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HomeProduct name listSpermine

Spermine

Synonym(s):N,N′-Bis(3-aminopropyl)-1,4-diaminobutane;Gerontine;Musculamine;Neuridine

  • CAS NO.:71-44-3
  • Empirical Formula: C10H26N4
  • Molecular Weight: 202.34
  • MDL number: MFCD00012914
  • EINECS: 200-754-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-20 11:41:24
Spermine Structural

What is Spermine?

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.

Description

The tetraamine spermine is biosynthesized from the triamine spermidine, which is produced from the diamine putrescine. Anton van Leeuwenhoek, the microscopy pioneer, described spermine crystals in human semen in 1678, and spermidine was also first detected in sperm. Despite their names, both polyamines are ubiquitous in organisms and have several biological functions.

Chemical properties

White to slightly off-white powder crysta

The Uses of Spermine

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).

The Uses of Spermine

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

The Uses of Spermine

immune modulator

What are the applications of Application

Spermine is a NOS1 inhibitor, NMDA activator, and GluR inhibitor

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.

Properties of Spermine

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
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 for Spermine

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
GHS Hazard Statements H314:Skin corrosion/irritation
H318:Serious eye damage/eye irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P310:Immediately call a POISON CENTER or doctor/physician.
P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for Spermine

InChIKey PFNFFQXMRSDOHW-UHFFFAOYSA-N

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