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Norarecoline hydrochloride

CAS# 6197-39-3

Norarecoline hydrochloride

Catalog No. BCN8401----Order now to get a substantial discount!

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Norarecoline hydrochloride: 5mg $52 In Stock
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Quality Control of Norarecoline hydrochloride

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Chemical structure

Norarecoline hydrochloride

3D structure

Chemical Properties of Norarecoline hydrochloride

Cas No. 6197-39-3 SDF Download SDF
PubChem ID 201540 Appearance White crystalline powder
Formula C7H12ClNO2 M.Wt 177.629
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Guvacine methyl ester hydrochloride; Norarecoline hydrochloride
Solubility Soluble in ethanol and water; slightly soluble in chloroform and diethyl ether
Chemical Name methyl 1,2,3,6-tetrahydropyridine-5-carboxylate;hydrochloride
SMILES COC(=O)C1=CCCNC1.Cl
Standard InChIKey ZWALOEQHJRUTKM-UHFFFAOYSA-N
Standard InChI InChI=1S/C7H11NO2.ClH/c1-10-7(9)6-3-2-4-8-5-6;/h3,8H,2,4-5H2,1H3;1H
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Norarecoline hydrochloride

The fruits of Areca catechu

Biological Activity of Norarecoline hydrochloride

DescriptionNorarecoline is a muscarinic agonist.
In vitro

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]

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

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.

Protocol of Norarecoline hydrochloride

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.

Norarecoline hydrochloride Dilution Calculator

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Norarecoline hydrochloride Molarity Calculator

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Preparing Stock Solutions of Norarecoline hydrochloride

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.6297 mL 28.1486 mL 56.2971 mL 112.5942 mL 140.7428 mL
5 mM 1.1259 mL 5.6297 mL 11.2594 mL 22.5188 mL 28.1486 mL
10 mM 0.563 mL 2.8149 mL 5.6297 mL 11.2594 mL 14.0743 mL
50 mM 0.1126 mL 0.563 mL 1.1259 mL 2.2519 mL 2.8149 mL
100 mM 0.0563 mL 0.2815 mL 0.563 mL 1.1259 mL 1.4074 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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