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(+)-Isoajmaline

CAS# 6989-79-3

(+)-Isoajmaline

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Chemical structure

(+)-Isoajmaline

3D structure

Chemical Properties of (+)-Isoajmaline

Cas No. 6989-79-3 SDF Download SDF
PubChem ID 251572 Appearance Powder
Formula C20H26N2O2 M.Wt 326.4
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1R,9R,10S,12S,13R,14S,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene-14,18-diol
SMILES CCC1C2CC3C4C5(CC(C2C5O)N3C1O)C6=CC=CC=C6N4C
Standard InChIKey CJDRUOGAGYHKKD-AVQYEUALSA-N
Standard InChI InChI=1S/C20H26N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3/t10-,11-,14+,15+,16?,17+,18-,19+,20-/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 (+)-Isoajmaline

The root of Rauvolfia serpentina

Protocol of (+)-Isoajmaline

Structure Identification
Helvetica Chimica Acta, 1981, 64(1):90-96.

Die absolute Konfiguration von Macrolin, einem Abbauprodukt des Alkaloides Villalstonin 179. Mitteilung über organische Naturstoffe.[Reference: WebLink]


METHODS AND RESULTS:
The absolute configuration of macroline (1), a degradration product of villalstonine (2), was determined. The chemical degradation of 1 gave a mixture of (–)‐(20S)‐20,21‐dihydro‐19‐desoxo‐macroline (9) and (–)‐(20R)‐20,21‐dihydro‐19‐desoxo‐macroline (10), which was related to the degradation products 9 of (+)‐ajmaline (3) and 10 of (+)-Isoajmaline(4) of known absolute configuration. Together with the complete relative stereochemistry of 2 the absolute configuration of 2 and of the second moiety of 2, (+)‐pleiocarpamine (20), could be derived.
CONCLUSIONS:
Since the absolute configuration of the (–)‐6, 7‐dihydroaspidospermidine moiety of (+)‐pycnanthinine has been known already [15], the structure by Gorman et al. [17] represents the absolute configuration of (+)‐pycnanthinine.

(+)-Isoajmaline Dilution Calculator

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(+)-Isoajmaline Molarity Calculator

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Preparing Stock Solutions of (+)-Isoajmaline

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0637 mL 15.3186 mL 30.6373 mL 61.2745 mL 76.5931 mL
5 mM 0.6127 mL 3.0637 mL 6.1275 mL 12.2549 mL 15.3186 mL
10 mM 0.3064 mL 1.5319 mL 3.0637 mL 6.1275 mL 7.6593 mL
50 mM 0.0613 mL 0.3064 mL 0.6127 mL 1.2255 mL 1.5319 mL
100 mM 0.0306 mL 0.1532 mL 0.3064 mL 0.6127 mL 0.7659 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 (+)-Isoajmaline

A New Ajmaline-type Alkaloid from the Roots of Rauvolfia serpentina.[Pubmed:30520580]

Nat Prod Commun. 2017 Apr;12(4):495-498.

A new ajmaline-type alkaloid, 21-Omicron-methylisoajmaline (1), together with twenty-one known compounds, a mixture of beta-sitosterol (2) and stigmasterol (3), reserpinine (4); tetrahydroalstonine (5), reserpine (6), venoterpine (7), yohimbine (8), 6'-O-(3,4,5-trimethoxybenzoyl)glomeratose A (9), (+)-Isoajmaline (10), 3-epi-alpha-yohimbine (11), methyl 3,4,5-trimethoxy-trans-cinnamate (12), a mixture of beta-sitosterol 3-Omicron-beta-D-glucopyranoside (13) and stigmasterol 3-Omicron-beta-D- glucopyranoside (14), rescidine (15), 7-deoxyloganic acid (16), ajmaline (17), suaveoline (18), (+)-tetraphyllicine (19), loganic acid (20), 3-hydroxysarpagine (21), and sarpagine (22), were isolated from the roots of Rauvolla serpentina. Their structures were elucidated by spectroscopic data analysis and comparison with literature data. Compounds 11, 12 and 15 were for the first time identified from the genus Rauvolfla and 5, 7, 11, 12, 15, 18 and 22 were found from R. sepentina for the first time. Compound 11 showed moderate anticholinesterase activity with IC(5)(0) value of 15.58 muM, whereas 6 exhibited strong vasorelaxant activity with the EC(5)(0) value of 0.05 muM.

A 1H- and 13C-NMR study of seven ajmaline-type alkaloids.[Pubmed:17252506]

Planta Med. 1996 Dec;62(6):577-9.

1H- and 13C-NMR spectral data are presented for ajmaline (1), 17-O-acetylajmaline (2), (+)-Isoajmaline (3), isosandwichine (4), rauflorine (5), vincamajine (6), and vincamedine (7). Some corrections to the previously reported assignments of compound 6 (1H-NMR) and compounds 3, 4 and 7 (13C-NMR) have been made. The 13C-NMR chemical shifts for rauflorine 5 are presented for the first time.

Monitoring of ajmaline in plasma with high-performance liquid chromatography.[Pubmed:1517305]

J Chromatogr. 1992 Mar 13;575(1):87-91.

A rapid, reliable and sensitive assay for routine determination of ajmaline in plasma by high-performance liquid chromatography with fluorimetric detection is presented. A low limit of detection in plasma (less than 1 ng/ml ajmaline) could be achieved by the extraction of plasma samples and the use of fluorimetric detection. Deproteinization of the plasma sample instead of extraction, or the use of an ultraviolet detector, yielded a higher limit of detection (less than 50 ng/ml). Two different eluents were studied. Eluent 1 allowed clear separation of ajmaline from (+)-Isoajmaline and sandwicine, but did not separate isoajamaline from sandwicine. With eluent 2, separation of (+)-Isoajmaline and sandwicine was achieved, but separation of ajmaline from sandwicine was less optimal than with eluent 1. Therefore, eluent 1 was used for further clinical studies. No interference was observed from therapeutic doses of other commonly co-administered drugs, such as acetylsalicylic acid, digoxin, digitoxin, ranitidine, dopamine, dobutamine, furosemide, captopril or glycerol trinitrate. In addition, the chemical stability of ajmaline and a possible rearrangement of ajmaline to its stereoisomers (+)-Isoajmaline and sandwicine was studied in vivo and in vitro. Ajmaline proved to be unusually stable under both in vivo and in vitro conditions.

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