Spermidine

HCID 1102
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Basic information

CAS
124-20-9
Standard SMILES
NCCCCNCCCN
InChIKey
ATHGHQPFGPMSJY-UHFFFAOYSA-N
Molecular formula
C7H19N3
Average molar mass
145.25 g/mol
Monoisotopic mass
145.15789761

Overview

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+).

Names & identifiers

Preferred name
Spermidine
IUPAC
N'-(3-aminopropyl)butane-1,4-diamine
English name
Spermidine
Molecular formula
C7H19N3
Molecular weight
145.25

Names & synonyms

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)-
Show more names
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

Database identifiers

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

Properties

Computed structural properties

XLogP
-1
Topological polar surface area
64.1 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
3
Rotatable bonds
7
Heavy atoms
10

Experimental & physicochemical properties

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

< 25 °C

< 25 °C

Physical DescriptionSolid
Collision Cross Section · 3 items

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]+

Physicochemical properties

Melting point
23 · 23-25 °C
Boiling point
128 · 128-130 °C (14 mmHg)
Density
1 g/mL · 1.00 g/mL at 20 °C
refractive index
20 · n20/D 1.479(lit.)
Flash point
230 °F · >230 °F
storage temp.
room temp

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

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

Toxicology

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 item

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 item

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).

Safety data

F
3-10-34
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
EJ7000000
ridadr
UN 2735 8/PG 2

Chemistry & industry

Pharmacology

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

Uses & manufacturing

UsesNaturally produced by the body (endogenous).
Use ClassificationFragrance Ingredients
General Manufacturing Information1,4-Butanediamine, N1-(3-aminopropyl)-: ACTIVE
Applications · 2 items

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

UsesSpermidine can be used in electroporation while transferring the DNA into the cell under the electrical impulse. May be used for purification of DNA-binding proteins. Spermidine is also used, along with calcium chloride, for precipitating DNA onto microprojectiles for bombardment with a gene gun.

Preparation methods · 1 item

PreparationThe 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

Upstream & downstream products

Suppliers100 total

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]
Additional notes · 1 item

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.

Related reactions

24 records
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Compound notes

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