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Tigloyltropeine

CAS# 495-83-0

Tigloyltropeine

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Chemical structure

Tigloyltropeine

3D structure

Chemical Properties of Tigloyltropeine

Cas No. 495-83-0 SDF Download SDF
PubChem ID 5281865 Appearance Oil
Formula C13H21NO2 M.Wt 223.31
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Tigloyl pseudotropine; Tiglylpseudotropine; Tiglyssin
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (8-methyl-8-azabicyclo[3.2.1]octan-3-yl) (E)-2-methylbut-2-enoate
SMILES CC=C(C)C(=O)OC1CC2CCC(C1)N2C
Standard InChIKey UVHGSMZRSVGWDJ-RUDMXATFSA-N
Standard InChI InChI=1S/C13H21NO2/c1-4-9(2)13(15)16-12-7-10-5-6-11(8-12)14(10)3/h4,10-12H,5-8H2,1-3H3/b9-4+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Protocol of Tigloyltropeine

Structure Identification
J Ethnopharmacol. 1995 Dec 1;49(2):81-9.

Alkaloids of Datura ferox from Argentina.[Pubmed: 8847888]

Chromatographic procedures (HPLC, GC-MS) are outlined in this paper for the analysis of alkaloids in poisonous Datura ferox seeds of Argentina, from which previously only quantitative analysis for scopolamine was known.
METHODS AND RESULTS:
Five additional tropane alkaloids are now identified as 3 alpha-tigloyloxytropane (Tigloyltropeine), 3-phenylacetoxy-6 beta,7 beta-epoxytropane (3-phenylacetoxyscopine), aposcopolamine (apohyoscine), 7 beta-hydroxy-6 beta-propenyloxy-3 alpha-tropoyloxytropane, traces of 7 beta-hydroxy-6 beta-isovaleroyloxy-3 alpha-tigloyloxytropane and a pyrrolidine alkaloid, hygrine.
CONCLUSIONS:
Two new structures, 3-phenylacetoxy-6 beta,7 beta-epoxytropane (3-phenylacetoxyscopine) and 7 beta-hydroxy-6 beta-propenyloxy-3 alpha-tropolyoxytropane, are proposed on the basis of their spectra. Hyoscyamine, nicotine and tropane N-oxides were not detected in all samples studied.

Tigloyltropeine Dilution Calculator

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Tigloyltropeine Molarity Calculator

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Preparing Stock Solutions of Tigloyltropeine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.4781 mL 22.3904 mL 44.7808 mL 89.5616 mL 111.952 mL
5 mM 0.8956 mL 4.4781 mL 8.9562 mL 17.9123 mL 22.3904 mL
10 mM 0.4478 mL 2.239 mL 4.4781 mL 8.9562 mL 11.1952 mL
50 mM 0.0896 mL 0.4478 mL 0.8956 mL 1.7912 mL 2.239 mL
100 mM 0.0448 mL 0.2239 mL 0.4478 mL 0.8956 mL 1.1195 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Tigloyltropeine

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].

References:
[1]. Sanghvi I, et al. Pharmacology of a potential anti-Parkinson agent: tigloidine. Eur J Pharmacol. 1968 Oct;4(3):246-53.

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References on Tigloyltropeine

Alkaloids of Datura ferox from Argentina.[Pubmed:8847888]

J Ethnopharmacol. 1995 Dec 1;49(2):81-9.

Chromatographic procedures (HPLC, GC-MS) are outlined in this paper for the analysis of alkaloids in poisonous Datura ferox seeds of Argentina, from which previously only quantitative analysis for scopolamine was known. Five additional tropane alkaloids are now identified as 3 alpha-tigloyloxytropane (Tigloyltropeine), 3-phenylacetoxy-6 beta,7 beta-epoxytropane (3-phenylacetoxyscopine), aposcopolamine (apohyoscine), 7 beta-hydroxy-6 beta-propenyloxy-3 alpha-tropoyloxytropane, traces of 7 beta-hydroxy-6 beta-isovaleroyloxy-3 alpha-tigloyloxytropane and a pyrrolidine alkaloid, hygrine. Two new structures, 3-phenylacetoxy-6 beta,7 beta-epoxytropane (3-phenylacetoxyscopine) and 7 beta-hydroxy-6 beta-propenyloxy-3 alpha-tropolyoxytropane, are proposed on the basis of their spectra. Hyoscyamine, nicotine and tropane N-oxides were not detected in all samples studied.

Description

Tigloidin is an analogue of atropine, with anticholinergic activity.

Keywords:

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