(-)-Voacangine

Base Information

• Chemical Name: (-)-Voacangine
• CAS No.: 510-22-5
• Molecular Formula: C22H28 N2 O3
• Molecular Weight: 368.476
• European Community (EC) Number: 687-877-9
• UNII: 9SY76D3YUK
• Nikkaji Number: J14.004J
• Wikipedia: Voacangine
• Wikidata: Q105167451
• ChEMBL ID: CHEMBL4575134
• Mol file: 510-22-5.mol

Synonyms:voacangine

Chemical Property of (-)-Voacangine

Chemical Property:

• Vapor Pressure: 7.52E-11mmHg at 25°C
• Melting Point: 223-224℃ (dec.)
• Boiling Point: 518.4°Cat760mmHg
• Flash Point: 267.3°C
• PSA: 54.56000
• Density: 1.25g/cm³
• LogP: 3.20170
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 368.20999276
• Heavy Atom Count: 27
• Complexity: 598

Purity/Quality:

98%,99%, ^*data from raw suppliers

(-)-Voacangine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CC2CC3(C1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC
• Isomeric SMILES: CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC
• Description: This alkaloid is of widespread occurrence, being found in Stemmadenia species and also is Vocanga africana, v. dregii and V. obtusa. It forms colourless needles when crystallized from MeOH and has [0'10 - 42° (c 1.0, CHCI3). It sublimes under vacuum at 135°CjO.01 mm and is readily soluble in CHC13 or Me2CO, but only sparingly so in EtOH or MeOH. Hydrolysis with KOH followed by acidification with HCl yields Ibogaine (q.v.).
• Uses: (-)-Voacangine is a bisindole alkaloid with ether-?a-?go-?go-?related gene channel blocker activity in vitro. hERG channel blocker.

Technology Process of (-)-Voacangine

There total 6 articles about (-)-Voacangine 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:

(–)-10-OH-coronaridine → 12-methoxyibogamine-18-carboxylic acid methylester (510-22-5)

Guidance literature:

With NADPH; In aq. buffer; at 37 ℃; for 2h; pH=9; Enzymatic reaction;

DOI:10.1021/jacs.9b05999

Reference yield:

stemmadenine acetate → 12-methoxyibogamine-18-carboxylic acid methylester (510-22-5)

Guidance literature:

Multi-step reaction with 5 steps

1: T_. iboga precondylocarpine acetate synthase 1; FAD / aq. buffer / 2 h / 37 °C / pH 9.5 / Enzymatic reaction

2: NADPH / aq. buffer / 1 h / 37 °C / pH 9.5 / Enzymatic reaction

3: NADPH / aq. buffer / pH 9.5 / Enzymatic reaction

4: NADPH / aq. buffer / 24 h / 30 °C / pH 7.5 / Enzymatic reaction

5: NADPH / aq. buffer / 2 h / 37 °C / pH 9 / Enzymatic reaction

With NADPH; In aq. buffer;

DOI:10.1021/jacs.9b05999

Reference yield:

C23H27N2O4(1+) → 12-methoxyibogamine-18-carboxylic acid methylester (510-22-5)

Guidance literature:

Multi-step reaction with 4 steps

1: NADPH / aq. buffer / 1 h / 37 °C / pH 9.5 / Enzymatic reaction

2: NADPH / aq. buffer / pH 9.5 / Enzymatic reaction

3: NADPH / aq. buffer / 24 h / 30 °C / pH 7.5 / Enzymatic reaction

4: NADPH / aq. buffer / 2 h / 37 °C / pH 9 / Enzymatic reaction

With NADPH; In aq. buffer;

DOI:10.1021/jacs.9b05999

Downstream raw materials:

12-hydroxyibogamine

ibogaine

C₂₈H₃₂N₂O₃

ibogaine hydrochloride

Refernces

• 1、 Puisieux,Devissaguet,Miet,Poisson. "Alkaloids of Voacanga. V. N-oxy-voacamine". . p. 251 - 253. Retrieved 2007/10/07.