Spermine Chemical Properties

Melting point:

28-30 (lit.)

Boiling point:

150 °C/5 mmHg (lit.)

Density 

0.937

refractive index 

1.4850 (estimate)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

H₂O: 1 M at 20 °C, clear, colorless

form 

powder

pka

10.88±0.19(Predicted)

color 

Colorless to off-white

Water Solubility 

Soluble in chloroform, methanol, water and lower alcohols. Insoluble in ether, benzene and petroleum ether.

Sensitive 

Air Sensitive & Hygroscopic

Merck 

14,8743

BRN 

1751791

Stability:

Hygroscopic

InChIKey

PFNFFQXMRSDOHW-UHFFFAOYSA-N

LogP

-0.543 (est)

CAS DataBase Reference

71-44-3(CAS DataBase Reference)

NIST Chemistry Reference

Spermine(71-44-3)

EPA Substance Registry System

1,4-Butanediamine, N,N'-bis(3-aminopropyl)- (71-44-3)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/38-34

Safety Statements 

26-36-45-36/37/39-27

RIDADR 

UN 3259 8/PG 2

WGK Germany 

3

RTECS 

EJ7230000

F 

3-10

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29212900

MSDS

• Language:English Provider:SigmaAldrich

Spermine Usage And Synthesis

Description

Spermine is an endogenous polyamine synthesized from the reaction of spermidine with decarboxylated S-adenosylmethionine in the presence of the enzyme spermine synthase and is required for eukaryotic cell growth and protein synthesis. Intracellular spermine blocks inward rectifying K⁺ channels, whereas extracellular spermine acts as a mixed NMDA glutamate receptor agonist/antagonist at the polyamine site. Spermine has neuroprotective and anti-inflammatory effects and functions as a free radical scavenger to prevent DNA damage by reactive oxygen species.

Chemical Properties

White to slightly off-white powder crysta

Uses

immune modulator

Uses

Binds to the polyamine modulatory site of NMDA Spermine is essential for both normal and neoplastic tissue growth. It is involved in the modulation of calcium-dependent immune processes. It plays an important role in cellular proliferation and differentiation as well as inhibits neuronal nitric oxide synthase (nNOS).

Uses

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

Definition

ChEBI: A polyazaalkane that is tetradecane in which the carbons at positions 1, 5, 10 and 14 are replaced by nitrogens. Spermine has broad actions on cellular metabolism.

General Description

Spermine?is a polyamine, which functions as a free radical scavenger. It modulates gene expression, chromatin stabilization and prevents DNA damage. Spermine inhibits endonuclease-mediated DNA fragmentation.

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).

storage

+4°C (desiccate)

References

[1] fakler b, brndle u, glowatzki e, et al. strong voltage-dependent inward rectification of inward rectifier k+ channels is caused by intracellular spermine[j]. cell, 1995, 80(1): 149-154.
[2] til h p, falke h e, prinsen m k, et al. acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats[j]. food and chemical toxicology, 1997, 35(3): 337-348.

Spermine(71-44-3)Related Product Information

• Histamine
• Ethanethiol
• Diallylamine
• POLYAMINOPROPYL BIGUANIDE
• N,N-Diisopropylethylamine
• Diisopropylamine
• 1,4-DIAMINOBUTANE
• Spermidine
• Triallylamine
• Succinic acid
• Allylamine
• L(+)-Arginine
• O,O-Dimethyl phosphoramidothioate
• SPERMINE TETRAHYDROCHLORIDE
• SPERMINE TETRAHYDROCHLORIDE, [TERMINAL METHYLENE-3H]
• Spermine
• [14C]SPERMINE TETRAHYDROCHLORIDE