AGMATINE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H14N4
Molecular Weight	130.1915
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCCCNC(N)=N

InChI

InChIKey=QYPPJABKJHAVHS-UHFFFAOYSA-N

InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9)

HIDE SMILES / InChI

Molecular Formula	C5H14N4
Molecular Weight	130.1915
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Potency
Nitric-oxide synthase, brain 24 Target ID: CHEMBL3048 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8645212	Inhibitor 8504	660.0 µM [Ki]
Nitric oxide synthase, inducible 55 Target ID: CHEMBL3464 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8645212	Inhibitor 8504	220.0 µM [Ki]
Nitric-oxide synthase, endothelial 19 Target ID: CHEMBL4802 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8645212	Inhibitor 8504	7.5 mM [Ki]

PubMed

Title	Date	PubMed
A new class of N-hydroxycinnamoyltransferases. Purification, cloning, and expression of a barley agmatine coumaroyltransferase (EC 2.3.1.64).	2003-04-18	12582168
Arginine deprivation, growth inhibition and tumour cell death: 2. Enzymatic degradation of arginine in normal and malignant cell cultures.	2003-02-24	12592378
Molecular cloning of the gene for edeine B1 amidinohydrolase in addition to the agmatinase activity in Bacillus subtilis.	2003-02	12576691
Polyamine transport, accumulation, and release in brain.	2003-02	12558981
An in vivo evaluation of the antiseizure activity and acute neurotoxicity of agmatine.	2003-02	12543244
Agmatine is efficiently transported by non-neuronal monoamine transporters extraneuronal monoamine transporter (EMT) and organic cation transporter 2 (OCT2).	2003-02	12538837
Agmatine modulates the in vivo biosynthesis and interconversion of polyamines and cell proliferation.	2003-01-20	12527112
Effect of agmatine on intracellular free calcium concentration in isolated rat ventricular myocytes.	2002-12-25	12506317
Odor-stimulated glutamatergic neurotransmission in the zebrafish olfactory bulb.	2002-12-16	12442320
Agmatine inhibits arginine vasopressin-stimulated urea transport in the rat inner medullary collecting duct.	2002-12	12427134
Regulation of urea synthesis by agmatine in the perfused liver: studies with 15N.	2002-12	12388162
Comparison of a capillary electrophoresis method with high-performance liquid chromatography for the determination of biogenic amines in various food samples.	2002-11-05	12361737
Clonidine displacement from type 1 imidazoline receptor by p-aminobenzamidine, the prototype of trypsin-like serine protease inhibitors.	2002-11	12587981
I. Arginine.	2002-11	12481980
The metabolic basis of arginine nutrition and pharmacotherapy.	2002-11	12481979
Insights into the reaction mechanism of Escherichia coli agmatinase by site-directed mutagenesis and molecular modelling.	2002-11	12423350
Pheromonal activation of vomeronasal neurons in plethodontid salamanders.	2002-10-18	12376197
Radioligand binding studies reveal agmatine is a more selective antagonist for a polyamine-site on the NMDA receptor than arcaine or ifenprodil.	2002-10-11	12363406
Agmatine suppresses nitric oxide production and attenuates hypoxic-ischemic brain injury in neonatal rats.	2002-10	12357058
Synthesis and characterization of biodegradable cationic poly(propylene fumarate-co-ethylene glycol) copolymer hydrogels modified with agmatine for enhanced cell adhesion.	2002-09-10	12217050
Agmatine facilitates memory of an inhibitory avoidance task in adult rats.	2002-09	12431430
Effect of chronic morphine treatment on the biosynthesis of agmatine in rat brain and other tissues.	2002-08-23	12137915
Mapping photoreceptor and postreceptoral labelling patterns using a channel permeable probe (agmatine) during development in the normal and RCS rat retina.	2002-08-16	12180860
Synthesis of microcin SF608.	2002-07-12	12098309
[Imidazoline receptors-normal and pathological factors].	2002-07-03	12092170
[Interactions between liposomes and synaptosomes].	2002-07-03	12092138
Effects of agmatine on the escalation of intravenous cocaine and fentanyl self-administration in rats.	2002-07	12062577
Methanococcus jannaschii uses a pyruvoyl-dependent arginine decarboxylase in polyamine biosynthesis.	2002-06-28	11980912
Learning and memory in agmatine-treated rats.	2002-06	12175451
Exposure of rat isolated stomach and rats in vivo to [(14)C]agmatine: accumulation in the stomach wall and distribution in various tissues.	2002-06	12165069
Expression of the liver form of arginase in erythrocytes.	2002-06	12083807
Involvement of polyamines in root development at low temperature in the subantarctic cruciferous species Pringlea antiscorbutica.	2002-06	12021294
I(2)-imidazoline binding site affinity of a structurally different type of ligands.	2002-05	11886814
Quantitation of polyamines in hypothalamus and pituitary of female and male developing rats.	2002-04-19	11911991
Evidence for endogenous agmatine in hypothalamo-neurohypophysial tract and its modulation on vasopressin release and Ca2+ channels.	2002-04-05	11911858
Effects of NG-nitro-L-arginine methyl ester, 7-nitro indazole, and agmatine on pentylenetetrazol-induced discriminative stimulus in Long-Evans rats.	2002-04	11999909
Effects of polyamines on the release of gonadotropin-releasing hormone and gonadotropins in developing female rats.	2002-04	11910050
Agmatine produces antidepressant-like effects in two models of depression in mice.	2002-03-25	11930146
Sensory, chemical and bacteriological changes in vacuum-packed pressurised squid mantle (Todaropsis eblanae) stored at 4 degrees C.	2002-03-25	11929163
Behavior and characteristics of amine derivatives obtained with o-phthaldialdehyde/3-mercaptopropionic acid and with o-phthaldialdehyde/N-acetyl-L-cysteine reagents.	2002-03-08	11999740
Amino acid odorants stimulate microvillar sensory neurons.	2002-03	11923189
Effect of agmatine on L-type calcium current in rat ventricular myocytes.	2002-03	11918845
Cloning and characterization of human agmatinase.	2002-03	11914032
Characterization of the discriminable stimulus produced by 2-BFI: effects of imidazoline I(2)-site ligands, MAOIs, beta-carbolines, agmatine and ibogaine.	2002-03	11877331
Effect of agmatine on locus coeruleus neuron activity: possible involvement of nitric oxide.	2002-03	11877321
[Electrophysiological effects of phytoestrogen genistein on guinea pig papillary muscles].	2002-02-25	11930248
[The arginine paradox].	2002-01	11862757
Inhibition by apple polyphenols of ADP-ribosyltransferase activity of cholera toxin and toxin-induced fluid accumulation in mice.	2002	12061627
Sensory, chemical and bacteriological changes during storage of iced squid (Todaropsis eblanae).	2002	11972700
Differential responses of regional vascular beds to local injection of agmatine in rats.	2001-12	11930224

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:15:36 GMT 2025` Edited by `admin` on `Mon Mar 31 19:15:36 GMT 2025`
Record UNII	70J407ZL5Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AGMATINE

Systematic Name

English

NSC-56332

Preferred Name

English

Agmatine [WHO-DD]

Common Name

English

1-AMINO-4-GUANIDOBUTANE

Common Name

English

AGMATINE [MI]

Common Name

English

GUANIDINE, (4-AMINOBUTYL)-

Systematic Name

English

N-(4-AMINOBUTYL)GUANIDINE

Systematic Name

English

Classification Tree Code System Code

DSLD

3255 (Number of products:364)