for (462-94-2[EC/RN Number]) AND (sensitizer OR sensitization OR allergic OR dermatitis): no papers confirming skin sensitization; [PubMed] See 1,6-Diaminohexane.
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.

9.1.5 Fire Potential

Combustible liquid
Sigma-Aldrich; Material Safety Data Sheet for Cadaverine. Product Number D22606. Version 3.0 (August 2008). Available from, as of October 15, 2010: https://www.sigmaaldrich.com/safety-center/msds-search.html

9.1.6 Skin, Eye, and Respiratory Irritations

An irritant ...
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2844

9.2 Fire Fighting

9.2.1 Fire Fighting Procedures

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self contained breathing apparatus for fire fighting if necessary.
Sigma-Aldrich; Material Safety Data Sheet for Cadaverine. Product Number D22606. Version 3.0 (August 2008). Available from, as of October 15, 2010: https://www.sigmaaldrich.com/safety-center/msds-search.html

9.3 Accidental Release Measures

9.3.1 Cleanup Methods

Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal. Do not let product enter drains.
Sigma-Aldrich; Material Safety Data Sheet for Cadaverine. Product Number D22606. Version 3.0 (August 2008). Available from, as of October 15, 2010: https://www.sigmaaldrich.com/safety-center/msds-search.html

9.3.2 Disposal Methods

This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: dispose of as unused product.
Sigma-Aldrich; Material Safety Data Sheet for Cadaverine. Product Number D22606. Version 3.0 (August 2008). Available from, as of October 15, 2010: https://www.sigmaaldrich.com/safety-center/msds-search.html

9.3.3 Preventive Measures

Avoid inhalation of vapour or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.
Sigma-Aldrich; Material Safety Data Sheet for Cadaverine. Product Number D22606. Version 3.0 (August 2008). Available from, as of October 15, 2010: https://www.sigmaaldrich.com/safety-center/msds-search.html
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

9.4 Handling and Storage

9.4.1 Storage Conditions

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Store under inert gas.
Sigma-Aldrich; Material Safety Data Sheet for Cadaverine. Product Number D22606. Version 3.0 (August 2008). Available from, as of October 15, 2010: https://www.sigmaaldrich.com/safety-center/msds-search.html

9.5 Exposure Control and Personal Protection

9.5.1 Personal Protective Equipment (PPE)

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Hand protection: Handle with gloves. Eye protection: Safety glasses Skin and body protection: Choose body protection according to the amount and concentration of the dangerous substance at the work place.
Sigma-Aldrich; Material Safety Data Sheet for Cadaverine. Product Number D22606. Version 3.0 (August 2008). Available from, as of October 15, 2010: https://www.sigmaaldrich.com/safety-center/msds-search.html
Safety glasses, good ventilation, gloves
Safety data for 1,5-diaminopentane (2005), Available from, as of November 19, 2010: https://msds.chem.ox.ac.uk/DI/1,5-diaminopentane.html

9.6 Stability and Reactivity

9.6.1 Hazardous Reactivities and Incompatibilities

Materials to avoid Acid chlorides, Acid anhydrides, acids, Strong oxidizing agents, Carbon dioxide (CO2)
Sigma-Aldrich; Material Safety Data Sheet for Cadaverine. Product Number D22606. Version 3.0 (August 2008). Available from, as of October 15, 2010: https://www.sigmaaldrich.com/safety-center/msds-search.html

9.7 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 1,5-Pentanediamine
EPA TSCA Regulatory Flag
PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
1,5-Pentanediamine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

9.8 Other Safety Information

Chemical Assessment
Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment

9.8.1 Toxic Combustion Products

Hazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx)
Sigma-Aldrich; Material Safety Data Sheet for Cadaverine. Product Number D22606. Version 3.0 (August 2008). Available from, as of October 15, 2010: https://www.sigmaaldrich.com/safety-center/msds-search.html

