14923-17-2

Usage

Uses

Arcaine sulfate is a novel and potent antagonist of the polyamine site on the NMDA receptor.

Biological Activity

NO synthase inhibitor. An NMDA antagonist acting as a competitive inhibitor at the polyamine site.

InChI:InChI=1/C6H16N6.H2O4S/c7-5(8)11-3-1-2-4-12-6(9)10;1-5(2,3)4/h1-4H2,(H4,7,8,11)(H4,9,10,12);(H2,1,2,3,4)

Upstream product

• 14527-26-5 2-methylisothiourea sulphate 
• 110-60-1 1,4-diaminobutane 
• 867-44-7 S-Methylisothiourea sulfate 

Relevant academic research and scientific papers

Synthesis and pharmacology of alkanediguanidinium compounds that block the neuronal nicotinic acetylcholine receptor

Taking as models the polyamine toxin fraction FTX from the funnel-web spider venom, and the guanidinium moiety of guanethidine, a series of azaalkane-1,ω-diguanidinium salts were obtained. Some of them blocked ion fluxes through the neuronal nicotinic receptors for acetylcholine (nAChR). The blockade was exerted at submicromolar concentrations, suggesting a highly selective interaction with the nAChR. In fact, the active compounds on the nAChR ion channel did not recognize the voltage-dependent Na+ or Ca2+ channels of bovine adrenal chromaffin cells. Therefore, these compounds may be useful tools to clarify the functions of nAChR receptors in the central and peripheral nervous systems.

Benzylguanidines and other galegine analogues inducing weight loss in mice

Dimethylallylguanidine, also known as galegine, isolated from Galega officinalis, has been shown to have weight reducing properties in vivo. Substitution of the guanidine group with an N-cyano group and replacement of guanidine with amidine, pyrimidine, pyridine, or the imidazole moieties removed the weight reducing properties when evaluated in BALB/c mice. However, retention of the guanidine and replacement of the dimethylallyl group by a series of functionalized benzyl substituents was shown to exhibit, and in some cases significantly improve, the weight reducing properties of these molecules in BALB/c, ob/ob, and diet induced obesity (DIO) mice models. The lead compound identified, across all models, was 1-(4-chlorobenzyl)guanidine hemisulfate, which gave an average daily weight difference (% from time-matched controls; ± SEM) of -19.7 ± 1.0, -11.0 ± 0.7, and -7.3 ± 0.8 in BALB/c, ob/ob, and DIO models, respectively.