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ChemicalBook >> CAS DataBase List >>1,2-Cyclobutanedicarboxylic acid, 3,4-diphenyl-, 1,2-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1R,2S,3R,4S)-

1,2-Cyclobutanedicarboxylic acid, 3,4-diphenyl-, 1,2-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1R,2S,3R,4S)-

1,2-Cyclobutanedicarboxylic acid, 3,4-diphenyl-, 1,2-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1R,2S,3R,4S)- Structure
1,2-Cyclobutanedicarboxylic acid, 3,4-diphenyl-, 1,2-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1R,2S,3R,4S)- structure
CAS No.
490-15-3
Chemical Name:
1,2-Cyclobutanedicarboxylic acid, 3,4-diphenyl-, 1,2-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1R,2S,3R,4S)-
Synonyms
β-Truxilline;Diclazuril Impurity?1 (Diclazuril EP Impurity?A);bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl](1r,2c,3t,4t)-3,4-diphenylcyclobutane-1,2-dicarboxylate(β-truxilline);1,2-Cyclobutanedicarboxylic acid, 3,4-diphenyl-, 1,2-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1R,2S,3R,4S)-
CBNumber:
CB44833156
Molecular Formula:
C38H46N2O8
Molecular Weight:
658.78
MDL Number:
MOL File:
490-15-3.mol
Last updated:2023-05-15 10:43:18
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1,2-Cyclobutanedicarboxylic acid, 3,4-diphenyl-, 1,2-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1R,2S,3R,4S)- Properties

Melting point Decomposes at 120°C
Density 1.29±0.1 g/cm3(Predicted)
pka 9.09±0.60(Predicted)
FDA UNII X4WN4Y5R5N

1,2-Cyclobutanedicarboxylic acid, 3,4-diphenyl-, 1,2-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1R,2S,3R,4S)- Chemical Properties,Uses,Production

Description

This isomeric alkaloid from the leaf extract of Erythroxylon truxillense Rusby sinters at 45°C and decomposes above 120°C. It is laevorotatory with [α]D - 29.3°. On acid hydrolysis it yields MeOH, (-)-ecgonine and {3-truxillic acid, m.p. 206°C and may be synthesized in a similar manner to the preceding base.

Uses

β-Truxilline is an alkaloid found in coca leaves. It is an impurity of illicit Cocaine (C633500), which inhibits the dopamine, norepinephrine, and serotonin transporters.

References

Hesse., Pharm. Zeit., 407,668 (1887)
Liebermann., Ber., 21,2342 (1888)
Hesse., ibid, 22,665 (1889)
Liebermann, Drory., ibid, 22,682 (1889)

1,2-Cyclobutanedicarboxylic acid, 3,4-diphenyl-, 1,2-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1R,2S,3R,4S)- Preparation Products And Raw materials

Raw materials

Preparation Products

1,2-Cyclobutanedicarboxylic acid, 3,4-diphenyl-, 1,2-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1R,2S,3R,4S)- Suppliers

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1,2-Cyclobutanedicarboxylic acid, 3,4-diphenyl-, 1,2-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1R,2S,3R,4S)- β-Truxilline bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl](1r,2c,3t,4t)-3,4-diphenylcyclobutane-1,2-dicarboxylate(β-truxilline) Diclazuril Impurity?1 (Diclazuril EP Impurity?A) 490-15-3