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

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 8297	660.0 µM [Ki]
Nitric oxide synthase, inducible 50 Target ID: CHEMBL3464 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8645212	Inhibitor 8297	220.0 µM [Ki]
Nitric-oxide synthase, endothelial 19 Target ID: CHEMBL4802 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8645212	Inhibitor 8297	7.5 mM [Ki]

PubMed

Title	Date	PubMed
Characterization of spermine uptake by Ehrlich tumour cells in culture.	2001	11764408
Inhibition of pig liver and Zea mays L. polyamine oxidase: a comparative study.	2001	11342283
Polyamines of the thermophilic eubacteria belonging to the genera Thermosipho, Thermaerobacter and Caldicellulosiruptor.	2001	11327112
[Agmatine inhibits the afferent activity of carotid baroreceptor in rats].	2001 Apr	11471214
Blockade by agmatine of catecholamine release from chromaffin cells is unrelated to imidazoline receptors.	2001 Apr 6	11301064
Novel hypotensive agents from Verbesina caracasana. 8. Synthesis and pharmacology of (3,4-dimethoxycinnamoyl)-N(1)-agmatine and synthetic analogues.	2001 Aug 30	11520203
Differential responses of regional vascular beds to local injection of agmatine in rats.	2001 Dec	11930224
Isolation and properties of arginase from a shade plant, ginseng (Panax ginseng C.A. Meyer) roots.	2001 Dec	11730864
The effect of agmatine administration on ischemic-reperfused isolated rat heart.	2001 Jan	11452335
[Interactions between liposomes and synaptosomes].	2001 Jan-Mar	12092138
Down-regulation of MAO-B activity and imidazoline receptors in rat brain following chronic treatment of morphine.	2001 Jul	11749830
Biological significance of agmatine, an endogenous ligand at imidazoline binding sites.	2001 Jul	11454649
Differential expression of the cationic amino acid transporter 2(B) in the adult rat brain.	2001 Jul 13	11457509
[Imidazoline receptors-normal and pathological factors].	2001 Jul-Sep	12092170
Growth and metabolic activity of Shewanella putrefaciens maintained under different CO2 and O2 concentrations.	2001 Mar 20	11294349
Morphine and clonidine activate different K+ channels on rat amygdala neurons.	2001 Mar 9	11245859
Agmatine produces antinociception in tonic pain in mice.	2001 May-Jun	11420073
Opposite effects of low and high doses of arginine on glutamate-induced nitric oxide formation in rat substantia nigra.	2001 Nov 16	11704300
Effects of polyamines on the release of gonadotropin-releasing hormone and gonadotropins in developing female rats.	2002 Apr	11910050
Evidence for endogenous agmatine in hypothalamo-neurohypophysial tract and its modulation on vasopressin release and Ca2+ channels.	2002 Apr 5	11911858
Effect of chronic morphine treatment on the biosynthesis of agmatine in rat brain and other tissues.	2002 Aug 23	12137915
Agmatine inhibits arginine vasopressin-stimulated urea transport in the rat inner medullary collecting duct.	2002 Dec	12427134
Regulation of urea synthesis by agmatine in the perfused liver: studies with 15N.	2002 Dec	12388162
Odor-stimulated glutamatergic neurotransmission in the zebrafish olfactory bulb.	2002 Dec 16	12442320
Effect of agmatine on intracellular free calcium concentration in isolated rat ventricular myocytes.	2002 Dec 25	12506317
Agmatine oxidation by copper amine oxidase.	2002 Feb	11846789
Cloning of human agmatinase. An alternate path for polyamine synthesis induced in liver by hepatitis B virus.	2002 Feb	11804860
Noradrenaline release-inhibiting receptors on PC12 cells devoid of alpha(2(-)) and CB(1) receptors: similarities to presynaptic imidazoline and edg receptors.	2002 Feb	11738482
[The arginine paradox].	2002 Jan	11862757
Molecular phenotyping of retinal ganglion cells.	2002 Jan 15	11784786
Agmatine: a mastoparan-like activity related to direct activation of heterotrimeric G proteins.	2002 Jan 18	11790374
Mapping photoreceptor and postreceptoral labelling patterns using a channel permeable probe (agmatine) during development in the normal and RCS rat retina.	2002 Jan-Feb	12180860
Effects of agmatine on the escalation of intravenous cocaine and fentanyl self-administration in rats.	2002 Jul	12062577
Synthesis of microcin SF608.	2002 Jul 12	12098309
Learning and memory in agmatine-treated rats.	2002 Jun	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 Jun	12165069
Expression of the liver form of arginase in erythrocytes.	2002 Jun	12083807
Methanococcus jannaschii uses a pyruvoyl-dependent arginine decarboxylase in polyamine biosynthesis.	2002 Jun 28	11980912
Cloning and characterization of human agmatinase.	2002 Mar	11914032
Effect of agmatine on locus coeruleus neuron activity: possible involvement of nitric oxide.	2002 Mar	11877321
Agmatine produces antidepressant-like effects in two models of depression in mice.	2002 Mar 25	11930146
Clonidine displacement from type 1 imidazoline receptor by p-aminobenzamidine, the prototype of trypsin-like serine protease inhibitors.	2002 Nov	12587981
I. Arginine.	2002 Nov	12481980
The metabolic basis of arginine nutrition and pharmacotherapy.	2002 Nov	12481979
Insights into the reaction mechanism of Escherichia coli agmatinase by site-directed mutagenesis and molecular modelling.	2002 Nov	12423350
Comparison of a capillary electrophoresis method with high-performance liquid chromatography for the determination of biogenic amines in various food samples.	2002 Nov 5	12361737
Pheromonal activation of vomeronasal neurons in plethodontid salamanders.	2002 Oct 18	12376197
A new class of N-hydroxycinnamoyltransferases. Purification, cloning, and expression of a barley agmatine coumaroyltransferase (EC 2.3.1.64).	2003 Apr 18	12582168
Arginine deprivation, growth inhibition and tumour cell death: 2. Enzymatic degradation of arginine in normal and malignant cell cultures.	2003 Feb 24	12592378
Agmatine modulates the in vivo biosynthesis and interconversion of polyamines and cell proliferation.	2003 Jan 20	12527112

Patents

Name

Type

Language

AGMATINE

Systematic 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

NSC-56332

Code

English

N-(4-AMINOBUTYL)GUANIDINE

Systematic Name

English

Classification Tree Code System Code

DSLD

3255 (Number of products:364)