| Identification | Back Directory | [Name]
palustrine | [CAS]
22324-44-3 | [Synonyms]
palustrine
(13S,16aS)-1,4,5,6,7,8,9,10,11,13,16,16a-Dodecahydro-13-[(S)-1-hydroxypropyl]pyrido[2,1-d][1,5,9]triazacyclotridecin-2(3H)-one | [Molecular Formula]
C17H31N3O2 | [MDL Number]
MFCD30834922 | [MOL File]
22324-44-3.mol |
| Hazard Information | Back Directory | [Description]
This alkaloid from Equisetum palustra was first obtained by Glet and his
colleagues and examined further by Karrer and Eugster. It is dextrorotatory with
[α]19D + 15.8° (CHC13) and forms crystalline salts, e.g. the dihydrochloride
hydrate, m.p. 188-190°C (dec.); [α]18D + 8.4° (H20) which yields an acid solu_x0002_tion in H20; diperchlorate, m.p. 270 C (dec.); dipicrate, m.p. lS0-lS0.SoC;
platinichloride as orange crystals, m.p. 221-3°C (dec.); dipicrolonate, m.p.
154°C and the reineckate, m.p. 174°C. The alkaloid contains two active hydrogens but no methoxyl groups and on reduction yields the dihydro derivative. The
latter base, on Hofmann degradation followed by hydrogenation and hydrolysis
yields dihydropalustramic acid, 6-(fj-hydroxypropyl)-piperid-2-yl-acetic acid.
From these observations, a modified structure for the alkaloid has been
suggested although the complete structure is not yet known with certainty. The
plant has sometimes given rise to cases of poisoning in cattle which appear to be
due to the alkaloid | [Definition]
ChEBI: Palustrine is a lactam and an azamacrocycle. | [References]
Glet, Gutschmidt, Glet., Zeit. Physiol. Chem., 244, 229 (1936)
Karrer, Eugster., Helv. Chim. Acta., 31, 1062 (1948)
Eugster.,Griot, Karrer., ibid, 36, 1387 (1953)
Structure:
Mayer et al., Helv. Chim. Acta, 51,661 (1968) |
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