| Identification | Back Directory | [Name]
tigloidine | [CAS]
495-83-0 | [Synonyms]
Tiglyssin
Tigloidin
tigloidine
Tigloyltropine
Tigloyltropeine
3α-Tigloyloxytropane
2-Methylcrotonic acid (1R,5S)-tropan-3β-yl ester | [EINECS(EC#)]
207-810-5 | [Molecular Formula]
C13H21NO2 | [MDL Number]
MFCD00867194 | [MOL File]
495-83-0.mol | [Molecular Weight]
223.314 |
| Chemical Properties | Back Directory | [Boiling point ]
290.2±33.0 °C(Predicted) | [density ]
1.06±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Oil | [pka]
10.03±0.40(Predicted) | [color ]
Light yellow to yellow |
| Hazard Information | Back Directory | [Description]
A tropine alkaloid isolated from Duboisia rnyoporoides, this base is a colourless
syrup which yields crystalline salts. The hydrobromide forms colourless, tabular
crystals m.p. 234-5°C and is optically inactive; the aurichloride crystallizes as
yellow plates, m.p. 213.5- 2140 C; the picrate as yellow rectangular plates, m.p.
239°C and the methiodide as square plates, m.p. 244-5°C. The alkaloid is
unsaturated and the hydro bromide, on hydrogenation, furnishes dihydrotigloidine,
giving a picrate, m.p. l34-5°C. When treated with bromine in CHC13 it forms
dibromodihydrotigloidine, m.p. 187°C (dec.). The free base may be hydrolyzed
by boiling with H20 when it furnishes pseudotropine and tiglic acid. The base is
therefore the tiglyl ester of pseudotropine. By comparison, tiglyltropine gives a
hydrobromide with m.p. 207°C and a picrate, m.p. 200°C. | [Uses]
Tigloidin is an analogue of atropine, with anticholinergic activity. | [in vivo]
Tigloidine hydrobromide (20-60 mg/kg, i.p.) fails to protect the mice against the lethal effect of physostigmine, but at 100 mg/kg and above, it protects 80% of the animals against the lethal effect. Tigloidine markedly prevents tremor and salivation produced by tremorine at 80-100 mg/kg, but fails to prevent these effects in doses up to 40 mg/kg. Tigloidine (up to 100 mg/kg, i.p) does not significantly affects reserpine and tetrabenazine induced sedation and ptosis in mice. Tigloidine (25-50 mg/kg, i.p.) also fails to cause any behavioral changes in the cats[1]. | [storage]
Store at -20°C | [References]
Barger, Martin, Mitchel1.,J. Chern. Soc., 1820 (1937) |
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