Basic information
- CAS
490-17-5- Standard SMILES
COC(=O)[C@H]1[C@@H](OC(=O)C2C(c3ccccc3)C(C(=O)O[C@H]3C[C@@H]4CC[C@H]([C@H]3C(=O)OC)N4C)C2c2ccccc2)C[C@@H]2CC[C@H]1N2C- InChIKey
BUOSLGZEBFSUDD-XFKBZBJISA-N- Molecular formula
- C38H46N2O8
- Average molar mass
- 658.8 g/mol
- Monoisotopic mass
- 658.32541643
Names & identifiers
- Preferred name
- Bis[(1r,2r,3s,5s)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate
- IUPAC
- bis[(1R,2R,3S,5S)-2-methoxycarbonyl-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate
- English name
- bis[2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate, stereoisomer
- Molecular formula
- C38H46N2O8
- Molecular weight
- 658.78
Names & synonyms
490-17-5a-TruxillineAlpha-TruxillineTruxilline, alpha-bis[(1r,2r,3s,5s)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylateV7VU89LP2KBis[(1R,2R,3S,5S)-2-methoxycarbonyl-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylateCocamine1,3-CYCLOBUTANEDICARBOXYLIC ACID, 2,4-DIPHENYL-, 1,3-BIS((1R,2R,3S,5S)-2-(METHOXYCARBONYL)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL) ESTER, (1.ALPHA.,2.ALPHA.,3.BETA.,4.BETA.)-1,3-Cyclobutanedicarboxylic acid, 2,4-diphenyl-, 1,3-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1.alpha.,2.alpha.,3.beta.,4.beta.)-EINECS 207-707-5Cocaine EP Impurity B
Show more names
α-Truxilline2,4-Diphenyl-1,3-cyclobutanedicarboxylic acid bis[2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] esterbis[2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate, stereoisomer
Properties
Computed structural properties
- XLogP
- 4.6
- Topological polar surface area
- 112 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 12
- Heavy atoms
- 48
- Formal charge
- 0
- Complexity
- 1,110
Experimental & physicochemical properties
CosmeticsEmulsifying
Physicochemical properties
- Melting point
- 80 °C · 80°C
- Density
- 1.296 · 1.296±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- solubility
- Chloroform (Slightly), DMSO (Slightly)
- form
- Solid
- pka
- 8.96 · 8.960±0.10(predicted)
- color
- Off-White to Pale Yellow
- FDA UNII
- 7 VU89LP2K · V7VU89LP2K
- EPA Substance Registry System
- 1 · 1,3-Cyclobutanedicarboxylic acid, 2,4-diphenyl-, bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1.alpha.,2.alpha.,3.beta.,4.beta.)- (490-17-5)
- TSCA
- TSCA listed
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- tsca
- TSCA listed
Chemistry & industry
Uses & manufacturing
Use ClassificationCosmetics -> Emulsifying
General Manufacturing Information1,3-Cyclobutanedicarboxylic acid, 2,4-diphenyl-, 1,3-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1.alpha.,2.alpha.,3.beta.,4.beta.)-: INACTIVE
Applications
DescriptionFrom the leaves of Erythroxylon truxillense Rusby, Hesse isolated an amorphous alkaloid which he designated Cocamine. This was subsequently shown by Liebermann to be a mixture of two isomeric bases and, although the pure alkaloids have not yet been obtained from the alkaloidal mixture owing to difficulties in their separation, each has been prepared synthetically. This particular alkaloid is an amorphous white powder which is soluble in all organic solvents except light petroleum and also insoluble in H20. Solutions of the base are alllaevorotatory and have an intensely bitter taste. Acid hydrolysis with dilute HCl yields MeOH, (-)-ecgonine and Q-truxillic acid, m.p. 228°C. The alkaloid is synthesized by the action of α-truxillic anhydride on (-)-ecgonine followed by methylation of the resulting α-truxilloylecgonine.
Uses-Truxillin is an alkaloid found in coca leaves. It is an impurity of illicit Cocaine (C633500), which inhibits the dopamine, norepinephrine, and serotonin transporters.
Suppliers5 total
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
珠海安哲生物科技有限公司13169972583 · [email protected]
艾吉析科技（上海）有限公司17717235263 17717235263 · [email protected]
Related reactions
0 records
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Compound notes
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