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N-Demethyl-alpha-obscurine

CAS# 34399-44-5

N-Demethyl-alpha-obscurine

Catalog No. BCN7362----Order now to get a substantial discount!

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Quality Control of N-Demethyl-alpha-obscurine

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Chemical structure

N-Demethyl-alpha-obscurine

3D structure

Chemical Properties of N-Demethyl-alpha-obscurine

Cas No. 34399-44-5 SDF Download SDF
PubChem ID 46218452 Appearance Powder
Formula C16H24N2O M.Wt 260.38
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC1CC2CC3=C(CCC(=O)N3)C4(C1)C2CCCN4
Standard InChIKey SODGYLLKKFRBQO-AZKPJATDSA-N
Standard InChI InChI=1S/C16H24N2O/c1-10-7-11-8-14-13(4-5-15(19)18-14)16(9-10)12(11)3-2-6-17-16/h10-12,17H,2-9H2,1H3,(H,18,19)/t10-,11+,12-,16-/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 N-Demethyl-alpha-obscurine

The whole plants of Lycopodium japonicum.

Biological Activity of N-Demethyl-alpha-obscurine

DescriptionN-Demethyl-alpha-obscurine is a natural product from Lycopodium japonicum.
In vitro

Lycopodium alkaloids from Lycopodium japonicum.[Reference: WebLink]

Chinese Traditional & Herbal Drugs, 2015, 46(9):1269-1276.

To study the chemical constituents in the whole herb of Lycopodium japonicum.
METHODS AND RESULTS:
The constituents were isolated and purified by silica gel and semi-preparative HPLC, and their structures were elucidated by means of physicochemical properties and spectroscopic analysis. All the isolated compounds were evaluated using relevant in vitro anti-inflammatory assay against LPS-induced NO releases.Nineteen compounds were isolated from the whole herb of L. japonicum, and identified as lycoposerramine-M N-oxide (1), acetyllycoposerramine-M (2), lycopodine (3), lycoposerramine-M (4), miyoshianine-C (5), 12-epilycodoline N-oxide (6), gnidioidine (7), lycoposerramine-K (8), lucidioline (9), 4α-hydroxyanhydrolycodoline (10), flabelline (11), hydroxypropyllycodine (12), lycodine (13), des-N-methyl-α-obscurine (N-Demethyl-alpha-obscurine,14), α-obscurine (15), des-N-methyl-β-obscurine (16), lycoflexine (17), lycoflexine N-oxide (18), and fawcettidine (19). Compound 5 and 18 could inhibit the release of nitric oxide (NO) in the RAW264.7 cell line stimulated by lipopolysaccaride. The IC50 values of 5 and 18 are 31.82 and 40.69 μmol/L, respectively.
CONCLUSIONS:
Compound 1 is a new compound, named lycoposerramine-M N-oxide, compounds 2, 6, 11, 12, 16, 18, and 19 are isolated from this plant for the first time. Compounds 5 and 18 exhibit the potent inhibitory activity.

Protocol of N-Demethyl-alpha-obscurine

Structure Identification
European Journal of Organic Chemistry, 1983, 1983(2):220-225.

Synthese desLycopodium-Alkaloidsrac-α-Obscurin durch 1,3-Anellierung eines Enimins.[Reference: WebLink]


METHODS AND RESULTS:
Synthesis of the Lycopodium-Alkaloids rac-α-Obscurin through 1,3-Anullation of an Enimine Acid catalysed 1,3-annulation of 1,2,3,4-tetrahydro-6-methyl-2-oxopyridine (1) to the enimine 3, followed by methylation, provides a new regio and stereoselective route to rac-α-obscurine (5). Reduction of rac-N-Demethyl-alpha-obscurine with LiAlH4 yields rac-lycodine (11) and rac-deacetyl-flabellidine (9).
CONCLUSIONS:
A new pathway for the biogenesis of the β-amino-imine 9 is suggested.

N-Demethyl-alpha-obscurine Dilution Calculator

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N-Demethyl-alpha-obscurine Molarity Calculator

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Preparing Stock Solutions of N-Demethyl-alpha-obscurine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.8405 mL 19.2027 mL 38.4054 mL 76.8108 mL 96.0135 mL
5 mM 0.7681 mL 3.8405 mL 7.6811 mL 15.3622 mL 19.2027 mL
10 mM 0.3841 mL 1.9203 mL 3.8405 mL 7.6811 mL 9.6014 mL
50 mM 0.0768 mL 0.3841 mL 0.7681 mL 1.5362 mL 1.9203 mL
100 mM 0.0384 mL 0.192 mL 0.3841 mL 0.7681 mL 0.9601 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 N-Demethyl-alpha-obscurine

Lycopodium alkaloids from Lycopodium japonicum.

Chinese Traditional & Herbal Drugs, 2015, 46(9):1269-1276.

To study the chemical constituents in the whole herb of Lycopodium japonicum. Methods: The constituents were isolated and purified by silica gel and semi-preparative HPLC, and their structures were elucidated by means of physicochemical properties and spectroscopic analysis. All the isolated compounds were evaluated using relevant in vitro anti-inflammatory assay against LPS-induced NO releases. Results: Nineteen compounds were isolated from the whole herb of L. japonicum, and identified as lycoposerramine-M N-oxide (1), acetyllycoposerramine-M (2), lycopodine (3), lycoposerramine-M (4), miyoshianine-C (5), 12-epilycodoline N-oxide (6), gnidioidine (7), lycoposerramine-K (8), lucidioline (9), 4α-hydroxyanhydrolycodoline (10), flabelline (11), hydroxypropyllycodine (12), lycodine (13), des-N-methyl-α-obscurine (N-Demethyl-alpha-obscurine,14), α-obscurine (15), des-N-methyl-β-obscurine (16), lycoflexine (17), lycoflexine N-oxide (18), and fawcettidine (19). Compound 5 and 18 could inhibit the release of nitric oxide (NO) in the RAW264.7 cell line stimulated by lipopolysaccaride. The IC50 values of 5 and 18 are 31.82 and 40.69 μmol/L, respectively. Conclusion: Compound 1 is a new compound, named lycoposerramine-M N-oxide, compounds 2, 6, 11, 12, 16, 18, and 19 are isolated from this plant for the first time. Compounds 5 and 18 exhibit the potent inhibitory activity. ©, 2015, Editorial Office of Chinese Traditional and Herbal Drugs.

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