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Spermidine

Spermidine
Skeletal formula of spermidine
Ball and stick model of spermidine
Identifiers
124-20-9 YesY
3D model (Jmol) Interactive image
3DMet B01214
1698591
ChEBI CHEBI:16610 N
ChEMBL ChEMBL19612 N
ChemSpider 1071 N
DrugBank DB03566 YesY
ECHA InfoCard 100.004.264
EC Number 204-689-0
454510
2390
KEGG C00315 N
MeSH Spermidine
PubChem 1102
RTECS number EJ7000000
UN number 2735
Properties
C7H19N3
Molar mass 145.25 g·mol−1
Appearance Colourless liquid
Odor Ichtyal, ammoniacal
Density 925 mg mL−1
Melting point 22 to 25 °C (72 to 77 °F; 295 to 298 K)
145 g L−1 (at 20 °C)
log P −0.504
UV-vismax) 260 nm
Absorbance 0.1
1.479
Hazards
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H314
P280, P305+351+338, P310
Corrosive C
R-phrases R34
S-phrases S26, S36/37/39
Flash point 112 °C (234 °F; 385 K)
Related compounds
Related amines
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Spermidine is a polyamine compound (C
7
H
19
N
3
) found in ribosomes and living tissues, and having various metabolic functions within organisms. It was originally isolated from semen.

Polyamines, such as spermidine, are polycationic aliphatic amines and are multifunctional. They serve vital roles in cell survival.

Spermidine synthase (SPDS) catalyzes the formation of spermidine from putrescine. Spermidine is a precursor to further polyamines, such as spermine and its structural isomer thermospermine.

Spermidine synchronizes an array of biological processes (such as Ca2+, Na+, K+ -ATPase) thus maintaining membrane potential and controlling intracellular pH and volume. Spermidine regulates biological processes, such as Ca2+ influx by glutamatergic N-methyl-d-aspartate receptor (NMDA receptor), which has been associated with nitric oxide synthase (NOS) and cGMP/PKG pathway activation and a decrease of Na+,K+-ATPase activity in cerebral cortex synaptosomes.

Spermidine is a longevity agent in mammals due to various mechanisms of action, which are just beginning to be understood. Autophagy is the main mechanism at the molecular level, but evidence has been found for other mechanisms, including inflammation reduction, lipid metabolism, and regulation of cell growth, proliferation and death.

Spermidine is known to regulate plant growth, assisting the in vitro process of transcribing RNA, and inhibition of NOS. Also, spermidine is a precursor to other polyamines, such as spermine and thermospermine, some of which contribute to tolerance against drought and salinity in plants.


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