10 Toxicity

10.1 Toxicological Information

10.1.1 Toxicity Summary

IDENTIFICATION AND USE: Cadaverine is a syrupy, colorless liquid with a distinctive odor of urine and semen. It is soluble in water, ethanol; slightly soluble in ethyl ether, and miscible in water. It is used in the production of high polymers, as a chemical intermediate, and in biological research. HUMAN EXPOSURE AND TOXICITY: It is a foul-smelling diamine formed by bacterial decarboxylation of lysine. It is poisonous and irritating to the skin. Harmful if ingested, inhaled, or absorbed through the skin. It can cause burns and is very destructive of mucous membranes. Occupational exposure to cadaverine may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used. Monitoring data indicate that the general population may be exposed to cadaverine by ingestion of certain meats. ANIMAL STUDIES: In In rats, cadaverine had a low oral toxicity. Cadaverine caused a dose-related decrease in blood pressure after intravenous administration in rats. The subacute toxicity of this chemical was examined in rats. Cadaverine was administered in the diet to groups of 10 male and 10 female rats. Adverse effects were observed in the high dose group and decreased body weights associated with diminished food intake were observed. Slight increases in packed cell volume, hemoglobin concentration, and thrombocytes occurred with chemical exposure.

10.1.2 Adverse Effects

Dermatotoxin - Skin burns.

Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

10.1.3 Acute Effects

10.1.4 Interactions

Histamine poisoning can result from the ingestion of food containing unusually high levels of histamine. ... Histamine poisoning is characterized by a short incubation period, a short duration, and symptoms resembling those associated with allergic reactions. The evidence supporting the role of histamine as the causative agent is compelling. ... Histamine ingested with spoiled fish appears to be much more toxic than histamine ingested in an aqueous solution. The presence of potentiators of histamine toxicity in the spoiled fish may account for this difference in toxicity. Several potentiators including other putrefactive amines such as putrescine and cadaverine have been identified. Pharmacologic potentiators may also exist; aminoguanidine and isoniazid are examples. The mechanism of action of these potentiators appears to be the inhibition of intestinal histamine-metabolizing enzymes. This enzyme inhibition causes a decrease in histamine detoxification in the intestinal mucosa and results in increased intestinal uptake and urinary excretion of unmetabolized histamine.
Taylor SL; Crit Rev Toxicol 17 (2): 91-128 (1986)

10.1.5 Antidote and Emergency Treatment

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160-1

10.1.6 Human Toxicity Excerpts

/SIGNS AND SYMPTOMS/ Cadaverine ... a foul-smelling diamine formed by bacterial decarboxylation of lysine. It is poisonous and irritating to the skin.
Mosby's Dental Dictionary, 2nd edition. Elsevier, Inc (2008)
/SIGNS AND SYMPTOMS/ Stench! Harmful if ingested, inhaled, or absorbed through the skin. Corrosive - causes burns. Very destructive of mucous membranes.
Safety data for 1,5-diaminopentane (2005), Available from, as of November 19, 2010: https://msds.chem.ox.ac.uk/DI/1,5-diaminopentane.html

