Description
An alkaloid found in Duboisia myoporoides, the base crystallizes from EtOH in
colourless, nacreous plates and has [α]20D - 9.0° (c 5.0, EtOH), or - 4.0° (c 5.0,
H2O). It yields a crystalline hydrobromide as colourless needles, m.p. l70-2°C;
[α]20D + 5.0° (c 20.0, H20); picrate, m.p. lS2-3°C; methiodide, m.p. 20S.SoC
and the acetyl derivative, characterized as the hydrobromide, m.p. 197°C. The
isovaleryl ester forms a hydrochloride, m.p. l24-SoC; [α]D + 2.6° (c 3.78,
EtOH) and a hydrobromide, m.p. l76-7°C. Treatment of the hydrobromide
with thionyl chloride gives norvaleroidine due to demethylation, a colourless
syrup which furnishes a crystalline hydrobromide, m.p. 270°C; [α]20D + 1 °
(c 20.0, H20). On hydrolysis with aqueous Ba(OHh, the base gives dihydroxytropane and isovaleric acid while oxidation with KMn04 furnishes norvalieroidine
and a base C13H190 4N, m.p. 136°C; [α]20D - 16.6° (c 7.4, EtOH).
References
Barger, Martin, Mitchell.,!. Chem. Soc., 1820 (1937)
Barger, Martin, Mitchell., ibid, 1685 (1938)
Martin, Mitchell., ibid, 1155 (I 940)
Mitchell, Troutner., ibid, 1330 (I 947)
Fodor, Kovacs., ibid, 2341 (1953)
Fodor, Vincze, Toth., ibid, 1349 (1957)
Fodor, Vincze, Toth., ibid, 3219 (1961)
