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85590

Sigma-Aldrich

Spermine

≥99.0% (GC)

Synonym(s):

N,N′-Bis(3-aminopropyl)-1,4-diaminobutane, Gerontine, Musculamine, Neuridine

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About This Item

Linear Formula:
NH2(CH2)3NH(CH2)4NH(CH2)3NH2
CAS Number:
71-44-3
Molecular Weight:
202.34
Beilstein/REAXYS Number:
1750791
EC Number:
200-754-2
MDL number:
MFCD00008215
UNSPSC Code:
12352116
PubChem Substance ID:
329769392
NACRES:
NA.25

biological source

microbial
synthetic

Quality Level

200

assay

≥99.0% (GC)

form

crystalline (chunks)

impurities

≤0.5% spermidine

bp

150 °C/5 mmHg (lit.)

mp

28-30 (lit.)

solubility

water: 0.05 g/mL, clear, colorless

anion traces

carbonate (CO32-): ≤5000 mg/kg

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

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Application

Spermine, a polycationic biogenic polyamine derived from spermidine, may be used in a wide variety of biological applications as a supplement or regulatory agent.Used as co-matrix with DHB for MALDI-MS of sialylated glycans in negative ion mode.

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).

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pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nicole K L Lee et al.
Journal of cellular physiology, 226(6), 1453-1460 (2011-03-18)
The naturally occurring polyamines, spermidine, spermine, and their precursor putrescine, play indispensible roles in both prokaryotic and eukaryotic cells, from basic DNA synthesis to regulation of cell proliferation and differentiation. The rate-limiting polyamine biosynthetic enzymes, ornithine decarboxylase (ODC) and S-adenosylmethionine
Y Mechref et al.
Journal of the American Society for Mass Spectrometry, 9(12), 1293-1302 (1998-12-03)
Negative-ion matrix-assisted laser desorption/ionization mass spectra of sialyated glycoconjugates were acquired employing 2,5-dihydroxybenzoic acid (DHB) in conjunction with spermine as a co-matrix. The addition of spermine to DHB permitted an improved crystal formation as well as a higher analyte solubility.
H Hosseinkhani et al.
Gene therapy, 11(2), 194-203 (2004-01-09)
Dextran-spermine cationic polysaccharide was prepared by means of reductive amination between oxidized dextran and the natural oligoamine spermine. The formed Schiff-base imine-based conjugate was reduced with borohydride to obtain the stable amine-based conjugate. The transfection efficiency of the synthetic dextran-spermine
Brian R Lee et al.
Nature neuroscience, 16(11), 1644-1651 (2013-10-01)
In rat models of drug relapse and craving, cue-induced cocaine seeking progressively increases after withdrawal from the drug. This 'incubation of cocaine craving' is partially mediated by time-dependent adaptations at glutamatergic synapses in nucleus accumbens (NAc). However, the circuit-level adaptations
Lydia P P Liew et al.
Bioorganic & medicinal chemistry letters, 23(2), 452-454 (2012-12-26)
Screening of synthesized and isolated marine natural products for in vitro activity against four parasitic protozoa has identified the ascidian metabolite 1,14-sperminedihomovanillamide (orthidine F, 1) as being a non-toxic, moderate growth inhibitor of Plasmodium falciparum (IC(50) 0.89 μM). Preliminary structure-activity
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