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agmatine

Structure via PubChem · Public domain (PubChem)

EntityQ394317· pop 19· linked from 206 articles

Also 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

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 sections
Contents
  • 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.

Gallery (3)