laudanosine

laudanosine  Structure
CAS No.
2688-77-9
Chemical Name:
laudanosine
Synonyms
Nsc 35045;Einecs 220-253-2;(+)-(S)-Laudanosine;Cisatracurium Besylate Impurity 49;(S)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline;(1S)-1,2,3,4-Tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline;[1S,(+)]-1-[(3,4-Dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline;Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (1S)-
CBNumber:
CB7897724
Molecular Formula:
C21H27NO4
Molecular Weight:
357.44
MOL File:
2688-77-9.mol
Modify Date:
2023/6/8 9:02:58

laudanosine Properties

Melting point 89°
alpha D16 +106° (c = 1.6 in 97% alc); D16 +130° (chloroform); D22 +52.2 ±1.3° (chloroform); D20 +82.5° (ethanol)
Boiling point 490.07°C (rough estimate)
Density 1.1729 (rough estimate)
refractive index 1.5614 (estimate)
storage temp. -20°C Freezer
solubility Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly, Sonicated)
form White to Pale Beige
pka 7.80±0.40(Predicted)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
NFPA 704
0
4 0

laudanosine Chemical Properties,Uses,Production

Uses

Laudanosine is 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.

Purification Methods

Crystallise these from EtOH. The (±)-picrate crystallises from EtOH with m 177-178o. The (-)-isomer has m 83-85o and

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Nsc 35045 (+)-(S)-Laudanosine (1S)-1,2,3,4-Tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline [1S,(+)]-1-[(3,4-Dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline Einecs 220-253-2 Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (1S)- (S)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline Cisatracurium Besylate Impurity 49 2688-77-9 Alkaloids Aromatics Chiral Reagents Heterocycles Intermediates & Fine Chemicals Metabolites & Impurities Pharmaceuticals Aromatics, Chiral Reagents, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals