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agmatine
4-guanidino-1-butanamine

Supplier Sponsors

Name:2-(4-aminobutyl)guanidine
CAS Number: 306-60-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:206-187-7
FDA UNII: 70J407ZL5Q
Nikkaji Web:J11.608D
MDL:MFCD00013109
XlogP3-AA:-1.50 (est)
Molecular Weight:130.19458000
Formula:C5 H14 N4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 234.80 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.100000 mmHg @ 25.00 °C. (est)
Flash Point: 204.00 °F. TCC ( 95.80 °C. ) (est)
logP (o/w): -1.550 (est)
Soluble in:
 water, 9.002e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
AGMATINE SULFATE ENDOGENOUS AGONIST AT 95%
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for agmatine usage levels up to:
 not for fragrance use.
 
Recommendation for agmatine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :199
National Institute of Allergy and Infectious Diseases:Data
2-(4-aminobutyl)guanidine
Chemidplus:0000306605
 
References:
 2-(4-aminobutyl)guanidine
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):199
Pubchem (sid):134974292
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C00179
HMDB (The Human Metabolome Database):HMDB01432
FooDB:FDB008310
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 barley
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 bean winged bean
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 pea white pea
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 sesame leaf
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 sesame seed
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 soybean seed
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Synonyms:
1-amino-4-guanidinobutane
1-amino-4-guanidobutane
(4-aminobutyl) guanidine
(4-aminobutyl)-guanidine
1-(4-aminobutyl)guanidin
(4-aminobutyl)guanidine
1-(4-aminobutyl)guanidine
2-(4-aminobutyl)guanidine
4-(aminobutyl)guanidine
N-(4-aminobutyl)guanidine
N-4-aminobutylguanidine
N-(aminoiminomethyl)-1,4-butanediamine
 argmatine
 guanidine, (4-aminobutyl)-
 guanidine, (4-aminobutyl)- (8CI)(9CI)
 guanidine, N-(4-aminobutyl)-
 guanidine, N''-(4-aminobutyl)-
4-guanidino-1-butanamine
4-guanidinobutylamine
 

Articles:

PubMed:A UHPLC method for the simultaneous analysis of biogenic amines, amino acids and ammonium ions in beer.
PubMed:Validation of the Biofish-300 HIS Enzymatic Biosensor for the Detection of Histamine in Fishery Products.
PubMed:Technological Factors Affecting Biogenic Amine Content in Foods: A Review.
PubMed:Putrescine biosynthesis in Lactococcus lactis is transcriptionally activated at acidic pH and counteracts acidification of the cytosol.
PubMed:Determination of biogenic amines in licorice (Glycyrrhiza glabra) by ion-pair extraction and liquid chromatography-tandem mass spectrometry.
PubMed:Functional Study of Lysine Decarboxylases from Klebsiella pneumoniae in Escherichia coli and Application of Whole Cell Bioconversion for Cadaverine Production.
PubMed:Quality assurance of histamine analysis in fresh and canned fish.
PubMed:Putrescine production by Lactococcus lactis subsp. cremoris CECT 8666 is reduced by NaCl via a decrease in bacterial growth and the repression of the genes involved in putrescine production.
PubMed:Mechanistic studies of the agmatine deiminase from Listeria monocytogenes.
PubMed:Determination of benzoxazinoids in wheat and rye beers by HPLC-DAD and UPLC-QTOF MS.
PubMed:Implementation of the agmatine-controlled expression system for inducible gene expression in Lactococcus lactis.
PubMed:A Fusarium graminearum strain-comparative proteomic approach identifies regulatory changes triggered by agmatine.
PubMed:The Impact of Carvacrol on Ammonia and Biogenic Amine Production by Common Foodborne Pathogens.
PubMed:Analysis of 17 neurotransmitters, metabolites and precursors in zebrafish through the life cycle using ultrahigh performance liquid chromatography-tandem mass spectrometry.
PubMed:AguR, a Transmembrane Transcription Activator of the Putrescine Biosynthesis Operon in Lactococcus lactis, Acts in Response to the Agmatine Concentration.
PubMed:Polyamines in conventional and organic vegetables exposed to exogenous ethylene.
PubMed:Fast determination of biogenic amines in beverages by a core-shell particle column.
PubMed:Lactose-mediated carbon catabolite repression of putrescine production in dairy Lactococcus lactis is strain dependent.
PubMed:Agmatine attenuates hyperactivity and weight loss associated with activity-based anorexia in female rats.
PubMed:Bioactive amines in Mozzarella cheese from milk with varying somatic cell counts.
PubMed:Discriminative stimulus effects of the imidazoline I2 receptor ligands BU224 and phenyzoline in rats.
PubMed:An agmatine-inducible system for the expression of recombinant proteins in Enterococcus faecalis.
PubMed:Bioactive amines in sorghum: method optimisation and influence of line, tannin and hydric stress.
PubMed:Putrescine production via the agmatine deiminase pathway increases the growth of Lactococcus lactis and causes the alkalinization of the culture medium.
PubMed:Discriminative stimulus effects of the novel imidazoline I₂ receptor ligand CR4056 in rats.
PubMed:Long-term (5 years), high daily dosage of dietary agmatine--evidence of safety: a case report.
PubMed:The gluconeogenesis pathway is involved in maintenance of enterohaemorrhagic Escherichia coli O157:H7 in bovine intestinal content.
PubMed:Characterization of imidazoline receptors in blood vessels for the development of antihypertensive agents.
PubMed:[Protective effects of agmatine on lipopolysaccharide -induced acute hepatic injury in mice].
PubMed:Quality changes of anchovy (Stolephorus heterolobus) under refrigerated storage of different practical industrial methods in Thailand.
PubMed:Evidence for oral agmatine sulfate safety--a 95-day high dosage pilot study with rats.
PubMed:Quality properties, fatty acids, and biogenic amines profile of fresh tilapia stored in ice.
PubMed:Involvement of imidazoline system in drug addiction.
PubMed:The putrescine biosynthesis pathway in Lactococcus lactis is transcriptionally regulated by carbon catabolic repression, mediated by CcpA.
PubMed:Novel touchdown-PCR method for the detection of putrescine producing gram-negative bacteria in food products.
PubMed:Melatonin is formed during winemaking at safe levels of biogenic amines.
PubMed:Regulation of metabolic products and gene expression in Fusarium asiaticum by agmatine addition.
PubMed:A multiresidual method based on ion-exchange chromatography with conductivity detection for the determination of biogenic amines in food and beverages.
PubMed:Biogenic amines in low- and reduced-fat dry fermented sausages formulated with konjac gel.
PubMed:Stimulation of cadaverine production by foodborne pathogens in the presence of Lactobacillus, Lactococcus, and Streptococcus spp.
PubMed:Focused review: agmatine in fermented foods.
PubMed:Expression of the arginine deiminase pathway genes in Lactobacillus sakei is strain dependent and is affected by the environmental pH.
PubMed:Is the production of the biogenic amines tyramine and putrescine a species-level trait in enterococci?
PubMed:Biogenic amines and potential histamine - Forming bacteria in Rihaakuru (a cooked fish paste).
PubMed:Independent evolutionary origins of functional polyamine biosynthetic enzyme fusions catalysing de novo diamine to triamine formation.
PubMed:Expression of Lactobacillus brevis IOEB 9809 tyrosine decarboxylase and agmatine deiminase genes in wine correlates with substrate availability.
PubMed:Agmatine in the hypothalamic paraventricular nucleus stimulates feeding in rats: involvement of neuropeptide Y.
PubMed:Control of biogenic amines in food--existing and emerging approaches.
PubMed:Dimethylamine, trimethylamine, and biogenic amine formation in high-pressure processed semidried squid (Todarodes pacificius) during refrigerated storage.
PubMed:Simultaneous quantification of eight biogenic amine compounds in tuna by matrix solid-phase dispersion followed by HPLC-orbitrap mass spectrometry.
PubMed:The role of two families of bacterial enzymes in putrescine synthesis from agmatine via agmatine deiminase.
PubMed:Amino acids improve acid tolerance and internal pH maintenance in Bacillus cereus ATCC14579 strain.
PubMed:Post-mortem changes in farmed spotted Babylon snail (Babylonia areolata) during iced storage.
PubMed:Production of biogenic amines by lactic acid bacteria and enterobacteria isolated from fresh pork sausages packaged in different atmospheres and kept under refrigeration.
PubMed:Occurrence of biogenic amine-forming lactic acid bacteria in wine and cider.
PubMed:Polyamine biosynthetic diversity in plants and algae.
PubMed:Determination of biogenic amines in Korean traditional fermented soybean paste (Doenjang).
PubMed:Bioactive amines and quality of egg from Dekalb hens under different storage conditions.
PubMed:A new ultra-pressure liquid chromatography method for the determination of biogenic amines in cheese.
