Structure via PubChem · Public domain (PubChem)
agmatine
Sign in to saveAlso known as N-(4-aminobutyl)guanidine, 2-(4-aminobutyl)guanidine, 1-Amino-4-guanidinobutane, 4-Guanidino-1-butanamine, Argmatine, N-(Aminoiminomethyl)-1,4-Butanediamine, N-4-Aminobutylguanidine, (4-Aminobutyl)guanidine
Agmatine, also known as 4-aminobutyl-guanidine, was discovered in 1910 by Albrecht Kossel. It is a chemical substance which is naturally created from the amino acid arginine. Agmatine has been shown to exert modulatory action at multiple molecular targets, notably: neurotransmitter systems, ion channels, nitric oxide (NO) synthesis, and polyamine metabolism and this provides bases for further research into potential pharmacological applications.
Chemical data
- Formula
- C5H14N4
- Molecular weight
- 130.19 g/mol
- IUPAC name
- 2-(4-aminobutyl)guanidine
- SMILES
- C(CCN=C(N)N)CN
- InChIKey
- QYPPJABKJHAVHS-UHFFFAOYSA-N
- XLogP
- -1.5
- Polar surface area
- 90.4 Ų
- H-bond donors
- 3
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,917 papers- Neuroprotection by agmatine: Possible involvement of the gut microbiome?Ageing research reviews · 2023
- Neuroprotective offerings by agmatine.Neurotoxicology · 2019
- Perspectives on Agmatine Neurotransmission in Acute and Chronic Stressrelated Conditions.Mini reviews in medicinal chemistry · 2023
- Agmatine as a novel intervention for Alzheimer's disease: Pathological insights and cognitive benefits.Ageing research reviews · 2024
- Pharmacological profile of agmatine: An in-depth overview.Neuropeptides · 2024
via PubMed
Wikidata facts
- Mass
- 130.122
Show 5 more facts
- chemical formula
- C₅H₁₄N₄
- found in taxon
- Wisteria floribunda
- canonical SMILES
- C(CCN=C(N)N)CN
- Commons category
- Agmatine
- subject has role
- primary metabolite
Sources (5)
via Wikidata · CC0
~7 min read
Encyclopedic overview
14 sectionsContents
- History
- Metabolic pathways
- Mechanisms of action
- Food consumption
- Pharmacokinetics
- Research
- Cardiovascular
- Glucose regulation
- Kidney functions
- Neurotransmission
- Opioid liability
- See also
- References
- Further reading
Agmatine, also known as 4-aminobutyl-guanidine, was discovered in 1910 by Albrecht Kossel. It is a chemical substance which is naturally created from the amino acid arginine. Agmatine has been shown to exert modulatory action at multiple molecular targets, notably: neurotransmitter systems, ion channels, nitric oxide (NO) synthesis, and polyamine metabolism and this provides bases for further research into potential pharmacological applications.
==History== The term agmatine stems from A- (for amino-) + g- (from guanidine) + -ma- (from ptomaine) + -in (German)/-ine (English) suffix with insertion of -t- apparently for euphony. A year after its discovery, it was found that agmatine could increase blood flow in rabbits; however, the physiological relevance of these findings were questioned given the high concentrations (high μM range) required. In the 1920s, researchers in the diabetes clinic of Oskar Minkowski showed that agmatine can exert mild hypoglycemic effects. In 1994, endogenous agmatine synthesis in mammals was discovered.
Excerpted from Wikipedia’s “agmatine” article, available under the CC BY-SA 4.0 licence.