Veratramine

Base Information

• Chemical Name: Veratramine
• CAS No.: 60-70-8
• Molecular Formula: C₂₇H₃₉NO₂
• Molecular Weight: 409.612
• European Community (EC) Number: 683-091-5
• NSC Number: 17821,23880
• UNII: RK363YG315
• DSSTox Substance ID: DTXSID40871534
• Nikkaji Number: J4.805D
• Wikipedia: Veratramine
• Wikidata: Q15427945
• Metabolomics Workbench ID: 53511
• ChEMBL ID: CHEMBL464724
• Mol file: 60-70-8.mol

Synonyms:5-methyl-2-(1-(2,3,4,6,6a,11,11a,11b-octahydro- 3-hydroxy-10,11b-dimethyl-1H-benzo(a)fluoren-9- yl)ethyl)piperidin-3-ol;veratramin;veratramine

Chemical Property of Veratramine

Chemical Property:

• Vapor Pressure: 1.33E-13mmHg at 25°C
• Melting Point: 122-1240C
• Refractive Index: 1.6400 (estimate)
• Boiling Point: 565°C at 760 mmHg
• PKA: 14.82±0.60(Predicted)
• Flash Point: 86.2°C
• PSA: 52.49000
• Density: 1.14g/cm³
• LogP: 4.92330
• Storage Temp.: -20?C Freezer
• Solubility.: Soluble in DMSO (up to 12 mg/ml) or in Ethanol (up to 10 mg/ml)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 409.298079487
• Heavy Atom Count: 30
• Complexity: 676

Purity/Quality:

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

Veratramine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CC1CC(C(NC1)C(C)C2=C(C3=C(C=C2)C4CC=C5CC(CCC5(C4C3)C)O)C)O
• Isomeric SMILES: C[C@H]1C[C@H]([C@@H](NC1)[C@@H](C)C2=C(C3=C(C=C2)[C@@H]4CC=C5C[C@H](CC[C@@]5([C@H]4C3)C)O)C)O
• Description: This alkaloid occurs naturally in Veratrum grandi/lorum and V. viride and is also formed during the hydrolysis of Veratrosine (q.v.). It forms colourless crystals of the monohydrate from aqueous EtOH and has [α]19D - 70° (MeOH). The hydrochloride forms colourless plates from EtOH, m.p. 20l-2°C and the picrate, yellow plates, m.p. 217.5 - 218°C. Two non-phenolic hydroxyl groups and an imino group are present and the triacetyl derivative, m.p. 205.5-206°C; [α]14.5D + 37.8° (MeOH), on controlled hydrolysis furnishes the N-acetyl com_x0002_pound, m.p. 176-8°C. The O-acetate has also been prepared as colourless prisms from aqueous EtOH, m.p. 20l-2°C but it is still uncertain which of the hydroxyl groups is acetylated in this derivative. Treatment with methyl iodide in MeOH in the presence of sodium carbonate gives N-methylveratraminc methiodide, m.p. 268°C (dec.) from which the methochloride, m.p. 277°C can be obtained. On catalytic hydrogenation, the base furnishes the dihydro derivative, m.p. 198- 200°C; [α]27D + 27.4°, which forms the N-acetyl compound, m.p. 220-3°C; [α]28D + 81° and the triacetyl derivative, m.p. l89.5-190.5°C; [α]24D + 84°.
• Uses: It is useful as signal transduction inhibitor for treating tumors The hedgehog (Hh) signaling pathway, which is blocked by cyclopamine , plays a key role in morphogenesis and has potential applications in the treatment of cancer. Veratramine, a teratogenic steroidal alkaloid isolated from the corn lily (Veratrum sp.), is an analog of cyclopamine that can inhibit the Hh signaling-dependent proliferation of NIH/3T3 cells at 8 μM. Additionally, veratramine has anti-thrombotic activity as it dose dependently inhibits platelet aggregation in rabbits ex vivo. While it may be most useful as a signal transduction inhibitor for treating tumors, veratramine also induces serotonin release and inhibits its re-uptake in the CNS.

Technology Process of Veratramine

There total 3 articles about Veratramine 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:

→ veratramine (60-70-8)

Guidance literature:

DOI:10.1021/ja00993a049 DOI:10.1016/S0040-4020(01)92644-4

Reference yield:

→ Veratramin (60-70-8,34022-65-6,34022-66-7)

Guidance literature:

Cyclopamin, HCl;

DOI:10.1016/S0031-9422(00)85817-3

Reference yield:

→ Veratramin (60-70-8,34022-65-6,34022-66-7)

Guidance literature:

Ic, KOH/Hydrazinhydrat;

DOI:10.1016/S0040-4020(01)97749-X

Refernces

• 1、 -. "Isolation of Cyclopamine". Paragraph 0115; 0117. . Retrieved 2016/07/05.