85-63-2

Basic information

• Product Name: (-)-laudanosine
• Synonyms: (R)-Laudanosine; N-methyl-1,2-dihydropapaverine; (-)-(1R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline; (R)-1-(3',4'-dimethoxybenzyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; (+)-(R)-laudanosine
• CAS NO: 85-63-2
• Molecular Formula: C₂₁H₂₇NO₄
• Molecular Weight: 357.44300
• Mol File: 85-63-2.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: (-)-laudanosine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-laudanosine(85-63-2)
• EPA Substance Registry System: (-)-laudanosine(85-63-2)

Safety Data

• Hazardous Substances Data: 85-63-2(Hazardous Substances Data)

Usage

Description

(-)-Laudanosine is a chemical compound belonging to the benzylisoquinoline alkaloid class. It is a natural product derived from opium poppy (Papaver somniferum) and other related plant species. (-)-laudanosine has been studied for its potential pharmaceutical properties, such as its use as a neuromuscular blocking agent, its sedative effects, and its anesthetic properties. It also shows promise in affecting the central nervous system, which may have implications for the treatment of neurological disorders. However, further research is necessary to fully understand its pharmacological properties and potential therapeutic applications.

Uses

Used in Pharmaceutical Industry:
(-)-Laudanosine is used as a neuromuscular blocking agent for its ability to induce muscle paralysis, which can be beneficial in surgical procedures.
(-)-Laudanosine is used as a sedative for its potential calming effects on the central nervous system, which may help in managing anxiety and promoting relaxation.
Used in Anesthesia Development:
(-)-Laudanosine is used in the research and development of new anesthetic drugs due to its anesthetic properties, which can provide pain relief and induce a state of unconsciousness during medical procedures.
Used in Neurological Disorder Treatment:
(-)-Laudanosine is used in the study and potential treatment of neurological disorders due to its effects on the central nervous system, which may offer therapeutic benefits for conditions affecting the brain and nervous system.

Upstream product

• 1699-51-0 laudanosine 
• 61348-95-6 (Z)-1-<(3,4-Dimethoxyphenyl)methylene>-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 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 
• 50-00-0 formaldehyd 
• 50896-90-7 (-) N-norlaudanosine 
• 136114-05-1 N-[((1R,2S,5R)-8-phenylmenthoxy)carbonyl]-1-(4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 4525-33-1 dimethyl dicarbonate 
• 408331-39-5 6,7-dimethoxy-1-(3,4-dimethoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol 
• 6957-27-3 3,4-dihydropapaverine 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 6429-04-5 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride 

Downstream Products

• 475-81-0 (-)-(R)-glaucine 
• 37569-03-2 2'-(β-N-Methyl-N-ethoxycarbonyl)aminoethyl-3,3',4,4'-tetramethoxystilben 

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.

Organocatalytic Enantioselective Pictet-Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids

(Figure Presented) A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.

Method of Analyzing Optical Isomers or Method of Resolving the Same

Provided are a method of quickly and simply confirming the success or failure of resolution of optical isomers with the use of a column for resolving optical isomers and a method of simply designing the conditions of the eluent composition under isocratic elution conditions. In resolving optical isomers, the success or failure of the resolution can be simply and quickly confirmed by employing an HPLC gradient elution analysis method with the use of a column for resolving optical isomers. When the resolution is successfully conducted, the eluent composition under isocratic elution conditions can be estimated from the elution time in the gradient elution analysis.