| Identification | Back Directory | [Name]
veratramine | [CAS]
60-70-8 | [Synonyms]
NSC 2388
NSC 23880
NSC 17821
veratraMin
AIDS011940
veratramine
Vreaframine
14,15,16,17-Tetradehydroveratraman-3β,23β-diol
(3,23)-14,15,16,17-Teradehydroveratraman-3,23-diol
(3b,23b)-14,15,16,17-Teradehydroveratraman-3,23-diol
5S-methyl-2S-[1S-[2,3S,4,6,6aR,11,11aS,11bR-octahydro-3R-hydroxy-10,11b-dimethyl-1H-benzo[a]fluoren-9-yl]ethyl]-3-piperidinol
(2S,3R,5S)-5-Methyl-2-[(1S)-1-[(3S,6aR,11aS,11bR)-2,3,4,6,6a,11,11a,11b-octahydro-3-hydroxy-10,11b-dimethyl-1H-benzo[a]fluoren-9-yl]ethyl]-3-piperidinol | [Molecular Formula]
C27H39NO2 | [MDL Number]
MFCD00468124 | [MOL File]
60-70-8.mol | [Molecular Weight]
409.61 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
122-1240C | [alpha ]
D25 -71.8° (c = 1.21); D25 -70° (c = 1.56 in methanol) | [Boiling point ]
529.83°C (rough estimate) | [density ]
1.0393 (rough estimate) | [refractive index ]
1.6400 (estimate) | [storage temp. ]
-20?C Freezer | [solubility ]
Soluble in DMSO (up to 12 mg/ml) or in Ethanol (up to 10 mg/ml) | [form ]
solid | [pka]
14.82±0.60(Predicted) | [color ]
Tan | [λmax]
268nm(lit.) | [Merck ]
14,9952 | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. | [CAS DataBase Reference]
60-70-8 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
It is useful as signal transduction inhibitor for treating tumors | [Definition]
ChEBI: A piperidine alkaloid comprising the 14,15,16,17-tetradehydro derivative of veratraman having two hydroxy groups at the 3- and 23-positions. | [Uses]
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. | [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°. | [References]
Saito., Bull. Chem. Soc., Japan, 15, 22 (1940)
Jacobs, Craig.,J. Biol. Chem., 155,565 (1944)
Jacobs,.Craig., ibid, 160,555 (1945)
Tamm, Wintersteiner., J. Amer. Chem. Soc., 74,3842 (1952)
Mass spectra:
Budzikiwicz., Tetrahedron, 20,2267 (1964)
Synthesis:
Masamune, Takasugi, Murai., Tetrahedron, 27,3369 (1971) |
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