4-(3-アミノプロピルアミノ)-1-ブタンアミン

Spermidine

HCID 1102

基本情報

CAS
124-20-9
標準SMILES
NCCCCNCCCN
InChIKey
ATHGHQPFGPMSJY-UHFFFAOYSA-N
分子式
C7H19N3
平均分子量
145.25 g/mol
単同位体質量
145.15789761

概要

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+).

名称と識別子

優先名称
Spermidine
IUPAC
N'-(3-aminopropyl)butane-1,4-diamine
現地名
4-(3-アミノプロピルアミノ)-1-ブタンアミン
英語名
Spermidine
分子式
C7H19N3
分子量
145.25

名称と別名

spermidine124-20-91,5,10-Triazadecane4-Azaoctamethylenediamine4-Azaoctane-1,8-diamineSpermidinN-(3-aminopropyl)butane-1,4-diamine1,8-Diamino-4-azaoctaneN-(3-Aminopropyl)-1,4-butanediamineN'-(3-aminopropyl)butane-1,4-diamine1,4-Butanediamine, N-(3-aminopropyl)-1,4-Butanediamine, N1-(3-aminopropyl)-
名称をさらに表示
スペルミジン(3-アミノプロピル)(4-アミノブチル)アミン4-(3-アミノプロピルアミノ)-1-ブタンアミン4-アザ-1,8-オクタンジアミンN-(3-アミノプロピル)-1,4-ブタンジアミン3-アミノプロピル4-アミノブチルアミン4-[(3-アミノプロピル)アミノ]ブタン-1-アミン4-アザオクタン-1,8-ジアミンN-(3-アミノプロピル)テトラメチレンジアミンスペルミジン標準品0.1 Mスペルミジン 溶液スペルミジン, 99%N1-(3-AMINOPROPYL)BUTANE-1,4-DIAMINESpermidine-Rich Wheat Germ ExtractSpermidine,99%SPERMIDINE FREE BASE3.2 KgSpermidieSpemidine
(4-aminobutyl)(3-aminopropyl)amineN-(3-Aminopropyl)-1,4-butane-diamine1,4-Diaminobutane, N-(3-aminopropyl)-N-(4-Aminobutyl)-1,3-diaminopropaneU87FK77H25CHEBI:16610RefChem:184613204-689-0

データベース識別子

CAS
124-20-9
PubChem CID
1102
DTXSID
DTXSID4036645
ChEMBL
CHEMBL19612
ChEBI
CHEBI:16610
UNII
U87FK77H25
EC Number
204-689-0
Nikkaji
J10.054D

物性

構造計算による物性

XLogP
-1
極性表面積
64.1 Ų
水素結合供与体数
3
水素結合受容体数
3
回転可能結合数
7
重原子数
10

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
FragrancesFragrance Ingredient (1,4-Butanediamine, N-(3-aminopropyl)-) -> IFRA transparency List
Melting Point · 2 件

< 25 °C

< 25 °C

Physical DescriptionSolid
Collision Cross Section · 3 件

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]+

物理化学的性質

融点
23 · 23-25 °C
沸点
128 · 128-130 °C (14 mmHg)
比重(密度)
1 g/mL · 1.00 g/mL at 20 °C
屈折率
20 · n20/D 1.479(lit.)
闪点
230 °F · >230 °F
貯蔵温度
room temp

化学的性質

化学的特性Spermidine solution is a colorless clear liquid with very hygroscopic and oxidizable. It is soluble in water (50 mg/ml), ethanol, and ether.

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Regulatory InformationSpermidine: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Corr. 1A (100%)

毒性情報

TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary · 1 件

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 · 1 件

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.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

F
3-10-34
wgk
3
tsca
TSCA listed
rtecs
EJ7000000
ridadr
UN 2735 8/PG 2
hs_code
29212900

化学と産業

薬理情報

Metabolism/MetabolitesUremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite PathwaysCystathionine Beta-Synthase Deficiency

用途と製造

UsesNaturally produced by the body (endogenous).
Use ClassificationFragrance Ingredients
General Manufacturing Information1,4-Butanediamine, N1-(3-aminopropyl)-: ACTIVE

応用分野

解説すべての生体中に存在するポリアミンの一種.N-(3-アミノプロピル)-1,4-ブタンジアミン.DNA二重らせん構造の安定化と変化,RNAの安定化,RNAやDNAポリメラーゼの活性化などの生理作用を示す.

説明Spermidine is an endogenous polyamine. It is formed from putrescine by spermidine synthase.

調製方法 · 1 件

製造方法The 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

サプライヤー100 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
補足説明 · 1 件

定義ChEBI: 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.

関連反応

24 件

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