Grundinformationen
- Standard-SMILES
NCCCCNCCCN- InChIKey
ATHGHQPFGPMSJY-UHFFFAOYSA-N- Summenformel
- C7H19N3
- Durchschnittliche Molmasse
- 145,25 g/mol
- Monoisotopische Masse
- 145,15789761
Überblick
Spermidine is a triamine that is the 1,5,10-triaza derivative of decane. It has a role as an autophagy inducer, a geroprotector and a fundamental metabolite. It is a triamine and a polyazaalkane. It is a conjugate base of a spermidine(3+).
Namen und Bezeichner
- Bevorzugter Name
- Spermidine
- IUPAC
- N'-(3-aminopropyl)butane-1,4-diamine
- Lokaler Name
- 4-Azaoctamethylendiamin
- Englischer Name
- Spermidine
- Summenformel
- C7H19N3
- Molmasse
- 145.25
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
124-20-9- PubChem CID
- 1102
- DTXSID
DTXSID4036645- ChEMBL
CHEMBL19612- ChEBI
CHEBI:16610- UNII
- U87FK77H25
- EC Number
- 204-689-0
- Nikkaji
- J10.054D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1
- Polarare Oberfläche (TPSA)
- 64,1 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 7
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 56,8
Experimentelle und physikochemische Eigenschaften
Melting Point
< 25 °C
< 25 °C
Collision Cross Section
136.5 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
131.9 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
136.2 Ų [M+Na]+
Physikochemische Eigenschaften
- Schmelzpunkt
- 23 · 23-25 °C
- Siedepunkt
- 128 · 128-130 °C (14 mmHg)
- Dichte
- 1 g/mL · 1.00 g/mL at 20 °C
- Brechungsindex
- 20 · n20/D 1.479(lit.)
- Flammpunkt
- 230 °F · >230 °F
- storage temp.
- room temp
- Löslichkeit
- 2 O: · H2O: 1 M at 20 °C, clear, colorless
- Aggregatzustand
- Liquid After Melting
- pka
- 10.53 · 10.53±0.19(Predicted)
- Farbe
- Clear colorless
- Wichte
- 0.925 · 0.925
- PH
- 12 · 12.0-13.5 (25℃, 1M in H2O)
- Geruch (Odor)
- Ichtyal, ammoniacal
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- Miscible with water, ethanol and ether.
- Merck
- 14 · 14,8742
- BRN
- 1698591 · 1698591
- Stabilität
- Stable, but air-sensitive and very hygroscopic - store under argon. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents.
- Kosmetik-Inhaltsstoffe Funktionen
- ANTIOXIDANTHAIR CONDITIONING
- InChI
- 1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2
- InChIKey
- ATHGHQPFGPMSJY-UHFFFAOYSA-N
- SMILES
- NCCCCNCCCN
- CAS Datenbank
- 124 · 124-20-9(CAS DataBase Reference)
- EPA chemische Informationen
- 1 · 1,4-Butanediamine, N-(3-aminopropyl)- (124-20-9)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 83 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Toxikologische Informationen
Toxicity Summary
Uremic toxins such as spermidine are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).
Signs and Symptoms
As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.
Sicherheitsdaten
- F
- 3-10-34
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 2735 8/PG 2
- hs_code
- 29212900
- RTECS-Nr.
- EJ7000000
- risk_code
- 34
- hazard_code
- C
- safety_code
- 26-36/37/39-45-27
- hazard_class
- 8
- packing_group
- III
- Speicherklasse
- 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- Eye Dam. 1Skin Corr. 1B
Chemie und Industrie
Pharmakologische Informationen
Verwendung und Herstellung
Anwendungen
BeschreibungSpermidine is an endogenous polyamine. It is formed from putrescine by spermidine synthase.
Darstellung
synthetischeThe linker resin 2 was used in the synthesis of spermidine. In order to initiate the preparation the 2-nitrossulfonamide was anchored on the resin 2 by reaction in THF under reflux. The resulting resin 3 then reacted with 4-bromobutylphthalimide in acetonitrile in the presence of Cs2CO3 as base, generating the resin 4. Protected spermidine 5 was cleaved from resin 4 after treatment with hydrate hydrazine at room temperature. Spermidine 5 was previously prepared by our group in solution system utilizing Fukuyama's sulfonamide.Synthesis and Characterization of a Linker for Primary Amines used in the Solid Phase Organic Synthesis of SpermidineJ. Braz. Chem. Soc., Vol. 22, No. 1, 86-91, 2011DOI: 10.1590/S0103-50532011000100011
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
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Ergänzende Hinweise
DefinitionChEBI: Spermidine is a triamine that is the 1,5,10-triaza derivative of decane. It is a polyamine that is routinely included in restriction enzyme digestions to improve the cleavage efficacy of the DNA. Spermidine counteracts the inhibitory effects of contaminants coisolated with DNA and consequently permits complete digestion of the DNA at lower enzyme concentrations.
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