S2626

Spermidine

≥99% (GC)

• Synonym(s): 1,8-Diamino-4-azaoctane, N-(3-Aminopropyl)-1,4-diaminobutane
• Linear Formula: NH₂(CH₂)₃NH(CH₂)₄NH₂
• CAS Number: 124-20-9
• Molecular Weight: 145.25
• Beilstein: 1698591
• EC Number: 204-689-0
• MDL number: MFCD00008229
• UNSPSC Code: 12352200
• PubChem Substance ID: 24899529
• NACRES: NA.32

Properties

• biological source: synthetic
• Assay: ≥99% (GC)
• form: solid or liquid (clear)
• impurities: DNase, none detected; RNase, none detected; protease, none detected
• refractive index: n20/D 1.479 (lit.)
• mp: 22-25 °C
• solubility: water: 50 mg/mL, clear to very slightly hazy, colorless to very faintly yellow
• density: 0.925 g/mL at 25 °C (lit.)
• storage temp.: room temp
• SMILES string: NCCCCNCCCN
• InChI: 1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2
• InChI key: ATHGHQPFGPMSJY-UHFFFAOYSA-N
• Gene Information: rat ... Ppm1a(24666)

Description

General description

Spermidine, a natural biomolecule, is known for its wide-ranging health benefits, including anti-inflammatory effects, antioxidant properties, and improvements in respiratory function. It carries a positive charge at physiological pH, allowing it to interact with oppositely charged DNA and RNA. Dietary intake of spermidine is associated with a reduced risk of neurodegeneration, metabolic diseases, heart ailments, and cancer. Spermidine-induced autophagy has been shown to slow the rate of cognitive decline by clearing amyloid-beta plaques in the brain. Spermidine supplementation improves mitochondrial metabolism and translational activity. Moreover, spermidine exhibits cell-autonomous effects on cancer cells and influences their communication with immune effectors, leading to the acceleration of tumor-associated antigen identification and cancer cell death. Spermidine-mediated autophagy inhibits the activation of apoptosis in cancer cells and is linked to tissue development and cell differentiation. This natural compound is additionally recognized for its neuroprotective, and anti-aging properties and is naturally found in semen, as well as in various plant sources.

The enzyme nitric oxide synthase (nNOS) is involved in the production of nitric oxide.

Application

Spermidine has been used:

• in the preparation of 5x transcription buffer
• in the treatment of double-stranded RNA along with other reagents to increase the uptake of dsRNA by nematodes
• as a standard in the analytical study of rat brain polyamines (185)

Biochem/physiol Actions

Inhibits neuronal nitric oxide synthase (nNOS). Binds and precipitates DNA; may be used for purification of DNA binding proteins. Stimulates T₄ polynucleotide kinase activity.

Caution

Solutions should be sterile-filtered, not autoclaved, if sterile solution is necessary. Spermidine deaminates with time; solutions should be stored frozen. Prepare new solutions frequently.

Other Notes

Store under inert gas. Air sensitive; strongly hygroscopic.

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H314
• Precautionary Statements: P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363 - P405
• Hazard Classifications: Eye Dam. 1 - Skin Corr. 1B
• Storage Class Code: 8A - Combustible corrosive hazardous materials
• WGK: WGK 3
• Flash Point(F): 233.6 °F - closed cup
• Flash Point(C): 112 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves