17210-51-4

Basic information

• Product Name: Guvacoline Hydrobromide
• Synonyms: 1,2,5,6-Tetrahydro-3-pyridinecarboxylic Acid Methyl Ester HydrobroMide;1,2,5,6-tetrahydro-3-pyridinecarboxylic acid, methyl ester, monohydrobromide
• CAS NO: 17210-51-4
• Molecular Formula: BrH*C₇H₁₁NO₂
• Molecular Weight: 222.07968
• Product Categories: Amines;Heterocycles;Intermediates & Fine Chemicals;Nicotine Derivatives;Pharmaceuticals;Amines, Heterocycles, Nicotine Derivatives, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 17210-51-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 144°C
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: ≤1mg/ml in DMSO;1mg/ml in dimethyl formamide
• CAS DataBase Reference: Guvacoline Hydrobromide(CAS DataBase Reference)
• NIST Chemistry Reference: Guvacoline Hydrobromide(17210-51-4)
• EPA Substance Registry System: Guvacoline Hydrobromide(17210-51-4)

Safety Data

• Hazardous Substances Data: 17210-51-4(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Uses

A muscarinic receptor used as nootropic agent.

Biological Activity

guvacoline is a kind of natural alkaloid which is found in areca nuts that is related to the nootropic, arecoline. guvacoline can function as a full agonist of atrial and ileal muscarinic receptors.in vitro: in human buccal epithelial cells, guvacoline could significantly decrease the colony-formation efficiency in a dose dependent manner, with the ic50 value of 2.1 mm. besides, guvacoline could also dose-dependently reduce the amount of total free low-molecular-weight thiols (0.88 mm guvacoline caused 25% decrease) and increase the number of single strand breaks [1].

target

atrial and ileal muscarinic receptors

IC 50

2.1 mm for growth inhibition of human buccal epithelial cells

references

[1] k. sundqvist, y. liu, j. nair, et al. cytotoxic and genotoxic effects of areca nut-related compounds in cultured human buccal epithelial cells. cancer research 49(19), 5294-5298 (1989).

Upstream product

• 121661-86-7 (N-chlorocarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester) 
• 300-08-3 arecoline hydrobromide 

Downstream Products

• 100718-03-4 1-benzyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester; hydrobromide 
• 155394-42-6 N-ethyl-1,2,3,6-tetrahydropyridine-5-carboxylic acid 
• 498-96-4 guvacine 

Relevant articles and documents

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.