10.1.7 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ The acute ... toxicity of ... cadaverine /was/ examined in Wistar rats. ... Cadaverine had a low acute oral toxicity of more than 2000 mg/kg body weight. /Cadaverine/ ... caused a dose-related decrease in blood pressure after intravenous administration ...
Til HP et al; Food Chem Toxicol 35 (3-4): 337-48 (1997)
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... This study was designed to determine if biogenic amines, at the concentrations found in animal by-product meals, would reduce performance in broilers or cause lesions. Twelve treatments were used in a 2 x 6 factorial arrangement with the main effects being either a corn-soybean meal diet or a corn-soybean meal diet with 10% animal by-products added and either no amines added or added levels of phenylethylamine (4.8 mg/kg), putrescine (49 mg/kg), cadaverine (107 mg/kg), histamine (131 mg/kg), or a combination of all these amines. Levels of biogenic amines used in this study simulated those found in areas with reported problems attributed to biogenic amines. Broilers were monitored for performance, gross lesions, and histologic evidence of lesions at 2, 4, and 6 wk. No consistent effects were observed on performance, and by the conclusion of the trial, no statistical differences were noted in the performance of any of the treatments. No gross lesions were observed on a consistent basis in any of the treatments. Histopathology was likewise unremarkable. On the basis of this study, it would appear that these four biogenic amines, at levels detected in the United States, do not pose a serious health concern for the broiler industry.
Bermudez AJ, Firman JD; Avian Dis 42 (1): 100=203 (1998)
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The ... subacute toxicity of ... cadaverine /was/ examined in Wistar rats. ... In 6-wk studies ... /cadaverine was/ administered in the diet to groups of 10 male and 10 female rats ... at levels of 0, 200, 2000 or 5000 ppm ... in the first study and at levels of 0 or 10,000 ppm in a second study. ... Adverse effects were ... observed in the top dose group ... Decreased body weights associated with diminished food intake were ... seen. Slight increases in packed cell volume, hemoglobin concentration and thrombocytes occurred with cadaverine. ... The no-observed-adverse-effect level was 2000 ppm (180 mg/kg body weight/day) for ... cadaverine ...
Til HP et al; Food Chem Toxicol 35 (3-4): 337-48 (1997)
/ALTERNATIVE and IN VITRO TESTS/ Effects of polyamines (0.05-1.2 mM) on the mechanical and electrical activities in the circular muscles of pre-(day 20 of pregnancy) and post-partum (10-15 hr after delivery) rat myometria were studied. In the prepartum preparations, spermine and spermidine, added to the Mg-free Krebs solution, depressed contractions in a dose-dependent manner, whereas cadaverine and putrescine potentiated them. The latter agents depressed contractions when preparations were treated with indomethacin. Plateau potentials were spontaneously generated in the Mg-free solution in the prepartum circular muscle. The duration of the plateau became shorter, and spike potentials supermounted on the plateau potential were depressed when spermine or spermidine was applied. In the postpartum preparations, spike activity was depressed by spermine and spermidine. In both pre- and post-partum preparations, the membrane activity was little affected by cadaverine and putrescine. In view of the above findings, it was hypothesized that polyamines in general took the place of divalent cations in causing membrane stabilization. Cadaverine and putrescine probably caused a potentiation of contraction by stimulating the synthesis of endogenous prostaglandins.
Maruta K et al; Jpn J Physiol 35 (6): 903-15 (1985)
/OTHER TOXICITY INFORMATION/ In the testosterone-induced hypertrophic and antifolate (N10-propargyl,5,6-dideazafolic acid, CB 3717)-induced hyperplastic mouse kidney models, a marked increase of two diamine levels--putrescine and cadaverine--occurred which paralleled induced ornithine decarboxylase (ODC) activity. Under these conditions the augmentation of spermidine levels was much smaller, while spermine levels were affected differentially--increased by testosterone and decreased by CB 3717; this resulted in an increase of spermidine/spermine ratio in hyperplastic, but not hypertrophic kidney ...
Manteuffel-Cymborowska M et al; Biochim Biophys Acta 1182 (2): 133-41 (1993)

10.2 Ecological Information

10.2.1 Ecotoxicity Values

LD50; Species: Peromyscus maniculatus (Deer Mouse) oral 1600 mg/kg
Schafer EW Jr., Bowles WA Jr.; Arch Environ Contam Toxicol 14 (1): 111-29 (1985) as cited in the ECOTOX database. Available from, as of November 2, 2010
USDA APHIS Chemical Effects
Schafer, E. W., Jr., and W. A. Bowles Jr. 1985. Acute oral toxicity and repellency of 933 chemicals to house and deer mice. Archives of Environmental Contamination and Toxicology 14:111-129. https://www.aphis.usda.gov/ws/nwrc/chem-effects-db/S_schafer851.pdf
Schafer, E. W., Jr., W. A. Bowles Jr., and J. Hurlbut. 1983. The acute oral toxicity and repellency and hazard potential of 998 chemicals to one or more species of wild and domestic birds. Archives of Environmental Contamination and Toxicology 12:355-382. https://www.aphis.usda.gov/ws/nwrc/chem-effects-db/Q_schafer832.pdf

10.2.2 Environmental Fate / Exposure Summary

Cadaverine's production and use as a chemical intermediate and in biological research may result in its release to the environment through various waste streams. It is formed in the decay of animal proteins after death and also produced in small quantities by living beings. If released to air, an estimated vapor pressure of 1.0 mm Hg at 25 °C indicates cadaverine will exist solely as a vapor in the atmosphere. Vapor-phase cadaverine will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 6 hours. Cadaverine does not contain chromophores that absorb at wavelengths >290 nm, and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, cadaverine is expected to have high mobility based upon an estimated Koc of 90. However, the pKa values of cadaverine are 9.13 and 10.25, indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization from moist soil is not expected because the compound exists as a cation and cations do not volatilize. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.4X10-9 atm-cu m/mole. Biodegradation data were not available. If released into water, cadaverine is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. The pKa values indicate cadaverine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is expected to be an important environmental fate process since this compound contains functional groups that hydrolyze under environmental conditions. Occupational exposure to cadaverine may occur through inhalation and dermal contact with this compound at workplaces where cadaverine is produced or used. Monitoring data indicate that the general population may be exposed to cadaverine via ingestion of certain meats. (SRC)