PubMed:A method for benzoyl chloride derivatization of biogenic amines for high performance liquid chromatography.
PubMed:lmo0038 is involved in acid and heat stress responses and specific for Listeria monocytogenes lineages I and II, and Listeria ivanovii.
PubMed:Comparative survey of putrescine production from agmatine deamination in different bacteria.
PubMed:Nucleotide degradation and biogenic amine formation of wild white grouper (Epinephelus aeneus) stored in ice and at chill temperature (4°C).
PubMed:Supraspinally-administered agmatine attenuates the development of oral fentanyl self-administration.
PubMed:Factors affecting the production of putrescine from agmatine by Lactobacillus hilgardii XB isolated from wine.
PubMed:Determination of biogenic amines in squid and white prawn by high-performance liquid chromatography with postcolumn derivatization.
PubMed:Determination of biogenic amines in alcoholic beverages by ion chromatography with suppressed conductivity detection and integrated pulsed amperometric detection.
PubMed:Biogenic amine formation and nitrite reactions in meat batter as affected by high-pressure processing and chilled storage.
PubMed:Arginine-dependent acid resistance in Salmonella enterica serovar Typhimurium.
PubMed:Relation of biogenic amines' formation with microbiological and sensory attributes in Lactobacillus-inoculated vacuum-packed rainbow trout (Oncorhynchus mykiss) fillets.
PubMed:Determination of biogenic amines by capillary zone electrophoresis with conductometric detection.
PubMed:Influence of cultivar and germination on bioactive amines in soybeans (Glycine max L. Merril).
PubMed:Volatile and biogenic amines, microbiological counts, and bacterial amino acid decarboxylase activity throughout the salt-ripening process of anchovies (Engraulis encrasicholus).
PubMed:Development of agmatine sensor using the combination of putrescine oxidase and agmatinase for squid freshness.
PubMed:New solvent systems for thin-layer chromatographic determination of nine biogenic amines in fish and squid.
PubMed:Differences between biogenic amine detection by HPLC methods using OPA and dansyl derivates.
PubMed:Relation of biogenic amines with microbial and sensory changes of whole and filleted freshwater rainbow trout (Onchorynchus mykiss) stored on ice.
PubMed:Biogenic amines in restructured beef steaks as affected by added walnuts and cold storage.
PubMed:On-line solid-phase extraction with surfactant accelerated on-column derivatization and micellar liquid chromatographic separation as a tool for the determination of biogenic amines in various food substrates.
PubMed:Determination of biogenic amines as their benzoyl derivatives after cloud point extraction with micellar liquid chromatographic separation.
PubMed:The diverse bacterial origins of the Arabidopsis polyamine biosynthetic pathway.
PubMed:Identification of the putrescine biosynthetic genes in Pseudomonas aeruginosa and characterization of agmatine deiminase and N-carbamoylputrescine amidohydrolase of the arginine decarboxylase pathway.
PubMed:Comparison of a capillary electrophoresis method with high-performance liquid chromatography for the determination of biogenic amines in various food samples.
PubMed:[Imidazoline receptors-normal and pathological factors].
PubMed:Effects of NG-nitro-L-arginine methyl ester, 7-nitro indazole, and agmatine on pentylenetetrazol-induced discriminative stimulus in Long-Evans rats.
PubMed:Sensory, chemical and bacteriological changes during storage of iced squid (Todaropsis eblanae).
PubMed:Sensory, chemical and bacteriological changes in vacuum-packed pressurised squid mantle (Todaropsis eblanae) stored at 4 degrees C.
PubMed:Biogenic amine accumulation in ripened sausages affected by the addition of sodium sulphite.
PubMed:Molecular characterization and regulation of the aguBA operon, responsible for agmatine utilization in Pseudomonas aeruginosa PAO1.
PubMed:[The content of biogenic amines in canned fish from the Turkish market].
PubMed:Formation of biogenic amines in bulk-stored chilled hake (Merluccius merluccius L.) packed under atmospheres.
PubMed:The CbrA-CbrB two-component regulatory system controls the utilization of multiple carbon and nitrogen sources in Pseudomonas aeruginosa.
PubMed:Growth and metabolic activity of Shewanella putrefaciens maintained under different CO2 and O2 concentrations.
PubMed:Biogenic amine production by Lactobacillus.
PubMed:Changes in biogenic amine and polyamine contents in slightly fermented sausages manufactured with and without sugar.
PubMed:Liquid chromatographic determination of biogenic amines in fermented foods after derivatization with 3,5-dinitrobenzoyl chloride.
PubMed:Redox hydrogel-based amperometric bienzyme electrodes for fish freshness monitoring
PubMed:Effect of proteolytic starter cultures of Staphylococcus spp. on biogenic amine formation during the ripening of dry fermented sausages.
PubMed:Changes in polyamines and ethylene during the development and ripening of eggplant fruits (Solanum melongena).
PubMed:Biogenic amines and sensory changes associated with the microbial flora of Mediterranean gilt-head sea bream (Sparus aurata) stored aerobically at 0, 8, and 15 degrees C.
PubMed:Determination of biogenic amines in cheese.
PubMed:Polyamine content of ordinary foodstuffs and various fermented foods.
PubMed:Overexpression of arginine decarboxylase in transgenic plants.
PubMed:Liquid chromatographic method for determination of biogenic amines in fish and fish products.
PubMed:Biogenic amines and microbial quality of sprouts.
PubMed:Determination of biogenic amines in leafy vegetables by amino acid analyser.
PubMed:Studies on the biosynthesis of tropane alkaloids in Datura stramonium L. transformed root cultures : 2. On the relative contributions of L-arginine and L-ornithine to the formation of the tropane ring.
PubMed:Studies on the biosynthesis of tropane alkaloids in Datura stramonium L. transformed root cultures : 1. The kinetics of alkaloid production and the influence of feeding intermediate metabolites.
PubMed:Enzymes of N-methylputrescine biosynthesis in relation to hyoscyamine formation in transformed root cultures of Datura stramonium and Atropa belladonna.
PubMed:Determination of mono-, di- and polyamines in foods using a single-column amino acid auto-analyzer.
PubMed:Mutagenicity of pyrolysates from guanidine, ureide, secondary amines and polyamines found by the Salmonella/mammalian-microsome test.
PubMed:Alkylating activity of processed fish products treated with sodium nitrite in simulated gastric juice.
PubMed:Occurrence of methylguanidine and agmatine, nitrosatable guanidino compounds, in foods.
PubMed:Occurrence of methylguanidine and agmatine in foods.
 
