Norarecoline Hydrochloride | CAS:6197-39-3

Norarecoline Hydrochloride

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Description:

Norarecoline is a muscarinic agonist.

In vitro:

Arzneimittelforschung. 1989 May;39(5):539-44.

Synthesis and muscarinic activity of a series of tertiary and quaternary N-substituted guvacine esters structurally related to arecoline and arecaidine propargyl ester.[Pubmed: 2757669]

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.
METHODS AND RESULTS:
Arecoline and arecaidine propargyl ester (APE) as well as their corresponding N-demethyl derivatives, guvacoline (norarecoline, Norarecoline Hydrochloride) 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.
CONCLUSIONS:
N-Ethylguvacine propargyl ester and APE methiodide displayed pronounced agonistic activity in the atria (pD2 approximately 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 M2 alpha and ileal M2 beta muscarinic receptor subtypes.

Norarecoline Hydrochloride Description

Source:	The fruits of Areca catechu
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Structure Identification:

Drug Des Discov. 1993;9(3-4):237-50.

Conformational aspects of the muscarinic receptor interactions of bicyclic isoxazole ester bioisosteres of arecoline.[Pubmed: 8400005]

METHODS AND RESULTS:
3-Methoxy-4,5,6,7-tetrahydroisoxazolo [4,5-c]pyridine (O-Me-THPO) and O,5-di-Me-THPO are conformationally restricted bioisosteres of the muscarinic agonists norarecoline(Norarecoline Hydrochloride ) and arecoline, respectively, showing partial agonist effects at muscarinic acetylcholine receptors. The 7-membered ring analogue of O-Me-THPO, 3-methoxy-5,6,7,8-tetrahydro-4H-isoxazolo[4,5-c]azepine (O-Me-THAO), shows higher affinity for muscarinic receptor sites than O-Me-THPO or O,5-di-Me-THPO. Similarly, O-Et-THAO binds much more tightly to muscarinic receptor sites than its 6-membered ring analogues, O-Et-THPO and O-Et-5-Me-THPO. Based on receptor binding data, O-Me-THPO and O-Me-THAO, and O-Et-THPO and O-Et-THAO, respectively, show similar degrees of partial agonism. They also show similar relative affinities for muscarinic M1 and M2 receptor sites. Using the semiempirical quantum mechanics programme, AM1, and the molecular mechanics programme, SYBYL, we have studied the conformational flexibility of the O-alkyl-THPO and O-alkyl-THAO ring systems.
CONCLUSIONS:
As expected, the 7-membered ring of the latter system was shown to be markedly more flexible than the piperidine rings of O-alkyl-THPO analogues. On the basis of this analysis, a common pharmacophore for these two classes of compounds was constructed.

Product Name	Norarecoline Hydrochloride
Price:
CAS No.:	6197-39-3
Catalog No.:	CFN93318
Molecular Formula:	C₇H₁₂ClNO₂
Molecular Weight:	177.62 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Powder
Source:	The fruits of Areca catechu
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS
Similar structural:	Comparison
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Alkaloids Compound Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	5.63 mL	28.15 mL	56.3 mL	112.5999 mL	140.7499 mL
5 mM	1.126 mL	5.63 mL	11.26 mL	22.52 mL	28.15 mL
10 mM	0.563 mL	2.815 mL	5.63 mL	11.26 mL	14.075 mL
50 mM	0.1126 mL	0.563 mL	1.126 mL	2.252 mL	2.815 mL
100 mM	0.0563 mL	0.2815 mL	0.563 mL	1.126 mL	1.4075 mL

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