10.2.3 Natural Pollution Sources

Cadaverine is a ptomaine formed in the decay of animal proteins after death(1). It is also produced in small quantities by living beings and is partially responsible for the distinctive smell of urine and semen(2). It is related to putrescine. Both are produced by the breakdown of amino acids in living and dead organisms(3).
(1) Lewis RJ Sr; Hawley's Condensed Chemical Dictionary. 15th ed. New York, NY: John Wiley & Sons, Inc., p. 208 (2007)
(2) ChemEurope; Encyclopedia of Chemistry. Cadaverine. Available from, as of April 13, 2011: https://www.chemeurope.com/en/encyclopedia/cadaverine.html
(3) ChemEurope; Encyclopedia of Chemistry. Putrescine. Available from, as of April 13, 2011: https://www.chemeurope.com/en/encyclopedia/Putrescine.html

10.2.4 Artificial Pollution Sources

Cadaverine's production and use as a chemical intermediate and in biological research(1) may result in its release to the environment through various waste streams(SRC).
(1) Lewis RJ Sr; Hawley's Condensed Chemical Dictionary. 15th ed. New York, NY: John Wiley & Sons, Inc., p. 208 (2007)

10.2.5 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 90(SRC), determined from a structure estimation method(2), indicates that cadaverine is expected to have high mobility in soil(SRC). However, the pKa values of cadaverine are 9.13 and 10.25(3), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as a cation and cations do not volatilize. Cadaverine is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.0 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Biodegradation data in soil were not available(SRC, 2010).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) O'Neil MJ, ed, The Merck Index. 14 th ed., Whitehouse Station, NJ: Merck and Co., Inc., p. 262 (2006)
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
(5) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 90(SRC), determined from a structure estimation method(2), indicates that cadaverine is not expected to adsorb to suspended solids and sediment(SRC). The pKa values of 9.13 and 10.25(3) indicate cadaverine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of -0.15(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2010).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) O'Neil MJ, ed, The Merck Index. 14 th ed., Whitehouse Station, NJ: Merck and Co., Inc., p. 262 (2006)
(4) Franke C et al; Chemosphere 29: 1501-14 (1994)
(5) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(6) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.0. Jan, 2009. Available from, as of Oct 7, 2010: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cadaverine, which has a /an estimated vapor pressure of 1.0 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cadaverine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 6 hours(SRC), calculated from its rate constant of 6.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Cadaverine does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12 (1990)

10.2.6 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of cadaverine with photochemically-produced hydroxyl radicals has been estimated as 6.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Cadaverine may be expected to undergo hydrolysis in the environment due to the presence of functional groups that hydrolyze under environmental conditions(2). Cadaverine does not contain chromophores that absorb at wavelengths >290 nm(2), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12 (1990)

10.2.7 Environmental Bioconcentration

An estimated BCF of 3 was calculated in fish for cadaverine(SRC), using an estimated log Kow of -0.15(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
(1) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.0. Jan, 2009. Available from, as of Oct 7, 2010: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

10.2.8 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc of cadaverine can be estimated to be 90(SRC). According to a classification scheme(2), this estimated Koc value suggests that cadaverine is expected to have high mobility in soil. However, the pKa values of cadaverine are 9.13 and 10.25(3), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
(1) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(2) Swann RL et al; Res Rev 85: 17-28 (1983)
(3) O'Neil MJ, ed, The Merck Index. 14 th ed., Whitehouse Station, NJ: Merck and Co., Inc., p. 262 (2006)
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)

10.2.9 Volatilization from Water / Soil

The pKa values of 9.13 and 10.25(3) indicate cadaverine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water and moist soil surfaces is not expected to be an important fate process. Cadaverine is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.0 mm Hg(SRC), determined from a fragment constant method(2).
(1) O'Neil MJ, ed, The Merck Index. 14 th ed., Whitehouse Station, NJ: Merck and Co., Inc., p. 262 (2006)
(2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)

