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Norscopolamine

CAS# 4684-28-0

Norscopolamine

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Chemical structure

Norscopolamine

3D structure

Chemical Properties of Norscopolamine

Cas No. 4684-28-0 SDF Download SDF
PubChem ID 92989 Appearance White powder
Formula C16H19NO4 M.Wt 289.3
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Norhyoscine
Solubility Soluble in acetone, chloroform and DMSO
Chemical Name [(1S,2S,4R,5R)-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-3-hydroxy-2-phenylpropanoate
SMILES C1C(CC2C3C(C1N2)O3)OC(=O)C(CO)C4=CC=CC=C4
Standard InChIKey MOYZEMOPQDTDHA-LACSLYJWSA-N
Standard InChI InChI=1S/C16H19NO4/c18-8-11(9-4-2-1-3-5-9)16(19)20-10-6-12-14-15(21-14)13(7-10)17-12/h1-5,10-15,17-18H,6-8H2/t10?,11-,12-,13+,14-,15+/m1/s1
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 Norscopolamine

The herbs of Atropanthe sinensis

Protocol of Norscopolamine

Structure Identification
Green Chemistry, 2012, 14(4):1189-1195.

One-pot oxidative N-demethylation of tropane alkaloids with hydrogen peroxide and a FeIII-TAML catalyst.[Reference: WebLink]


METHODS AND RESULTS:
The oxidative N-demethylation of tropane alkaloids to their nortropane derivatives has been investigated using H2O2 and an iron(III) tetraamido macrocycle (FeIII-TAML) catalyst. The yields of the nortropanes were found to be dependent on the amount of H2O2 used in the reaction, the catalyst loading, the nature of the organic co-solvent and the type of tropine substrate. N-Hydroxy-nortropane, N-formyl-nortropane and tropane-N-oxide derivatives were identified as by-products of the reaction.
CONCLUSIONS:
After screening various reaction conditions, the optimised conditions were applied to the N-demethylation of atropine and scopolamine at preparative scales and the desired products, noratropine and Norscopolamine, obtained following one pot reactions in good yields and high purity without the need for any chromatographic purification steps.

Norscopolamine Dilution Calculator

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Norscopolamine Molarity Calculator

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Preparing Stock Solutions of Norscopolamine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.4566 mL 17.2831 mL 34.5662 mL 69.1324 mL 86.4155 mL
5 mM 0.6913 mL 3.4566 mL 6.9132 mL 13.8265 mL 17.2831 mL
10 mM 0.3457 mL 1.7283 mL 3.4566 mL 6.9132 mL 8.6415 mL
50 mM 0.0691 mL 0.3457 mL 0.6913 mL 1.3826 mL 1.7283 mL
100 mM 0.0346 mL 0.1728 mL 0.3457 mL 0.6913 mL 0.8642 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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References on Norscopolamine

Simple interface for scanning chemical compounds on developed thin layer chromatography plates using electrospray ionization mass spectrometry.[Pubmed:30612639]

Anal Chim Acta. 2019 Feb 21;1049:1-9.

A simple and cheap design for interfacing thin layer chromatography (TLC) with electrospray ionization mass spectrometry (ESI/MS) was developed to scan and characterize compounds on TLC plate. The developed TLC plate was rapidly and easily modified into two sawtooth-edged pieces that were positioned on an XYZ stage so that one of the triangular tips was pointed toward the MS inlet. A drop of methanol and high DC voltage was applied at the tip to induce ESI. After the analytes in the first tip were analyzed, the TLC piece was moved so that the second triangular tip was pointed toward the MS inlet for analysis. The process was repeated until all the triangular tips on the piece were analyzed. In this manner, the analytes, no matter visible or non-visible bands, were scanned and characterized. Since a 4.8cm long TLC track were cut to 32 triangles on two sawtooth pieces for analysis, the spatial resolution of using the sawtooth TLC-ESI/MS for analysis is 1.5 mm/band. A mixture of dye standards and Datura metel flower extract was analyzed to demonstrate the capability of sawtooth TLC-ESI/MS on scanning and characterizing chemical compounds on the TLC plates. The limits of detection of the dye standards were between 0.25 and 2.5 ng/band. TLC bands containing alkaloids such as scopolamine and Norscopolamine from the Datura metel flower extract were not visualized on the developed TLC track, but were successfully detected at different triangular tips using sawtooth TLC-ESI/MS. Based on these results, the Rf values of scopolamine and Norscopolamine were determined.

Analysis of scopolamine and its eighteen metabolites in rat urine by liquid chromatography-tandem mass spectrometry.[Pubmed:18970269]

Talanta. 2005 Oct 31;67(5):984-91.

