METELOIDINE
- CAS No.
- 526-13-6
- Chemical Name:
- METELOIDINE
- Synonyms
- Meteloidin;METELOIDINE;Meteloidin-14C;6,7-Dihydroxy-3-tiglyloxytropane;3-tigloyloxy-6,7-dihydroxytropane;3endo-tigloyloxy-tropane-6exo,7exo-diol;(E)-2-Methyl-2-butenoic acid (1S,5R)-6β,7β-dihydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3α-yl ester;2-Butenoic acid, 2-methyl-, (1R,3-endo,5S,6S,7R)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (2E)-rel-
- CBNumber:
- CB71433080
- Molecular Formula:
- C13H21NO4
- Molecular Weight:
- 255.31
- MDL Number:
- MOL File:
- 526-13-6.mol
| Melting point | 141-142° |
|---|---|
| Boiling point | 383.9±41.0 °C(Predicted) |
| Density | 1.23±0.1 g/cm3(Predicted) |
| pka | 13.48±0.60(Predicted) |
| FDA UNII | JN0S84O367 |
METELOIDINE Chemical Properties,Uses,Production
Description
A tropane alkaloid first found by Pyman and Reynolds in Datura rneteloides, the base also occurs in D. ferox and the leaves of Erythroxylurn australe. It crystallizes from C6H6 in tabular needles and is readily soluble in CHC13 or EtOH but only slightly so in Et20, C6H6 or H20. The hydrochloride is obtained as chiselshaped needles of the diliydrate, m.p. 250°C (dry); the aurich10ride hemihydrate also forms needles, m.p. 149-1500 C, the picrate, m.p. 177-1800 C and the reineckate, m.p. 140°C (dec.). Hydrolysis with Ba(OHh furnishes tiglic acid and teloidine, CSH1S0 3N, m.p. 168-9°C. The latter may be characterized as the crystalline hydrochloride, m.p. > 300°C; hydrobromide, m.p. 295°C and the aurichloride, m.p. 225°C. The alkaloid is physiologically inactive.
References
Pyman, Reynolds.,]. prakt. Chern., 64,274 (1901)
Evans, Partridge., Chern. Abstr., 42,7486 (1948)
Sheehan, Bissell.,]. Org. Chern., 19,270 (1954)
Heusner., Z. Naturforsch., 96,683 (1954)
Heusner., Ber., 87, 1032 (1954)
Johns, Lamberton., Austral. J. Chern., 20,1301 (1967)