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| Names | |
|---|---|
| Preferred IUPAC name N1,N4-Bis(3-aminopropyl)butane-1,4-diamine | |
| Identifiers | |
3D model (JSmol) | |
| 1750791 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| DrugBank |
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| ECHA InfoCard | 100.000.686 |
| EC Number |
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| 454653 | |
| KEGG |
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| MeSH | Spermine |
| RTECS number |
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| UNII |
|
| UN number | 3259 |
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| Properties | |
| C10H26N4 | |
| Molar mass | 202.346 g·mol−1 |
| Appearance | Colourless crystals |
| Odor | Fishy or like that of semen |
| Density | 917 mg mL−1 |
| Melting point | 28 to 30 °C (82 to 86 °F; 301 to 303 K) |
| Boiling point | 150.1 °C; 302.1 °F; 423.2 K at 700 Pa |
| logP | −0.543 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | corrosive |
| GHS labelling: | |
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| Danger | |
| H314 | |
| P280,P305+P351+P338,P310 | |
| Flash point | 110 °C (230 °F; 383 K) |
| Related compounds | |
Related compounds | Spermidine,Putrescine,Cadaverine,Diethylenetriamine,Norspermidine,Thermospermine |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Spermine is apolyamine involved incellular metabolism that is found in alleukaryotic cells. The precursor for synthesis of spermine is the amino acidornithine. It is an essentialgrowth factor in somebacteria as well. It is found as apolycation at physiological pH. Spermine is associated withnucleic acids and is thought to stabilize helical structure, particularly inviruses. It functions as an intracellularfree radical scavenger to protect DNA from free radical attack.[1] Spermine is the chemical primarily responsible for the characteristic odor of semen.[2]
Antonie van Leeuwenhoek first described crystals of sperminephosphate in humansemen in 1678.[3] The namespermin was first used by the German chemistsLadenburg and Abel in 1888,[4][5] and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling)[6][7] and Germany (by Wrede et al.).[8]
Aderivative of spermine, N1, N12-bis(ethyl)spermine (also known as BESm) was investigated in the late 1980s along with similarpolyamine analogues for its potential as acancer therapy.[9][10]
Spermine biosynthesis in animals starts withdecarboxylation ofornithine by the enzymeOrnithine decarboxylase in the presence ofPLP. This decarboxylation givesputrescine. Thereafter theenzymespermidine synthase effects twoN-alkylation bydecarboxy-S-adenosyl methionine. The intermediate isspermidine.
Plants employ additional routes to spermine. In one pathway L-glutamine is the precursor to L-ornithine, after which the synthesis of spermine from L-ornithine follows the same pathway as in animals.
Another pathway in plants starts with decarboxylation of L-arginine to produceagmatine. The imine functional group in agmatine then is hydrolysed byagmatine deiminase, releasingammonia, converting theguanidine group into a urea. The resultingN-carbamoylputrescine is acted on by ahydrolase to split off the urea group, leavingputrescine. After that the putrescine follows the same pathway to completing the synthesis of spermine.[11]
| Authority control databases: National |
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