CID 20055020

Base Information

• Chemical Name: CID 20055020
• CAS No.: 482-68-8
• Molecular Formula: C19H22 N2 O2
• Molecular Weight: 310.396
• European Community (EC) Number: 207-583-2
• Metabolomics Workbench ID: 53422
• Mol file: 482-68-8.mol

Synonyms:sarpagine

Chemical Property of CID 20055020

Chemical Property:

• Melting Point: 320°C
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 524.6°Cat760mmHg
• PKA: 10.24±0.40(Predicted)
• Flash Point: 271.1°C
• PSA: 59.49000
• Density: 1.39g/cm³
• LogP: 2.66750
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 310.168127949
• Heavy Atom Count: 23
• Complexity: 522

Purity/Quality:

Sarpagine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1CN2C3CC1C(C2CC4=C3NC5=C4C=C(C=C5)O)CO
• Isomeric SMILES: C/C=C\1/CN2[C@H]3C[C@@H]1C([C@@H]2CC4=C3NC5=C4C=C(C=C5)O)CO
• Description: This base has been isolated from Rauwolfia serpentina and is an isomer of Ajmalinine (q.v.). Pharmacologically it has between three and four times the effect of the total Rauwolfia alkaloids on isolated rabbit uterus and is very specific. In the cat, the blood pres~ure is lowered by 0.5-2.0 mgm per kilo body weight. The toxicity is low.

Technology Process of CID 20055020

There total 31 articles about CID 20055020 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: 86.0%

10-deoxysarpagine (604-99-9,1358-75-4,119241-70-2,119241-73-5,124096-81-7,126640-98-0) → Sarpagine (482-68-8,102490-01-7)

Guidance literature:

DOI:10.1016/S0040-4020(01)91118-4

Reference yield: 80.0%

10-methoxynormacusine B (522-47-4) → sarpagine (482-68-8)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1002/anie.201206015

Reference yield: 80.0%

P(S)-lochnerine dimer → sarpagine (482-68-8)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/anie.201206015

upstream raw materials:

(+)-3-ethylidene-1,3,4,7,12,12b-hexahydro-13-hydroxymethyl-2H,6H-2,6-methanoindolo[2,3-a]quinolizine

(6S,11aS,E)-9-ethylidene-2-methoxy-6,8,9,10,11a,12-hexahydro-6,10-methanoindolo-[3,2-b]quinolizin-11(5H)-one

(+)-10-methoxyvellosimine

10-methoxynormacusine B

Refernces

Macroline, akuammiline, sarpagine, and ajmaline alkaloids from Alstonia macrophylla

10.1016/j.phytochem.2013.11.014

Siew-Huah Lim et al. detail the isolation and structural determination of 17 new indole alkaloids from the stem-bark and leaf extracts of the Malayan Alstonia macrophylla. These alkaloids, which include macroline, sarpagine, akuammiline, and ajmaline types, were identified using NMR, MS, and X-ray diffraction analysis. Six of these alkaloids demonstrated the ability to reverse multidrug resistance (MDR) in vincristine-resistant KB cells. The study highlights the chemical diversity of Alstonia macrophylla and its potential for yielding compounds with significant biological activities, particularly in the context of overcoming drug resistance in cancer therapy.