ChemicalBook CAS DataBase List 71-44-3

71-44-3

Name	Spermine
CAS	71-44-3
EINECS(EC#)	206-189-8
Molecular Formula	C10H26N4
MDL Number	MFCD00012914
Molecular Weight	202.34
MOL File	71-44-3.mol

Synonyms

1,4-BIS(AMINOPROPYL)BUTANEDIAMINE TETRAHYDROCHLORIDE DIAMINOPROPYLTETRAMETHYLENEDIAMINE HYDROCHLORIDE GERONTINE TETRAHYDROCHLORIDE MUSCULAMINE HYDROCHLORIDE MUSCULAMINE TETRAHYDROCHLORIDE NEURIDINE HYDROCHLORIDE NEURIDINE TETRAHYDROCHLORIDE N,N'-BIS(3-AMINOPROPYL)-1,4-BUTANEDIAMINE 4 H CL N,N'-BIS(3-AMINOPROPYL)-1,4-BUTANEDIAMINE TETRAHYDROCHLORIDE N,N'-BIS-(3-AMINOPROPYL)-1,4-DIAMINOBUTANE TETRAHYDROCHLORIDE N,N'-BIS(3-AMINOPROPYL)-BUTANE-1,4-DIAMINE TETRAHYDROCHLORIDE SPERMINE HYDROCHLORIDE SPERMINE TETRAHYDROCHLORIDE 1,4-Bis(aminopropyl)butanediamine 1,4-Butanediamine, N,N'-bis(3-aminopropyl)- 1,4-Diaminobutane, N,N'-bis(3-aminopropyl)- 4,9-Diaza-1,12-dodecanediamine 4,9-Diazadodecane-1,12-diamine n,n’-bis(3-aminopropyl)-4-butanediamine n,n’-bis(3-aminopropyl)-4-diaminobutane

Chemical Properties

Appearance	White to slightly off-white powder crysta
Melting point	28-30 (lit.)
Boiling point	150 °C/5 mmHg (lit.)
density	0.937
refractive index	1.4850 (estimate)
Fp	>230 °F
storage temp.	2-8°C
solubility	H₂O: 1 M at 20 °C, clear, colorless
form	powder
pka	10.88±0.19(Predicted)
color	Colorless to off-white
biological source	microbial synthetic
Water Solubility	Soluble in chloroform, methanol, water and lower alcohols. Insoluble in ether, benzene and petroleum ether.
Sensitive	Air Sensitive & Hygroscopic
Usage	Biogenic polyamine formed from spermidine and occurring in almost all tissues. Essential for both normal and neoplastic tissue growth. Involved in the modulation of calcium-dependent immune processes
Merck	14,8743
BRN	1751791
Stability:	Hygroscopic
Cosmetics Ingredients Functions	SKIN CONDITIONING
InChI	1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
InChIKey	PFNFFQXMRSDOHW-UHFFFAOYSA-N
SMILES	[H]N(CCCN)CCCCN([H])CCCN
LogP	-0.543 (est)
CAS DataBase Reference	71-44-3(CAS DataBase Reference)
NIST Chemistry Reference	Spermine(71-44-3)
Storage Precautions	Store under nitrogen
EPA Substance Registry System	71-44-3(EPA Substance)

Safety Data

Symbol(GHS)	GHS05
Signal word	Danger
Hazard statements	H318-H314
Precautionary statements	P260h-P301+P330+P331-P303+P361+P353-P405-P501a-P280-P305+P351+P338-P310
Hazard Codes	Xi,C
Risk Statements	R36/38:Irritating to eyes and skin . R34:Causes burns. less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S27:Take off immediately all contaminated clothing . less more
RIDADR	UN 3259 8/PG 2
WGK Germany	3
RTECS	EJ7230000
F	3-10
TSCA	Yes
HazardClass	8
PackingGroup	III
HS Code	29212900
Storage Class	8A - Combustible corrosive hazardous materials
Hazard Classifications	Eye Dam. 1 Skin Corr. 1B

Raw materials And Preparation Products

Hazard Information

Description

Spermine is an endogenous polyamine synthesized from the reaction of spermidine (Item No. 14918) with decarboxylated S-adenosylmethionine in the presence of the enzyme spermine synthase and is required for eukaryotic cell growth and protein synthesis. Intracellular spermine blocks inward rectifying K⁺ channels, whereas extracellular spermine acts as a mixed NMDA glutamate receptor agonist/antagonist at the polyamine site. Spermine has neuroprotective and anti-inflammatory effects and functions as a free radical scavenger to prevent DNA damage by reactive oxygen species.

Chemical Properties

White to slightly off-white powder crysta

Uses

Binds to the polyamine modulatory site of NMDA Spermine is essential for both normal and neoplastic tissue growth. It is involved in the modulation of calcium-dependent immune processes. It plays an important role in cellular proliferation and differentiation as well as inhibits neuronal nitric oxide synthase (nNOS).

Uses

Biogenic polyamine formed from spermidine and occurring in almost all tissues. Essential for both normal and neoplastic tissue growth. Involved in the modulation of calcium-dependent immune processes

Uses

immune modulator

Definition

ChEBI: A polyazaalkane that is tetradecane in which the carbons at positions 1, 5, 10 and 14 are replaced by nitrogens. Spermine has broad actions on cellular metabolism.

General Description

Spermine?is a polyamine, which functions as a free radical scavenger. It modulates gene expression, chromatin stabilization and prevents DNA damage. Spermine inhibits endonuclease-mediated DNA fragmentation.

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).

storage

+4°C (desiccate)

References

[1] fakler b, brndle u, glowatzki e, et al. strong voltage-dependent inward rectification of inward rectifier k+ channels is caused by intracellular spermine[j]. cell, 1995, 80(1): 149-154.
[2] til h p, falke h e, prinsen m k, et al. acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats[j]. food and chemical toxicology, 1997, 35(3): 337-348.

Spectrum Detail

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