A rapid and sensitive method is described for the determination of scopolamine and its metabolites in rat urine by combining liquid chromatography and tandem mass spectrometry (LC-MS/MS). Various extraction techniques (free fraction, acid hydrolyses and enzyme hydrolyses) and their comparison were carried out for investigation of the metabolism of scopolamine. After extraction procedure, the pretreated samples were injected into a reversed-phase C18 column with mobile phase of methanol/ ammonium acetate (2mM, adjusted to pH 3.5 with formic acid) (70:30, v/v) and detected by an on-line MS/MS system. Identification and structural elucidation of the metabolites were performed by comparing their changes in molecular masses (DeltaM), retention-times and full scan MS(n) spectra with those of the parent drug. The results revealed that at least 18 metabolites (norscopine, scopine, tropic acid, apoNorscopolamine, aposcopolamine, Norscopolamine, hydroxyscopolamine, hydroxyscopolamine N-oxide, p-hydroxy-m-methoxyscopolamine, trihydroxyscopolamine, dihydroxy-methoxyscopolamine, hydroxyl-dimethoxyscopolamine, glucuronide conjugates and sulfate conjugates of Norscopolamine, hydroxyscopolamine and the parent drug) and the parent drug existed in urine after ingesting 55mg/kg scopolamine to healthy rats. Hydroxyscopolamine, p-hydroxy-m-methoxyscopolamine and the parent drug were detected in rat urine for up 106h after ingestion of scopolamine.

Liquid chromatography-electrospray ionization ion trap mass spectrometry for analysis of in vivo and in vitro metabolites of scopolamine in rats.[Pubmed:18218192]

J Chromatogr Sci. 2008 Jan;46(1):74-80.

In vivo and in vitro metabolism of scopolamine is investigated using a highly specific and sensitive liquid chromatography-mass spectrometry (LC-MSn) method. Feces, urine, and plasma samples are collected individually after ingestion of 55 mg/kg scopolamine by healthy rats. Rat feces and urine samples are cleaned up by a liquid-liquid extraction and a solid-phase extraction procedure (C18 cartridges), respectively. Methanol is added to rat plasma samples to precipitate plasma proteins. Scopolamine is incubated with homogenized liver and intestinal flora of rats in vitro, respectively. The metabolites in the incubating solution are extracted with ethyl acetate. Then these pretreated samples are injected into a reversed-phase C18 column with mobile phase of methanol-ammonium acetate (2 mM, adjusted to pH 3.5 with formic acid) (70:30, v/v) and detected by an on-line MSn system. Identification and structural elucidation of the metabolites are performed by comparing their changes in molecular masses (DeltaM), retention-times and full scan MSn spectra with those of the parent drug. The results reveal that at least 8 metabolites (norscopine, scopine, tropic acid, apoNorscopolamine, aposcopolamine, Norscopolamine, hydroxyscopolamine, and hydroxyscopolamine N-oxide) and the parent drug exist in feces after administering 55 mg/kg scopolamine to healthy rats. Three new metabolites (tetrahydroxyscopolamine, trihydroxy-methoxyscopolamine, and dihydroxy-dimethoxyscopolamine) are identified in rat urine. Seven metabolites (norscopine, scopine, tropic acid, apoNorscopolamine, aposcopolamine, Norscopolamine, and hydroxyscopolamine) and the parent drug are detected in rat plasma. Only 1 hydrolyzed metabolite (scopine) is found in the rat intestinal flora incubation mixture, and 2 metabolites (aposcopolamine and Norscopolamine) are identified in the homogenized liver incubation mixture.

Metabolism in vivo of the tropane alkaloid, scopolamine, in several mammalian species.[Pubmed:1796606]

Xenobiotica. 1991 Oct;21(10):1289-300.

1. In vivo metabolism of scopolamine was studied in rats, mice, guinea pigs and rabbits. The structures of eight urinary metabolites including unchanged drug were elucidated by mass and nuclear magnetic resonance spectrometry. Determination of these metabolites was achieved by a g.l.c. method using a semi-capillary column. 2. The major metabolites in rats were the three phenolic metabolites, p-hydroxy-, m-hydroxy- and p-hydroxy-m-methoxy-scopolamine. 3. Significant intra-species difference of the metabolism was observed in rabbits. Tropic acid was the major metabolite in two rabbits out of three, while the other rabbit excreted mainly unchanged scopolamine, accompanied by five metabolites. Tropic acid was also the major metabolite in guinea pigs, but was of minor importance in mice. 4. The dehydrated metabolites, aposcopolamine and apoNorscopolamine, were abundantly excreted in guinea pigs, moderately in mice, and least in rabbits and rats. 5. Excretion of glucuronide conjugates of scopolamine and Norscopolamine were high in mice compared with other species. On the other hand, phenolic metabolites in rat urine; and tropic acid in rabbit and guinea pig urine, were excreted as the free forms. 6. These results indicate that scopolamine metabolism is highly species-specific.

Routine synthesis of N-[11C-methyl]scopolamine by phosphite mediated reductive methylation with [11C]formaldehyde.[Pubmed:2840412]

Int J Rad Appl Instrum A. 1988;39(5):373-9.

A synthesis of [11C]scopolamine capable of clinical delivery of this agent in high specific activity is described. The precursor [11C]formaldehyde was produced by catalytic oxidation of [11C]CH3OH over metallic silver and was used to N-11C-methylate Norscopolamine using aqueous neutral potassium phosphite as the reducing agent. The labeling reaction was complete after 5 min at 75-80 degrees C and the [11C]scopolamine (99% radiochemical purity) was isolated by preparative HPLC. Total synthesis time is less than 45 min. Decay corrected radiochemical yields from [11C]CO2 are presently 20-43%.

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