S3256

Spermine

≥97%

• Synonym(s): N,N′-Bis(3-aminopropyl)-1,4-diaminobutane, Gerontine, Musculamine, Neuridine
• Linear Formula: NH₂(CH₂)₃NH(CH₂)₄NH(CH₂)₃NH₂
• CAS Number: 71-44-3
• Molecular Weight: 202.34
• Beilstein: 1750791
• EC Number: 200-754-2
• MDL number: MFCD00008215
• UNSPSC Code: 12352116
• PubChem Substance ID: 24899550
• NACRES: NA.25

Properties

• biological source: microbial; synthetic
• description: form: solid or semisolid
• Assay: ≥97%
• bp: 150 °C/5 mmHg (lit.)
• mp: 28-30 (lit.)
• solubility: water: 50 mg/mL, clear, colorless
• storage temp.: 2-8°C
• SMILES string: [H]N(CCCN)CCCCN([H])CCCN
• InChI: 1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
• InChI key: PFNFFQXMRSDOHW-UHFFFAOYSA-N
• Gene Information: human ... GRIN2B(2904) ; rat ... Grin2a(24409)

Description

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.

Application

Spermine has been used:

• as an inositol 1,4,5-trisphosphate receptor (IP₃R)/glucose-regulated protein 75 (Grp75)/voltage-dependent anion channel 1 (VDAC1)/mitochondrial calcium uniporter (MCU) agonist to activate MCU in mouse podocytes
• in the biolistic transfection of filarial parasites
• for the production of adeno-associated virus (AAV)

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).

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H314
• Precautionary Statements: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Hazard Classifications: Eye Dam. 1 - Skin Corr. 1B
• Storage Class Code: 8A - Combustible corrosive hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves