Laudanosine, (R)-
Basic information
- CAS
85-63-2- Standard SMILES
COc1ccc(C[C@@H]2c3cc(OC)c(OC)cc3CCN2C)cc1OC- InChIKey
KGPAYJZAMGEDIQ-QGZVFWFLSA-N- Molecular formula
- C21H27NO4
- Average molar mass
- 357.4 g/mol
- Monoisotopic mass
- 357.19400834
Overview
(R)-laudanosine is a benzylisoquinoline alkaloid that is (R)-tetrahydropapaverine in which the amino hydrogen has been replaced by a methyl group. It is a benzylisoquinoline alkaloid, a benzyltetrahydroisoquinoline, an aromatic ether, a polyether and a tertiary amino compound. It is functionally related to a (R)-tetrahydropapaverine. It is a conjugate base of a (R)-laudanosine(1+).
Names & identifiers
- Preferred name
- Laudanosine, (R)-
- IUPAC
- (1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
- English name
- (R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
- Molecular formula
- C21H27NO4
- Molecular weight
- 357.44
Names & synonyms
(R)-laudanosine85-63-2(-)-LaudanosineD-LaudanosineO-MethyllaudanidineLaudanosine, (R)-EO6NL5AZ5Z(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolineCHEBI:136734(R)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinolineIsoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (1R)-(1R)-1-((3,4-dimethoxyphenyl)methyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
Show more names
Impurities of atracurium391cis-Atracurium EP Impurity C(R)-1-(3,4-dimethoxybenzyl)-AtracuriuM Besylate iMpurity CCisatracurium Besilate Impurity 3Cisatracurium Besilate EP Impurity CCisatracurium Besilate EP Impurity C (R-Laudanosine)
RefChem:1088370UNII-EO6NL5AZ5Z(R)-Laudanosine [USP](1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolineCisatracurium Besylate EP Impurity C(R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline(R)-N-methyltetrahydropapaverine(R)-(-)-laudanosine
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 40.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 434
Physicochemical properties
- solubility
- Chloroform (Slightly), DMSO (Slightly, Sonicated), Ethanol (Slightly), Methanol
- form
- Solid
- color
- White to Off-White
- FDA UNII
- 6 NL5AZ5Z · EO6NL5AZ5Z
Chemistry & industry
Applications
Uses(R)-Laudanosine is an isomer of (S)-Laudanosine (L178525), a metabolite of the neuromuscular-blocking drugs Atracurium (A794500) and Cisatracurium (C496700) with potentially toxic systemic effects. It crosses the blood-brain barrier and may cause excitement and seizure activity.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: (R)-laudanosine is a benzylisoquinoline alkaloid that is (R)-tetrahydropapaverine in which the amino hydrogen has been replaced by a methyl group It is a polyether, a benzylisoquinoline alkaloid, a benzyltetrahydroisoquinoline, an aromatic ether and a tertiary amino compound. It is functionally related to a (R)-tetrahydropapaverine. It is a conjugate base of a (R)-laudanosine(1+).
Related reactions
1 records
Compound notes
Loading…