18446-73-6

Basic information

• Product Name: tembetarine
• Synonyms: tembetarine;(1S)-1,2,3,4-Tetrahydro-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethylisoquinolin-2-ium
• CAS NO: 18446-73-6
• Molecular Formula: C₂₀H₂₆NO₄
• Molecular Weight: 0
• Mol File: 18446-73-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: tembetarine(CAS DataBase Reference)
• NIST Chemistry Reference: tembetarine(18446-73-6)
• EPA Substance Registry System: tembetarine(18446-73-6)

Safety Data

• Hazardous Substances Data: 18446-73-6(Hazardous Substances Data)

Usage

Description

A quaternary benzylisoquinoline alkaloid, this base is isolated as the crystalline chloride from the bark of Fagara naranjillo (Griseb.) Engl., m.p. 236-7°C; [α]29Db9 + 123.3° (c 0.9, EtOH). The salt gives an ultraviolet spectrum having a single absorption maximum at 284 ffi/J.. The dimethyl ether is identical with Laudano sine methyl ether and the diethyl ether forms a crystalline iodide, m.p. 91-2°C; [α]29Di>8 + 96.2° (c 0.85, CHCI 3).

References

Albonico, Kuck, Deulofeu., Chern. & Ind., 1580 (1964)

InChI:InChI=1/C20H25NO4/c1-21(2)8-7-14-11-20(25-4)18(23)12-15(14)16(21)9-13-5-6-19(24-3)17(22)10-13/h5-6,10-12,16H,7-9H2,1-4H3,(H-,22,23)/p+1/t16-/m0/s1

Upstream product

• 14031-35-7 S-Adenosyl-L-methionine 
• 485-19-8 (+)-(S)-reticuline 

Relevant articles and documents

Isolation and characterization of reticuline N-methyltransferase involved in biosynthesis of the aporphine alkaloid magnoflorine in opium poppy

Benzylisoquinoline alkaloids are a large group of plant-specialized metabolites displaying an array of biological and pharmacological properties associated with numerous structural scaffolds and diverse functional group modification. N-Methylation is one of the most common tailoring reactions, yielding tertiary and quaternary pathway intermediates and products. TwoN-methyltransferases accepting (i) early 1-benzylisoquinoline intermediates possessing a secondary amine and leading to the key branch-point intermediate (S)-reticuline and (ii) downstream protoberberines containing a tertiary amine and forming quaternary intermediates destined for phthalideisoquinolines and antimicrobial benzo[c]phenanthridines were previously characterized. We report the isolation and characterization of a phylogenetically related yet functionally distinct N-methyltransferase (NMT) from opium poppy (Papaver somniferum) that primarily accepts 1-benzylisoquinoline and aporphine substrates possessing a tertiary amine. The preferred substrates were the R and S conformers of reticuline and the aporphine (S)-corytuberine, which are proposed intermediates in the biosynthesis of magnoflorine, a quaternary aporphine alkaloid common in plants. Suppression of the gene encoding reticuline N-methyltransferase (RNMT) using virus-induced gene silencing in opium poppy resulted in a significant decrease in magnoflorine accumulation and a concomitant increase in corytuberine levels in roots. RNMT transcript levels were also most abundant in roots, in contrast to the distribution of transcripts encoding other NMTs, which occur predominantly in aerial plant organs. The characterization of a third functionally unique NMT involved in benzylisoquinoline alkaloid metabolism will facilitate the establishment of structure-function relationships among a large group of related enzymes.