(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine

• ChemBase编号: 13
• 分子式: C10H26N4
• 平均质量: 202.34024
• 单一同位素质量: 202.21574685
• SMILES: N(CCCCNCCCN)CCCN
• Canonical SMILES: NCCCNCCCCNCCCN
• InChI: InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
• InChIKey: PFNFFQXMRSDOHW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine
• IUPAC传统名: spermine
• 商标名: Gerontine; Musculamine; Neuridine
• 别名: N,N′-双(3-氨基丙基)-1,4-丁二胺; 精素; 肌胺; 肝胺; 精胺; N,N′-Bis(3-aminopropyl)-1,4-diaminobutane; Spermine; 1, 4-Bis(aminopropyl)butanediamine; 4,9-Diaza-1,12-dodecanediamine; 4,9-Diazadodecane-1,12-diamine; Spermin; Spermine dihydrate; Spermine; Gerontine; Musculamine; Neuridine; Diaminopropyltetramethylenediamine; N,N'-bis(aminopropyl)-1,4-butanediamine; N,N'-bis[3-Aminopropyl]-1,4-butanediamine; SPERMINE HCl; N,N’-Bis(3-aminopropyl)-1,4-butanediamine; N,N’-Bis(2-aminopropyl)tetramethylenediamine; NSC 268508

登记号

• CAS号: 305-67-2; 71-44-3
• EC号: 200-754-2
• MDL号: MFCD00008215
• Beilstein号: 1751791; 1750791
• 默克索引号: 148743
• PubChem SID: 160963476; 24899594; 46507215; 24899550
• PubChem CID: 1103
• CHEBI ID: 15746
• CHEMBL: 23194
• Chemspider ID: 1072
• DrugBank ID: DB00127
• Gmelin ID: 454653
• IUPHAR配体索引: 710
• KEGG ID: C00750
• 医学主题词(MeSH): Spermine
• 维基百科标题: Spermine

理论计算性质

JChem

• 质子受体: 4
• 质子供体: 4
• LogD (pH = 5.5): -13.23318
• LogD (pH = 7.4): -9.554461
• Log P: -1.4540076
• 摩尔折射率: 62.5582 cm^3
• 极化性: 25.284222 Å^3
• 极化表面积: 76.1 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.66
• LOG S: -1.97
• 溶解度: 2.19e+00 g/l

分子性质

理化性质

• 溶解度: > 100 mg/mL; Chloroform; H2O: soluble50 mg/mL; Methanol; Water
• 外观: amorphous semi-solid; Colourless crystals; White to Off-White Solid
• 熔点: 28 - 30°C; 28-30(lit.); 28-30°C; 53-58°C; 55-60°C
• 沸点: 141-142°C @ 0.5 mm Hg;; 150 °C/5 mmHg(lit.); 150.05°C (423.2K) (at 700 Pa); 150°C/5mm
• 闪点: >110°C(230°F); 110 °C; 110°C; 230 °F
• 密度: 937 mg mL^-1
• 分配系数: -0.543
• 疏水性(logP): -0.7
• 气味: Ichtyal, ammoniacal

安全信息

• 保存条件: 2-8°C, Desiccate, Store Under Nitrogen; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• 保存注意事项: Air Sensitive & Hygroscopic
• RTECS编号: EJ7175000
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• 联合国危险货物编号: 3259; 3263; UN3259
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; II; III
• 澳大利亚Hazchem: 2X
• 危险公开号: 34; R:34; r34
• 安全公开号: 20-26-36/37/39-45; 26-36/37/39-45; S:26-27/28-36/37/39-46-64; s26, s36/37/39, s45
• 欧盟危险货物分类: C8
• 欧盟危险识别号(EUHIN): 8B
• 美国ERG指导号: 154
• TSCA收录: 是
• GHS危险品标识: gHS corrosion; GHS05
• GHS警示词: DANGER; Danger
• GHS危险声明: 314; H314; H314-H318
• GHS警示性声明: 280, 305+351+338, 310; P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3259 8/PG 2
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... GRIN2B(2904)rat ... Grin2a(24409)

产品相关信息

• 纯度: ≥97%; ≥96%; ≥97%; 85-90%; 97%; 98%
• 适用性: suitable for cell culture
• 线性分子式: NH2(CH2)3NH(CH2)4NH(CH2)3NH2

详细说明

MP Biomedicals - 02152069

Free Base
Purity: 85-90%
Demonstrates activity similar to Spermidine.

