| Identification | Back Directory | [Name]
(-)-Pancracine | [CAS]
21416-14-8 | [Synonyms]
Pancracine
(-)-Pancracine
(6aS)-5,6a,7,8,9,11-Hexahydro-6β,11β-methano-6H-1,3-benzodioxolo[5,6-c][1]benzazepine-8α,9β-diol
6,11-Methano-6H-1,3-benzodioxolo[5,6-c][1]benzazepine-8,9-diol, 5,6a,7,8,9,11-hexahydro-, (6R,6aS,8S,9S,11S)- | [Molecular Formula]
C16H17NO4 | [MOL File]
21416-14-8.mol | [Molecular Weight]
287.31 |
| Hazard Information | Back Directory | [Description]
This alkaloid occurs in Narcissus poeticus, Pancratium maritium and Rhodo_x0002_phiala bifida. It yields long, colourless prisms when recrystallized from MeOH
and is laevorotatory with [α]25D - 74° (c 0.02, MeOH). The ultraviolet spectrum
has two absorption maxima at 241 and 292 mil. It yields a crystalline perchlorate, m.p. 163-6°C and a picrate, m.p. 249-2S2°C. Two non-phenolic
hydroxyl groups and one methylenedioxy group are present in the molecule.
The 2-a-O-acetate is an amorphous solid which cannot be obtained crystalline
but the 3-{3-0-acetate forms colourless crystals from MeOH, m.p. 213-6°C. The
O,O-diacetate, also crystalline, has m.p. 163-S°C. The O-methyl derivatives
occur naturally, the 2-methyl compound is Montanine (q.v.) and the 2:3-dimethyl
ether is Manthine (q.v.). The structure is based primarily upon the mass spectrum
fragmentation pattern. | [Definition]
ChEBI: Hippagine is a benzazepine. | [References]
Sandberg, Michel., Lloydia, 26, 78 (1963)
Structure:
Wildman, Brown.,J. Amer. Chem. Soc., 90,6439 (1968) |
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