Vomicine

Base Information

• Chemical Name: Vomicine
• CAS No.: 125-15-5
• Deprecated CAS: 1393-36-8,28596-09-0
• Molecular Formula: C₂₂H₂₄N₂O₄
• Molecular Weight: 380.444
• UNII: 4R9445MB8M
• DSSTox Substance ID: DTXSID30154540
• Wikidata: Q27108554
• ChEMBL ID: CHEMBL2164625
• Mol file: 125-15-5.mol

Synonyms:Vomicine;125-15-5;Strychnicine;Vomicin;UNII-4R9445MB8M;CHEBI:10019;4R9445MB8M;(1S,10S,22R,23R,24S)-15-hydroxy-4-methyl-9-oxa-4,13-diazahexacyclo[11.6.5.01,24.06,22.010,23.014,19]tetracosa-6,14(19),15,17-tetraene-12,20-dione;4-Hydroxy-19-methyl-16,19-secostrychnidine-10,16-dione;12H-6A,4-(ETHANIMINOMETHANO)INDOLO(3,2,1-IJ)OXEPINO(2,3,4-DE)QUINOLINE-6,12(2H)-DIONE, 4A,5,13,13A,13B,13C-HEXAHYDRO-10-HYDROXY-16-METHYL-, (4AR,6AS,13AS,13BR,13CS)-;12H-6a,4-(Ethaniminomethano)indolo[3,2,1-ij]oxepino[2,3,4-de]quinoline-6,12(2H)-dione, 4a,5,13,13a,13b,13c-hexahydro-10-hydroxy-16-methyl-, (4aR,6aS,13aS,13bR,13cS)-;VOMICINE [MI];16,19-Secostrychnidine-10,16-dione, 4-hydroxy-19-methyl-;SCHEMBL3371643;CHEMBL2164625;DTXSID30154540;19764-19-3;HY-N2616;AKOS032949106;AC-34199;MS-26224;CS-0023019;C09255;Q27108554;(4AR,6AS,13AS,13BR,13CS)-4A,5,13,13A,13B,13C-HEXAHYDRO-10-HYDROXY-16-METHYL-12H-6A,4-(ETHANIMINOMETHANO)INDOLO(3,2,1-IJ)OXEPINO(2,3,4-DE)QUINOLINE-6,12(2H)-DIONE;12H-6a,4-(Ethaniminomethano)indolo(3,2,1-i)oxepino(2,3,4-de)quinoline-6,12(2H)-dione, 4a,5,13,13a,13b,13c-hedahydro-10-hydroxy-16-methyl-, (4aR,6aS,13aS,13bR,13cS)-;2H-6a,4-(Ethaniminomethano)indolo(3,2,1-i)oxepino(2,3,4-de)quinoline-6,12(2H)-dione, 4a,5,13,13a,13b,13c-hedahydro-10-hydroxy-16-methyl-, (4aR-(4aR*,6aS*,13aS*,13bR*,13cS*))-

Chemical Property of Vomicine

Chemical Property:

• Vapor Pressure: 8.11E-17mmHg at 25°C
• Melting Point: 286-290℃ (dec.)
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 636.9°Cat760mmHg
• Flash Point: 339°C
• PSA: 70.08000
• Density: 1.44g/cm³
• LogP: 1.61770
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 380.17360725
• Heavy Atom Count: 28
• Complexity: 766

Purity/Quality:

≥98% ^*data from raw suppliers

Vomicine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23C4C5C(CC2=O)C(=CCOC5CC(=O)N4C6=C3C=CC=C6O)C1
• Isomeric SMILES: CN1CC[C@]23[C@@H]4[C@H]5[C@@H](CC2=O)C(=CCO[C@H]5CC(=O)N4C6=C3C=CC=C6O)C1
• Description: Schaefer has obtained this base from old seeds of Strychnos Nux-vomica which had deteriorated where is occurs to the extent of about 0.1 per cent. It forms colourless crystals from EtOH which become yellow on exposure to light. With H2S04 it gives a colourless solution that becomes green on the addition of potassium dichromate. From the available evidence it seems likely that it is not a true alkaloid but a decomposition product of either strychnine or brucine.
• Uses: Vomicine is an antiplasmoidal alkaloid extracted from the stem bark of Strychnos malacoclados and is useful against malaria.

Technology Process of Vomicine

There total 13 articles about Vomicine 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:

2-Brom-16-hydroxy-19-methyl-4-nitrostrychnin → strychnicine (125-15-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / sodium-amalgan / methanol; H₂O / 22 h / Ambient temperature

2: 1) 5percent sodium nitrite, 2) 2N H₂SO₄ / 1) 2N H₂SO₄, 50 deg C, 5 min, 2) 1 h, reflux

With sodium amalgam; sulfuric acid; sodium nitrite; In methanol; water;

DOI:10.1002/jlac.198019800610

Reference yield:

2-Brom-16-hydroxy-19-methylstrychnin (757892-64-1) → strychnicine (125-15-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / 2N HNO₃ / H₂O / pH = 2-3

2: 77 percent / sodium-amalgan / methanol; H₂O / 22 h / Ambient temperature

3: 1) 5percent sodium nitrite, 2) 2N H₂SO₄ / 1) 2N H₂SO₄, 50 deg C, 5 min, 2) 1 h, reflux

With sodium amalgam; sulfuric acid; nitric acid; sodium nitrite; In methanol; water;

DOI:10.1002/jlac.198019800610

Reference yield:

(-)-pseudostrychnine (465-62-3) → strychnicine (125-15-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / 6 h / Heating

2: 94 percent / Br₂ / H₂O; HBr / 1 h / 80 °C

3: 88 percent / 2N HNO₃ / H₂O / pH = 2-3

4: 77 percent / sodium-amalgan / methanol; H₂O / 22 h / Ambient temperature

5: 1) 5percent sodium nitrite, 2) 2N H₂SO₄ / 1) 2N H₂SO₄, 50 deg C, 5 min, 2) 1 h, reflux

With sodium amalgam; sulfuric acid; bromine; nitric acid; sodium nitrite; In methanol; water; hydrogen bromide;

DOI:10.1002/jlac.198019800610

upstream raw materials:

4-Amino-16-hydroxy-19-methylstrychnin

3,12-dihydroxystrychnine

methyl iodide

hydrogenchloride

Downstream raw materials:

11-((Ξ)-benzylidene)-4-hydroxy-19-methyl-16,19-seco-strychnidine-10,16-dione

Refernces

• 1、 Rosenmund,Schmitt,Franke. "Vomicine from strychnine". . p. 895 - 907. Retrieved 2007/10/02.