2688-77-9

Basic information

• Product Name: laudanosine
• Synonyms: (+)-(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;Nsc 35045
• CAS NO: 2688-77-9
• Molecular Formula: C₂₁H₂₇NO₄
• Molecular Weight: 357.44338
• EINECS: 220-253-2
• Product Categories: Alkaloids;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Aromatics, Chiral Reagents, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 2688-77-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 89°
• Boiling Point: 490.07°C (rough estimate)
• Flash Point: 131.2°C
• Appearance: /
• Density: 1.1729 (rough estimate)
• Vapor Pressure: 6.19E-09mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly, Sonicated)
• PKA: 7.80±0.40(Predicted)
• CAS DataBase Reference: laudanosine(CAS DataBase Reference)
• NIST Chemistry Reference: laudanosine(2688-77-9)
• EPA Substance Registry System: laudanosine(2688-77-9)

Safety Data

• Hazardous Substances Data: 2688-77-9(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3/t17-/m0/s1

Upstream product

• 1699-51-0 laudanosine 
• 186581-53-3 diazomethane 
• 13452-22-7 (S)-(+)-1-(3',4'-dimethoxybenzyl)-6-hydroxy-7-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline 
• 87183-78-6 (+)-O,O,O-Trimethylvateamine 
• 102922-34-9 2-[(4S)-4,5-dihydro-4-(1-methylethyl)-2-oxazolyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 2258-42-6 formyl acetic anhydride 
• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 
• 408331-39-5 6,7-dimethoxy-1-(3,4-dimethoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol 
• 77-95-2 1,3,4,5-tetrahydroxy-cyclohexanecarboxylic acid 
• 136114-05-1 N-[((1R,2S,5R)-8-phenylmenthoxy)carbonyl]-1-(4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 50-00-0 formaldehyd 
• 4747-98-2 S-(-)-Norlaudanosine 
• 106647-99-8 (+)-threo-N-(ethoxycarbonyl)hydroxynorlaudanosine 
• 57651-56-6 (S)-1-<(3,4-Dimethoxyphenyl)methyl>-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 1699-51-0 laudanosine 
• 85-63-2 (R)-laudanosine 
• 23669-24-1 (+/-)-N-ethyl-Laudanosine iodide 
• 26952-97-6 2,3,6,7-tetramethoxy-9,10-dihydro-anthracene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 475-81-0 glaucine 

Relevant articles and documents

Asymmetric total synthesis of (?)-javaberine A and (?)-epi-javaberine A based on catalytic intramolecular hydroamination of N-methyl-2-(2-styrylaryl)ethylamine

Asymmetric total synthesis of (?)-javaberine A and its epimer was achieved by utilizing two methods for isoquinoline synthesis, asymmetric hydroamination of N-methyl-2-(2-styrylaryl)ethylamine and Bischler-Napieralski cyclization. Intramolecular asymmetric hydroamination of N-methyl aminoalkene 4 was catalyzed by lithium amide–chiral bisoxazoline to give tetrahydroisoquinoline (S)-laudanosine with good enantioselectivity in excellent yield. N-Demethylation of (S)-laudanosine was accomplished by Polonovski-type reaction to give (S)-norlaudanosine. Condensation of (S)-norlaudanosine with homoveratric acid, and subsequent Bischler-Napieralski cyclization, LiAlH4 reduction, and O-demethylation furnished (8R,14S)-(?)-javaberine A, corresponding to antipode of natural javaberine A. (8S,14S)-(?)-Javaberine A, which corresponds to C14-epimer of natural javaberine A, was also successfully synthesized.

Total synthesis of 8-epi-javaberine A and javaberine A

The total synthesis of berberine alkaloid javaberine A was examined. The B/C ring of berberine was successfully constructed by sequential Bischler-Napieralski cyclization-reduction protocols, and final demethylation afforded both javaberine A and its epimer.

Enantioselective synthesis of tetrahydroprotoberberines and bisbenzylisoquinoline alkaloids from a deprotonated α-aminonitrile

Under controlled conditions, 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline- 1-carbonitrile can be quantitatively deprotonated in the α-position. Its alkylation directly furnishes 3,4-dihydroisoquinolines which can serve as starting materials for the preparation of various alkaloids. Here, the preparation of the benzylisoquinolines (+)-laudanidine, (+)-armepavine, and (+)-laudanosine as well as the tetrahydroprotoberberines ( - )-corytenchine and ( - )-tetrahydropseudoepiberberine using Noyori's asymmetric transfer hydrogenation are described. The dimeric alkaloids (+)-O-methylthalibrine and (+)-tetramethylmagnolamine were obtained from nonracemic precursors in Ullmann diaryl ether syntheses.