(5alpha)-6,7,8,14-tetradehydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol

Description

This alkaloid was first obtained from the leaves of Papaver orientalis by moistening the dried leaves with ammonia and extracting them with CH2CI2. Subsequently it has been isolated from P. bracteaturn and on recrystallization from EtOH it forms colourless needles. It is readily soluble in CHCI3, sparingly so in EtOH and Me2CO and insoluble in H20. It is laevorotatory with [α]_D - 211.8° (CHC13) and yields a hydrochloride, m.p. 258-9°C (dec.) and a methiodide, m.p. 207-8°C. The alkaloid dissolves in aqueous NaOH yielding a crystalline sodium derivative.

Chemical Properties

Light Tan Solid

Uses

The major metabolite of Thebaine. Oripavine possesses an analgesic potency comparable to Morphine; it is not clinically useful due to severe toxicity and low therapeutic index. An opiate.

Definition

ChEBI: Oripavine is a morphinane alkaloid.

References

Yunusov, Konovalova, Orekhov., Ber., 68,2158 (1935) ^{Yunusov, Konovalova, Orekhov.,J. Gen. Chern. USSR, 10,641 (1940)
Kiselev, Konovalova., ibid, 18,142 (1948)}