(5aR,6S,8S,10S,11S,11aS,12aR,13R)-5-methyl-5a,6,8,9,10,11,11a,12-octahydro-5H-6,10:11,12a-dimethanoindolo[3,2-b]quinolizine-8,13-diol

Base Information

• Chemical Name: (5aR,6S,8S,10S,11S,11aS,12aR,13R)-5-methyl-5a,6,8,9,10,11,11a,12-octahydro-5H-6,10:11,12a-dimethanoindolo[3,2-b]quinolizine-8,13-diol
• CAS No.: 4360-12-7
• Molecular Formula: C20H26N2O2
• Molecular Weight: 326.48
• Wikidata: Q385858
• Metabolomics Workbench ID: 43555
• ChEMBL ID: CHEMBL2357792
• Mol file: 4360-12-7.mol

Synonyms:CHEBI:28462;(5aR,6S,8S,10S,11S,11aS,12aR,13R)-5-methyl-5a,6,8,9,10,11,11a,12-octahydro-5H-6,10:11,12a-dimethanoindolo[3,2-b]quinolizine-8,13-diol;DTXSID6045537;NCGC00016987-01;Ajimalin (TN);Ajmaline (JP17);SCHEMBL18950;ajmalan-17alpha,21alpha-diol;CHEMBL2357792;DTXCID4025537;HY-B1167;Tox21_110728;4-FORMYLPHENYL4-FORMYLBENZOATE;AKOS037515833;CS-4769;DB01426;CAS-4360-12-7;D00199;EN300-26869018;Q385858;(1R,9R,10S,12R,13S,14R,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2(7),3,5-triene-14,18-diol;(1R,9R,10S,12R,13S,14R,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-triene-14,18-diol

Chemical Property of (5aR,6S,8S,10S,11S,11aS,12aR,13R)-5-methyl-5a,6,8,9,10,11,11a,12-octahydro-5H-6,10:11,12a-dimethanoindolo[3,2-b]quinolizine-8,13-diol

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 189 °C
• Refractive Index: 1.701
• Boiling Point: 519.406 °C at 760 mmHg
• PKA: pKa 8.2 (Uncertain)
• Flash Point: 285.155 °C
• PSA: 46.94000
• Density: 1.373 g/cm³
• LogP: 1.55740
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• Water Solubility.: 489.7mg/L(30 oC)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 326.199428076
• Heavy Atom Count: 24
• Complexity: 570

Purity/Quality:

99%, ^*data from raw suppliers

Ajmaline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 25-20/21/22
• Safety Statements: 13-45-36

MSDS Files:

Useful:

• Canonical SMILES: CCC1C2CC3C4C5(CC(C2C5O)N3C1O)C6=CC=CC=C6N4C
• Isomeric SMILES: CC[C@H]1[C@@H]2C[C@H]3[C@H]4[C@@]5(C[C@@H](C2[C@H]5O)N3[C@@H]1O)C6=CC=CC=C6N4C
• Description: Rauwolfia (Luo Fu Mu) is derived from the plants Rauvolfia verticillata (Lour.) Baill. and R. yunnanensis Tsiang, and the root is usually used as its medicinal part. R. verticillata (Lour.) Baill. var. hainanensis Tsiang and R. vomitoria Afzel. ex Spreng have been also used as traditional Chinese herb. Rauwolfia is one of the important traditional herbs in southern China. Its scope of treatment includes cold, fever, sore throat, headache, and dizziness caused by hypertension, abdominal pain and diarrhea, scabies, and so on. Rauwolfia is also used to treat insomniac dizziness, bruises, sprains, and venomous snake bites in folk. In the “Flora of China,” 135 species of Rauwolfia were recorded, mostly distributed in the tropics and subtropics, a few in the temperate regions. There are nine species, four varieties, and three cultivated species in China.
• Physical properties: Appearance: white or yellowish crystal powder. Melting point: its anhydride is 205– 207?°C. Optical rotation: +144° (chloroform). Solubility: well soluble in organic solvents, such as methanol, ethanol, etc., and slightly soluble in water. Storage temperature: 2–8?°C.
• Uses: An antiarrhythmic agent isolated from Rauwolfia serpentina. For use as an antiarrhythmic agent.
• Therapeutic Function: Antiarrhythmic
• Clinical Use: Ajmaline has the anti-arrhythmic effects for the treatment of atrial or ventricular extrasystoles, paroxysmal supraventricular or ventricular tachycardia, and paroxysmal atrial fibrillation. The lethal dose for human ranged from 100 to 500?mg/kg.

Technology Process of (5aR,6S,8S,10S,11S,11aS,12aR,13R)-5-methyl-5a,6,8,9,10,11,11a,12-octahydro-5H-6,10:11,12a-dimethanoindolo[3,2-b]quinolizine-8,13-diol

There total 1 articles about (5aR,6S,8S,10S,11S,11aS,12aR,13R)-5-methyl-5a,6,8,9,10,11,11a,12-octahydro-5H-6,10:11,12a-dimethanoindolo[3,2-b]quinolizine-8,13-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1R,4aS,7S,7aR)-nepetalactone (69252-84-2) → ajmaline (509-37-5,4360-12-7,6835-90-1,6989-79-3,22395-56-8,32999-94-3,51019-46-6,73089-81-3,149496-13-9) + vomilenine (6880-50-8,107585-43-3,134356-24-4)

Guidance literature:

for 240h;

DOI:10.1016/S0040-4039(00)84672-9

Reference yield: 87.0%

ajmaline (509-37-5,4360-12-7,6835-90-1,6989-79-3,22395-56-8,32999-94-3,51019-46-6,73089-81-3,149496-13-9) + benzyl chloroformate (501-53-1,94274-21-2) → Carbonic acid benzyl ester (3S,4R,8S,13aR)-3-ethyl-8-hydroxy-13-methyl-1,3,4,7,8,13,13a,13b-octahydro-2H,6H-2,7-cyclo-6,8a-methano-pyrido[1',2':1,2]azepino[3,4-b]indol-4-yl ester (133761-67-8)

Guidance literature:

With sodium hydroxide; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1016/S0040-4020(01)86414-0

Reference yield:

ajmaline (509-37-5,4360-12-7,6835-90-1,6989-79-3,22395-56-8,32999-94-3,51019-46-6,73089-81-3,149496-13-9) → Nβ-propyl-ajmaline bitartrate (2589-47-1,35718-28-6,64970-45-2,99269-88-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2.4 g / acetonitrile / 7 h / Heating

2.1: NaHCO₃ / H₂O; ethyl acetate / 6 h

2.2: 1.5 g / acetone / 0 °C

With sodium hydrogencarbonate; In water; ethyl acetate; acetonitrile; 1.1: Alkylation / 2.1: anion exchange / 2.2: anion exchange;

upstream raw materials:

(1R,4aS,7S,7aR)-nepetalactone

Downstream raw materials:

diacetylajmaline

(17R)-17,21α-dihydroxy-4-methyl-ajmalanium; iodide

17,21-diacetylisosandwicine

(17R)-17,21β-dihydroxy-4-methyl-20βH-ajmalanium; iodide

Refernces