loline
loline Basic information
- Product Name:
- loline
- Synonyms:
-
- loline
- (2R,3aβ,6aβ)-Hexahydro-N-methyl-2α,4α-methano-4H-furo[3,2-b]pyrrol-3α-amine
- Festucine
- 2,4-Methano-4H-furo[3,2-b]pyrrol-3-amine, hexahydro-N-methyl-, (2R,3R,3aS,4S,6aS)-
- CAS:
- 25161-91-5
- MF:
- C8H14N2O
- MW:
- 154.212
- Mol File:
- 25161-91-5.mol
loline Chemical Properties
- Boiling point:
- 103 °C(Press: 5 Torr)
- Density
- 1.20±0.1 g/cm3(Predicted)
- pka
- 9.36±0.20(Predicted)
loline Usage And Synthesis
Description
This oily alkaloid has been obtained from a species of grass, Lotium cuneatum Nevski. It has a density of D 20 1.1343 and a refractive index of n20D 1.5505. It behaves as a diacidic base yielding a series of well crystalline salts and derivatives, e.g. the dihydrochloride, m.p. 256-7°C; [α]15D + 6.2° (H20); dihydrobromide, m.p. 254-5°C (dec.); [α]20D + 3.5° (c 4.29, H20); dihydriodide, m.p. 233-5°C (dec.); [α]34D + 5.0° (c 13.2 H20); perchlorate, m.p. 282°C with almost explosive decomposition; sulphate, yellow needles, m.p. 250-2°C (dec.); mononitrate,m.p. 208-2l0°C; dinitrate, m.p. l48-9°C; [α]38D + 6.18° (c 6.94, H20); dipicrate, m.p. 258-260°C (dec.); methiodide, m.p. 2l0-loC and the N-nitroso derivative, m.p. 64°C. The N-acetyl derivative yields a crystalline hydrochloride, m.p. 197-8°C; [α]20D + 36.9° (H20) and the N-methyl compound is obtained as a colourless oil, b.p. 90-l oC/2 mm; [α]31D+ 9.31° (c 9.5, MeOH). The alkaloid possesses an ether oxygen bridging the pyrrolizidine moiety.
Definition
ChEBI: Loline is a loline alkaloid with formula C8H14N2O. It is a secondary amino compound and a loline alkaloid.
Hazard
A poison.
References
Yunusov, Akramov., J. Gen. Chern., USSR, 25, 1765 (1955)
Yunusov, Akramov., ibid, 30,699,705,3105 (1960)
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