Spermidine

Base Information

• Chemical Name: Spermidine
• CAS No.: 124-20-9
• Molecular Formula: C7H19N3
• Molecular Weight: 145.248
• Hs Code.: 29212900
• European Community (EC) Number: 204-689-0
• UNII: U87FK77H25
• DSSTox Substance ID: DTXSID4036645
• Nikkaji Number: J10.054D
• Wikipedia: Spermidine
• Wikidata: Q418834
• NCI Thesaurus Code: C129012
• Pharos Ligand ID: FLBC2PSAPDXM
• Metabolomics Workbench ID: 37687
• ChEMBL ID: CHEMBL19612
• Mol file: 124-20-9.mol

Synonyms:1,4-Butanediamine,N-(3-aminopropyl)- (8CI,9CI);Spermidine (6CI);1,5,10-Triazadecane;1,8-Diamino-4-azaoctane;4-Azaoctane-1,8-diamine;N-(3-Aminopropyl)-1,4-butanediamine;N-(3-Aminopropyl)-1,4-diaminobutane;N-(3-Aminopropyl)-4-aminobutylamine;N-(4-Aminobutyl)-1,3-diaminopropane;Spermidine;

Chemical Property of Spermidine

Chemical Property:

• Appearance/Colour: Colorless clear liquid
• Vapor Pressure: 0.0269mmHg at 25°C
• Melting Point: 23-25 °C
• Refractive Index: n20/D 1.479(lit.)
• Boiling Point: 246.57 °C at 760 mmHg
• PKA: 10.53±0.19(Predicted)
• Flash Point: 118.078 °C
• PSA: 64.07000
• Density: 0.906 g/cm³
• LogP: 1.45520
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility.: Miscible with water, ethanol and ether.
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 145.157897619
• Heavy Atom Count: 10
• Complexity: 56.8

Purity/Quality:

99% ^*data from raw suppliers

Spermidine Free Base ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CCNCCCN)CN
• Recent ClinicalTrials: Spermidine Anti-Hypertension Study
• Recent EU Clinical Trials: Characterisation of the effects of Spermidine on the immune response to Covid-19 vaccine in older people - a feasibility study
• General Description: Spermidine is a naturally occurring polyamine involved in cellular growth regulation and protein synthesis, with potential implications in cancer therapy due to its role in modulating ornithine decarboxylase (ODC) activity and influencing neoplastic cell proliferation. Its analogs and derivatives have been explored for their antineoplastic properties, particularly in targeting malignancies such as melanoma and carcinoma. Additionally, spermidine's interaction with ODC highlights its significance in polyamine metabolism, making it a candidate for therapeutic interventions aimed at inhibiting aberrant cellular growth.

Technology Process of Spermidine

There total 40 articles about Spermidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

4-aza-1,3-bis(1,3-dibenzylhexahydro-2-oxo-1,3,5-triazin-5-yl)octane (143565-69-9) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Guidance literature:

With piperidine; In methanol; at 65 ℃;

DOI:10.1021/jo00049a036

Reference yield: 79.5%

[4-(3-aminopropylamino)butyl]carbamic acid tert-butyl ester (103493-34-1) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Guidance literature:

With hydrogenchloride; In methanol; for 4h; Cooling with ice;

Reference yield: 78.5%

spermidine trihydrochloride (334-50-9,35408-56-1) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9)

Guidance literature:

With sodium methylate; In methanol; for 3h; Reagent/catalyst; Solvent; Reflux; Large scale;

upstream raw materials:

N⁸-acetylspermidine dihydrochloride

N-(cyanoethyl)-1,4-diaminobutane

Spermine

kinetin

Downstream raw materials:

N-3-Phenylpropyl-N'-<3-(3-phenylpropylamino)-propyl>-butan-1,4-diamin-trihydrochlorid

N¹,N¹⁰-bisphthaloylspermidine

N¹,N⁸-dicinnamoyl spermidine

N¹,N⁸-bis(benzoyl)spermidine

Refernces

Synthesis of new polyamine derivatives for cancer chemotherapeutic studies

10.1002/jps.2600700835

The research focuses on the synthesis and biological evaluation of new polyamine derivatives for potential cancer chemotherapeutic applications. The purpose of the study was to investigate the effects of various homologs, analogs, and acylated derivatives of spermine and spermidine, as well as several heterocyclic and aromatic compounds containing a novoldiamine side chain, on the growth of neoplastic cells. The researchers hypothesized that these compounds could be useful in oncology due to the role of polyamines in cellular protein synthesis and the structure and activity of tRNA. The study concluded that several of these compounds showed activity against B-16 melanoma and human epidermoid carcinoma of the nasopharynx. Key chemicals used in the synthesis process included N,N-Bis(2-cyanoethyl)amine, 1-methylpiperazin, 1,4'-bipiperidine, novoldiamine, and various acylating agents such as palmitoyl chloride. The biological testing involved the use of alloxanized mice for hypoglycemic activity and various cell cultures for antineoplastic activity.

Catalytic Irreversible Inhibition of Mammalian Ornithine Decarboxylase (E.C. 4.1.1.17) by Substrate and Product Analogues

10.1021/ja00476a050

The study investigates the catalytic irreversible inhibition of mammalian ornithine decarboxylase (ODC) by substrate and product analogues. The chemicals involved include the diamine putrescine and the polyamines spermidine and spermine, which are implicated in growth regulation. The researchers synthesized and tested various inhibitors, such as 5-hexyne-1,4-diamine (2) and trans-hex-2-en-5-yne-1,4-diamine (3), to determine their effects on ODC. They found that these compounds irreversibly inactivated ODC by forming covalent bonds with the enzyme's active site. The study also explores the mechanisms of inhibition, proposing that the inhibitors are activated by the enzyme itself, leading to the formation of reactive intermediates that bind to the enzyme. This research provides valuable insights into the design of specific, irreversible inhibitors for ODC and other decarboxylases, which could have significant implications for understanding the biological roles of polyamines and for potential therapeutic applications.

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