334-50-9

Basic information

• Product Name: SPERMIDINE TRIHYDROCHLORIDE
• Synonyms: N-[3-AMINOPROPYL]-1,4-BUTANEDIAMINE 3 H CL;N-(3-AMINOPROPYL)-1 4-BUTANEDIAMINE HYDROCHLORIDE;N-(3-AMINOPROPYL)-1,4-BUTANEDIAMINE TRIHYDROCHLORIDE;N-(3-AMINOPROPYL)-1,4-DIAMINOBUTANE 3HCL;N-(3-AMINOPROPYL)-1,4-DIAMINO-BUTANE TRIHYDROCHLORIDE;SPERMIDINE 3HCL;SPERMIDINE HYDROCHLORIDE;SPERMIDINE TRIHYDROCHLORIDE
• CAS NO: 334-50-9
• Molecular Formula: C₇H₂₂N₃*3Cl
• Molecular Weight: 254.63
• EINECS: 206-379-0
• Product Categories: Glutamate receptor;Glutamate
• Mol File: 334-50-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 257-259 °C(lit.)
• Boiling Point: 246.6 °C at 760 mmHg
• Flash Point: 118.1 °C
• Appearance: White/Crystalline Powder
• Density: 0.906 g/cm³
• Vapor Pressure: 0.0269mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility: Soluble in water
• BRN: 3552356
• CAS DataBase Reference: SPERMIDINE TRIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: SPERMIDINE TRIHYDROCHLORIDE(334-50-9)
• EPA Substance Registry System: SPERMIDINE TRIHYDROCHLORIDE(334-50-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: EJ7023000
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 334-50-9(Hazardous Substances Data)

Usage

Description

Spermidine trihydrochloride, a hydrochloric acid neutralized salt of spermidine, is a polyamine and trivalent organic cation. It is a natural polyamine that plays a crucial role in the regulation of cellular proliferation, differentiation, and cytoprotective macroautophagy/autophagy. External supplementation of spermidine extends lifespan and health span across various species, including yeast, nematodes, flies, and mice. Spermidine trihydrochloride is a more stable form due to the air sensitivity of spermidine. It appears as a white to off-white crystalline powder, soluble in water, very hygroscopic, and air-sensitive.

Uses

Used in Pharmaceutical Applications:
Spermidine trihydrochloride is used as a NOS1 inhibitor and an NMDA and T4 activator for its role in cellular regulation and the stress response in plants. It is also used to purify DNA binding proteins due to its ability to bind and precipitate DNA.
Used in Research and Development:
In the field of research, spermidine trihydrochloride is utilized in Fourier transform infrared spectroscopy (FTIR) characterization and zeta-potential measurements, contributing to the structural and functional study of polyamines.
Used in Chemical and Analytical Applications:
Spermidine trihydrochloride is employed in various chemical and analytical applications due to its chemical properties, such as its solubility in water and hygroscopic nature.

Biological Activity

Binds to the polyamine modulatory site of the NMDA receptor and has been described as an agonist based on its ability to enhance the binding of [ 3 H]-MK801. Spermidine trihydrochloride is an aliphatic polyamine. Its crystalline structure has been studied. It has been reported to preserve the nuclei and prevent proteolytic degradation of histones during the macronuclei isolation from Tetrahymena pyriformis.

Purification Methods

Recrystallise the salt from dry 3% HCl in ethanol and adding dry Et2O if necessary. Filter it off rapidly and dry it in a vacuum desiccator. Alternatively centrifuge the crystals off, wash them with dry Et2O and dry them in a vacuum. [Beilstein 4 IV 1300.]

InChI:InChI=1/C7H19N3.3ClH/c8-4-1-2-6-10-7-3-5-9;;;/h10H,1-9H2;3*1H

Upstream product

• 130750-16-2 {3-[4-(3,5-Dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-butylamino]-propyl}-carbamic acid tert-butyl ester 
• 81065-67-0 N,N',N''-tris(phenylaminothiocarbonyl)-N-(3-aminopropyl)-1,4-diaminobutane 
• 182576-24-5 tert butyl (4 aminobutyl)(3-aminopropyl)carbamate 
• 124-20-9 N-(3-aminopropyl)-1,4-diaminobutane 
• 83392-10-3 N¹,N⁸-bis(tert-butoxycarbonyl)spermidine 
• 191277-07-3 tert-butyl {4-{[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propyl]amino}butyl}carbamate 

Downstream Products

• 189340-47-4 N¹,N⁴,N⁸-tris(mesitylenesulfonyl)spermidine 
• 131086-79-8 3-(4-methoxy-phenyl)-N-{4-[3-(4-methoxy-phenyl)-acryloylamino]-butyl}-N-{3-[3-(4-methoxy-phenyl)-acryloylamino]-propyl}-acrylamide 
• 2465-97-6 N-(4-guanidinylbutyl)-N-(3-guanidinylpropyl)amine 
• 131086-78-7 N¹,N⁵,N¹⁰-tri-<(E)-p-coumaroyl>-spermidine 
• 189340-59-8 N¹,N⁸-diethyl-N¹,N⁴,N⁸-tris(mesitylenesulfonyl)spermidine 
• 189340-64-5 N¹,N⁸-dipropyl-N¹,N⁴,N⁸-tris(mesitylenesulfonyl)spermidine 
• 97141-40-7 1,8-di(ethylamino)-4-azaoctane 
• 124-20-9 N-(3-aminopropyl)-1,4-diaminobutane 

Relevant articles and documents

Spermidinium closo-dodecaborate-encapsulating liposomes as efficient boron delivery vehicles for neutron capture therapy

closo-Dodecaborate-encapsulating liposomes were developed as boron delivery vehicles for neutron capture therapy. The use of spermidinium as a counter cation of closo-dodecaborates was essential not only for the preparation of high boron content liposome solutions but also for efficient boron delivery to tumors. This journal is

Method for synthesizing spermidine hydrochloride

The invention relates to a method for synthesizing spermidine hydrochloride. The reaction formula is shown as the following formula (I) which is described in the specification. In the formula (I), theprotective group R1 of amino in 4-amino-1-butanol of a compound 2 is one of tert-butyloxycarboryl Boc-, triphenylmethyl Trt- and p-methoxytriphenylmethyl Mmt-, and a protective group R2 of propane diamine of the compound is one of tert-butyloxycarbonyl Boc-, triphenylmethyl Trt- and p-methoxytriphenylmethyl (Mmt-). A reagent used in the Mitsunobo reaction condition is one of triphenylphosphine, di-tert-butyl azodicarboxylate, diethyl azodicarboxylate and diisopropyl azodicarboxylate. The preparation method disclosed by the invention is simple in required process condition, mild in reaction condition, capable of effectively obtaining spermidine hydrochloride, relatively short in synthesis step and relatively high in synthesis yield.

Aliphatic Amino Azides as Key Building Blocks for Efficient Polyamine Syntheses

New routes to open-chain polyamines have been developed using aliphatic amino azides as common precursors for the construction of the carbon-nitrogen framework.These α,ω-diaminoalkane synthetic equivalents were combined with (ω-halogenalkyl)dichloroboranes to extend the polyamine chain from the azido moiety.An extension from the free amino group can also be achieved via a Michael type addition with acrylonitrile or a reductive amination with a γ-azido ketone.Further transformations led to a large variety of regioselectively C- or (and) N-substituted polyamines.