Spermidine
[CAS# 124-20-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Imide
• Name: Spermidine
• Synonyms: N-(3-Aminopropyl)-1,4-butanediamine; 1,8-Diamino-4-azaoctane
• Molecular Formula: C₇H₁₉N₃
• Molecular Weight: 145.25
• CAS Registry Number: 124-20-9
• EC Number: 204-689-0
• SMILES: C(CCNCCCN)CN

Properties

• Solubility: 1 M (H2O 20 ºC) (Expl.)
• Density: 0.925 g/mL (Expl.)
• Melting point: 22-25 ºC (Expl.)
• Boiling point: 128-130 ºC (14 mmHg) (Expl.)
• Refractive index: 1.479 (Expl.)
• Flash point: 112 ºC

Safety Data

• Hazard Symbols: GHS05 Dander
• Hazard Statements: H314-H318
• Precautionary Statements: P260-P264-P264+P265-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1A	H314

• Transport Information: UN 2735

Discovory and Applicatios

Spermidine, a polyamine compound with the formula C7H19N3, was first discovered in the late 17th century by Dutch scientist Antonie van Leeuwenhoek. He identified crystalline substances in human semen, which were later recognized as polyamines. The isolation and structural elucidation of spermidine came much later in the 20th century, as advancements in analytical techniques allowed for more detailed characterization of polyamines. Spermidine is found in all living cells and plays a critical role in cellular growth, proliferation, and survival.

Spermidine is biosynthesized from putrescine, another polyamine, through the catalytic action of spermidine synthase and decarboxylated S-adenosylmethionine as the aminopropyl donor. The importance of spermidine lies in its role in stabilizing DNA, RNA, and proteins, contributing to the regulation of cell division and gene expression. It is involved in fundamental biological processes such as autophagy, apoptosis, and the modulation of ion channels. Given these functions, spermidine has been extensively studied in the context of cellular physiology and aging.

The discovery of spermidine's ability to promote autophagy—a cellular process responsible for degrading and recycling damaged proteins and organelles—has led to significant interest in its potential health benefits. Autophagy is associated with longevity and improved cellular function. Studies have shown that spermidine supplementation can extend the lifespan of model organisms such as yeast, worms, flies, and mice. This longevity effect is believed to be mediated by its ability to induce autophagy and maintain cellular homeostasis.

In addition to its role in aging, spermidine has shown promise in cardiovascular health. Research indicates that spermidine-rich diets are associated with reduced blood pressure and improved cardiac function. By promoting autophagy in cardiac cells, spermidine helps maintain myocardial integrity and protect against age-related heart disease. Furthermore, spermidine has been investigated for its neuroprotective properties. It may help reduce cognitive decline by preserving neuronal function and mitigating neuroinflammatory processes.

Spermidine also holds potential in cancer research due to its dual role in cell growth and apoptosis. While elevated polyamine levels have been linked to cancer progression, controlled modulation of spermidine levels can promote autophagy-induced cell death in cancer cells, offering a potential therapeutic strategy. Additionally, spermidine is being explored for its role in maintaining gut health by supporting the integrity of intestinal cells and modulating the gut microbiome.

Dietary sources of spermidine include aged cheese, soybeans, mushrooms, whole grains, legumes, and certain vegetables like broccoli and cauliflower. Given its biological importance, spermidine supplements are now marketed for promoting longevity and overall health. However, while promising, clinical research on spermidine's effects in humans is still ongoing, and more studies are needed to fully understand its safety and efficacy.

The discovery of spermidine and its diverse biological functions has significantly contributed to the fields of molecular biology, aging research, and disease prevention. Its ability to promote autophagy and cellular homeostasis positions it as a potential therapeutic agent for age-related diseases, neurodegeneration, and cardiovascular health.

References

1979. Polyamines in Mammalian Biology and Medicine. Perspectives in Biology and Medicine.
DOI: 10.1353/pbm.1979.0013

1991. Role of unsaturated derivatives of spermidine as substrates for spermine synthase and in supporting growth of SV-3T3 cells. The Biochemical Journal.
DOI: 10.1042/bj2740167

2024. DQAsomes as a Coenzyme Q10 Delivery Vehicle: A Step Forward Therapy in Leigh Disease. BioNanoScience.
DOI: 10.1007/s12668-024-01714-4