10.2.10 Effluent Concentrations

Cadaverine was tested for but not detected in gasoline nor diesel exhaust(1).
(1) Westerholm R et al; Chemosphere 27: 1381-84 (1993)

10.2.11 Food Survey Values

Cadaverine levels in fresh pork and beef meat were not detected to 0.7 mg/kg and not detected, respectively. Levels in cooked ham and mortadella were not detected to 0.9 mg/kg and not detected to 7.9 mg/kg, respectively. The cadaverine content in ripened meat products ranged from 3.9 to 34.9 mg/kg chorizo and 2.1 to 68.5 mg/kg in salchichon(1).
(1) Hernandez-Jover T et al; J Agric Food Chem 44: 2710-2715 (1996)

10.2.12 Plant Concentrations

Cadaverine was detected, not quantified in unspecified freshwater and marine algae(1).
(1) Kneifel H et al; J Phycol 13: 36 (1977)

10.2.13 Probable Routes of Human Exposure

Occupational exposure to cadaverine may occur through inhalation and dermal contact with this compound at workplaces where cadaverine is produced or used. Monitoring data indicate that the general population may be exposed to cadaverine via ingestion of certain meats. (SRC)

11 Associated Disorders and Diseases

Disease
Kidney disease
References
Disease
Irritable bowel syndrome
References
Disease
Colorectal cancer
References

PubMed: 7482520, 19006102, 23940645, 24424155, 20156336, 19678709, 22148915, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

Disease
Perillyl alcohol administration for cancer treatment
References
Disease
Pancreatic cancer
References
Disease
Periodontal disease
References
PubMed: 20300169
Disease
Thyroid cancer
References
Disease
Leukemia
References

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Wiley References

12.6 Chemical Co-Occurrences in Literature

12.7 Chemical-Gene Co-Occurrences in Literature

12.8 Chemical-Disease Co-Occurrences in Literature

12.9 Chemical-Organism Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

13.6 Chemical-Organism Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Protein Bound 3D Structures

14.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

14.2 Chemical-Target Interactions

14.3 Pathways

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 ChEBI Ontology

17.4 ChemIDplus

17.5 ChEMBL Target Tree

17.6 UN GHS Classification

17.7 NORMAN Suspect List Exchange Classification

17.8 EPA DSSTox Classification

17.9 EPA TSCA and CDR Classification

17.10 LOTUS Tree

17.11 EPA Substance Registry Services Tree

17.12 MolGenie Organic Chemistry Ontology

17.13 Chemicals in PubChem from Regulatory Sources

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/chemidplus
  4. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  5. EPA Chemicals under the TSCA
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  8. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  9. Hazardous Substances Data Bank (HSDB)
  10. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  11. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  12. USDA APHIS Chemical Effects Database
  13. ChEBI
  14. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  15. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  16. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  17. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  18. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  19. Therapeutic Target Database (TTD)
  20. KNApSAcK Species-Metabolite Database
  21. Natural Product Activity and Species Source (NPASS)
  22. West Coast Metabolomics Center-UC Davis
    1,5-Pentanediamine
  23. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  24. IUPAC Digitized pKa Dataset
  25. MassBank Europe
  26. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  27. SpectraBase
  28. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  29. Japan Chemical Substance Dictionary (Nikkaji)
  30. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  31. Metabolomics Workbench
  32. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  33. NMRShiftDB
  34. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Cadaverine
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  35. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  36. Protein Data Bank in Europe (PDBe)
  37. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  38. Springer Nature
  39. SpringerMaterials
  40. The Cambridge Structural Database
  41. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  42. Wikidata
  43. Wikipedia
  44. Wiley
  45. Medical Subject Headings (MeSH)
    LICENSE
    美国政府制作的作品在美国不受版权保护。在美国国家医学图书馆 (NLM) 网站上找到的任何此类作品均可在美国自由使用或复制,无需许可。
    https://www.nlm.nih.gov/copyright.html
  46. PubChem
  47. GHS分类(联合国欧洲经济委员会)
  48. EPA物质注册服务
    EPA SRS 清单分类
    https://maldi.nist.gov
  49. MolGenie
    MolGenie有机化学本体
    https://github.com/MolGenie/ontology/
  50. 专利范围(WIPO)
  51. 国家生物技术信息中心
内容
原文
请对此翻译评分
您的反馈将用于改进谷歌翻译