Notes:
decarboxylated arginine, isolated from several plant and animal sources, e.g., pollen, ergot, herring sperm, octopus muscle. Agmatine ((4-aminobutyl)guanidine, NH2-CH2-CH2-CH2-CH2-NH-C(-NH2)(=NH)) is the decarboxylation product of the amino acid arginine and is an intermediate in polyamine biosynthesis. It is a putative neurotransmitter. It is synthesized in the brain, stored in synaptic vesicles, accumulated by uptake, released by membrane depolarization, and inactivated by agmatinase. Agmatine binds to 2-adrenergic receptor and imidazoline binding sites, and blocks NMDA receptors and other cation ligand-gated channels. Agmatine inhibits nitric oxide synthase (NOS), and induces the release of some peptide hormones. Treatment with exogenous agmatine exerts neuroprotective effects in animal models of neurotrauma. -- Wikipedia; Agmatine ((4-aminobutyl)guanidine, NH2-CH2-CH2-CH2-CH2-NH-C(-NH2)(=NH)) is the decarboxylation product of the amino acid arginine and is an intermediate in polyamine biosynthesis. It is discussed as a putative neurotransmitter. It is synthesized in the brain, stored in synaptic vesicles, accumulated by uptake, released by membrane depolarization, and inactivated by agmatinase. Agmatine binds to ?2-adrenergic receptor and imidazoline binding sites, and blocks NMDA receptors and other cation ligand-gated channels. Agmatine inhibits nitric oxide synthase (NOS), and induces the release of some peptide hormones.
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