MP Biomedicals - 02152070

Free Base
Purity: 97+%
This is a purified form of our Spermine. This is the highest purity spermine we've seen, and most others claim lower quality or make no claims about purity.

MP Biomedicals - 05207386

MP Biomedicals Rare Chemical collection

DrugBank - DB00127

• Drug Groups: approved; nutraceutical
• Description: A biogenic polyamine formed from spermidine. It is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at all pH values. Spermine is associated with nucleic acids, particularly in viruses, and is thought to stabilize the helical structure. [PubChem]
• Indication: For nutritional supplementation, also for treating dietary shortage or imbalance
• Pharmacology: Spermine is a polyamine. It is an organic molecule that is involved in cellular metabolism.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Sigma Aldrich - S4264

Biochem/physiol Actions
Spermine together with putrescine and spermidine compose a family of polyamines (polycations) that are required for the growth and survival of the vast majority of living cells. Polyamines interact with negatively charged molecules such as proteoglycans, glycated proteins and nucleic acids (DNA and RNA). Biogenic polyamines are found to modulate protein synthesis at different levels. This effect may be explained by the ability of polyamines to bind and influence the secondary structure of tRNA, mRNA, and rRNA. Spermine also helps stabilize nucleic acid helical structure and the conformation of glycated proteins such as the histones. Spermine and spermidine are components of various nucleic acid transfection protocols.Mixed NMDA glutamate receptor agonist/antagonist at the polyamine site. Neuroprotective effects have been observed at high concentrations (1 mM), while neurotoxicity is observed at lower concentrations. It enhances agonist effectiveness at the strychnine-insensitive glycine site. Plays a role in cellular proliferation and differentiation; inhibits neuronal nitric oxide synthase (nNOS).
多胺位点混合型 NMDA 谷氨酸受体激动剂/拮抗剂。在高浓度 (1mM) 下观察到神经保护作用，而在低浓度下则观察到神经毒性。它在番木鳖碱-不敏感性甘氨酸位点能够增强激动剂效应。在细胞增殖和分化中发挥作用；抑制神经元一氧化氮合成酶 (nNOS)。

Sigma Aldrich - S3256

包装
1, 5, 25 g in glass bottle
Biochem/physiol Actions
多胺位点混合型 NMDA 谷氨酸受体激动剂/拮抗剂。在高浓度 (1mM) 下观察到神经保护作用，而在低浓度下则观察到神经毒性。它在番木鳖碱-不敏感性甘氨酸位点能够增强激动剂效应。在细胞增殖和分化中发挥作用；抑制神经元一氧化氮合成酶 (nNOS)。

Sigma Aldrich - S3836

包装
1 g in glass bottle
Biochem/physiol Actions
多胺位点混合型 NMDA 谷氨酸受体激动剂/拮抗剂。在高浓度 (1mM) 下观察到神经保护作用，而在低浓度下则观察到神经毒性。它在番木鳖碱-不敏感性甘氨酸位点能够增强激动剂效应。在细胞增殖和分化中发挥作用；抑制神经元一氧化氮合成酶 (nNOS)。

Toronto Research Chemicals - S680510

Biogenic polyamine formed from spermidine and occurring in almost all tissues. Essential for both normal and neoplastic tissue growth. Involved in the modulation of calcium-dependent immune processes.

参考文献

• Israel, et al.: J. Med. Chem., 7, 710 (1964)
• Janne, J., et al.: Biochim. Biophys. Acta, 473, 241 (1978). Theoharides, T.C., et al.: Life Sci., 27, 703 (1964)
• Horn, Y., et al.: Cancer Res., 42, 3248 (1964)