498-96-4

Usage

Uses

Used in Pharmaceutical Industry:
Guvacine Hydrochloride is used as a GABA uptake inhibitor for its potential role in treating neuropsychiatric disorders. By inhibiting the reuptake of GABA, it can help maintain higher levels of this neurotransmitter in the brain, which may contribute to the alleviation of symptoms associated with these disorders.
Used in Neurochemistry Research:
In the field of neurochemistry, Guvacine Hydrochloride is used as a research tool to study the function and regulation of GABA transporters. Understanding the interactions between Guvacine Hydrochloride and these transporters can provide valuable insights into the mechanisms underlying various neuropsychiatric conditions and guide the development of novel therapeutic strategies.

Biological Activity

Specific GABA uptake inhibitor. IC 50 values are 14, 58, 119 and 1870 mM for hGAT-1, rGAT-2, hGAT-3 and hBGT-1 respectively.

InChI:InChI=1/C6H9NO2/c8-6(9)5-2-1-3-7-4-5/h2,7H,1,3-4H2,(H,8,9)

Upstream product

• 59-67-6 nicotinic acid 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 5435-00-7 1-benzoyl-4-hydroxy-piperidine-3-carboxylic acid ethyl ester 
• 3518-88-5 3,3'-imino-di-propionic acid diethyl ester 
• 121661-86-7 (N-chlorocarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester) 
• 300-08-3 arecoline hydrobromide 
• 7664-93-9 sulfuric acid 
• 17210-51-4 1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester hydrobromide 
• 63-75-2 arecoline 
• 495-19-2 norarecoline 
• 92600-27-6 1-(1-chloroethyl) 3-methyl 5,6-dihydropyridine-1,3(2H)-dicarboxylate 
• 4451-86-9 ethyl 1-benzoyl-4-oxopiperidine-3-carboxylate 
• 101599-56-8 3,3'-benzoylimino-di-propionic acid diethyl ester 

Downstream Products

• 498-95-3 (R)-nipecotic acid 
• 309748-80-9 (R)-tert-butyl 3-(phenylcarbamoyl)piperidine-1-carboxylate 
• 211511-69-2 5-Bromomethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 126114-07-6 tert-butyl 5-(hydroxymethyl)-3,6-dihydro-1(2H)-pyridinecarboxylate 
• 86447-11-2 1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid 
• 498-95-3 nipecotic acid 
• 108-99-6 3-Methylpyridine 
• 189286-20-2 1-(ethoxycarbonyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid 

Relevant academic research and scientific papers

Discovery of potent iminoheterocycle BACE1 inhibitors

The synthesis of a series of iminoheterocycles and their structure-activity relationships (SAR) as inhibitors of the aspartyl protease BACE1 will be detailed. An effort to access the S3 subsite directly from the S1 subsite initially yielded compounds with sub-micromolar potency. A subset of compounds from this effort unexpectedly occupied a different binding site and displayed excellent BACE1 affinities. Select compounds from this subset acutely lowered Aβ40 levels upon subcutaneous and oral administration to rats.

Iridium-catalyzed enantioselective hydrogenation of unsaturated heterocyclic acids

Spiral binding: A highly enantioselective hydrogenation of unsaturated heterocyclic acids has been developed by using chiral iridium/spirophosphino oxazoline catalysts (see scheme; BArF-=tetrakis[3,5- bis(trifluoromethyl)phenyl]borate, Boc=tert-butoxycarbonyl). This reaction provided an efficient method for the preparation of optically active heterocyclic acids with excellent enantioselectivities. Copyright

USE OF NEUROPROTECTIVE COMPOUNDS IN OBTAINING MEDICAMENTS INTENDED FOR THE TREATMENT OF NEURODEGENERATING DISEASES

Use of neuroprotective compounds in obtaining medicaments intended for the curative treatment of neurodegenerative disease and/or the prevention of the appearance of disorders ensuing from those diseases.

Synthesis and muscarinic activity of a series of tertiary and quaternary N-substituted guvacine esters structurally related to arecoline and arecaidine propargyl ester

A series of tertiary and quaternary N-substituted guvacine (1,2,5,6-tetrahydro-3-carboxy-pyridine) methyl and propargyl esters have been synthesized and tested for muscarinic/antimuscarinic activity on rat ileum and electrically paced left atria. Arecoline and arecaidine propargyl ester (APE) as well as their corresponding N-demethyl derivatives, guvacoline (norarecoline) and guvacine propargyl ester, acted as full agonists at both atrial and ileal muscarinic receptors (range of pD2-values 6.09-8.07). However, in both preparations arecoline and APE were clearly more potent (up to 15-fold) than their N-demethyl analogues. Replacement of the N-methyl group in arecoline and APE by larger substituents (ethyl, n-propyl, n-butyl, benzyl, phenylethyl) as well as N-methylation resulted in a decrease or even a complete loss of agonistic activity. In both organs, the propargyl esters usually showed higher potency than the corresponding methyl ester analogues. N-Ethylguvacine propargyl ester and APE methiodide displayed pronounced agonistic activity in the atria (pD2 ? 6.5; intrinsic activity = 0.79 and 0.67, respectively) but behaved as competitive antagonists in the ileum (pA2 = 6.06 and 5.62, respectively). Beside the lower sensitivity to muscarinic agonists of the rat ileum as compared to rat atria, the cardioselective stimulant action of both agents may also be due to their ability to recognize structural differences between atrial M(2α) and ileal M(2β) muscarinic receptor subtypes.