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

• ChemBase ID: 13
• Molecular Formular: C10H26N4
• Molecular Mass: 202.34024
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine
• IUPAC Traditional name: spermine
• Brand Name: Gerontine; Musculamine; Neuridine
• Synonyms: 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; N,N′-双(3-氨基丙基)-1,4-丁二胺; 精素; 肌胺; 肝胺; 精胺

Database IDs

• CAS Number: 71-44-3; 305-67-2
• EC Number: 200-754-2
• MDL Number: MFCD00008215
• Beilstein Number: 1751791; 1750791
• Merck Index: 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 ligand ID: 710
• KEGG ID: C00750
• MeSH Name: Spermine
• Wikipedia Title: Spermine

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -13.23318
• LogD (pH = 7.4): -9.554461
• Log P: -1.4540076
• Molar Refractivity: 62.5582 cm^3
• Polarizability: 25.284222 Å^3
• Polar Surface Area: 76.1 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.66
• LOG S: -1.97
• Solubility (Water): 2.19e+00 g/l

PROPERTIES

Physical Property

• Solubility: > 100 mg/mL; Chloroform; H2O: soluble50 mg/mL; Methanol; Water
• Apperance: amorphous semi-solid; Colourless crystals; White to Off-White Solid
• Melting Point: 28 - 30°C; 28-30(lit.); 28-30°C; 53-58°C; 55-60°C
• Boiling Point: 141-142°C @ 0.5 mm Hg;; 150 °C/5 mmHg(lit.); 150.05°C (423.2K) (at 700 Pa); 150°C/5mm
• Flash Point: >110°C(230°F); 110 °C; 110°C; 230 °F
• Density: 937 mg mL^-1
• Partition Coefficient: -0.543
• Hydrophobicity(logP): -0.7
• Odor: Ichtyal, ammoniacal

Safety Information

• Storage Condition: 2-8°C, Desiccate, Store Under Nitrogen; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Air Sensitive & Hygroscopic
• RTECS: EJ7175000
• European Hazard Symbols: Corrosive (C)
• UN Number: 3259; 3263; UN3259
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II; III
• Australian Hazchem: 2X
• Risk Statements: 34; R:34; r34
• Safety Statements: 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
• EU Classification: C8
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: gHS corrosion; GHS05
• GHS Signal Word: DANGER; Danger
• GHS Hazard statements: 314; H314; H314-H318
• GHS Precautionary statements: 280, 305+351+338, 310; P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: 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
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... GRIN2B(2904)rat ... Grin2a(24409)

Product Information

• Purity: ≥97%; ≥96%; ≥97%; 85-90%; 97%; 98%
• Suitability: suitable for cell culture
• Linear Formula: NH2(CH2)3NH(CH2)4NH(CH2)3NH2

DETAILS

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

Packaging
1 g in glass bottle
Biochem/physiol Actions
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).

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.

REFERENCES

• 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)