490-53-9

Basic information

• Product Name: (R)-(+)-Carnegine
• Synonyms: (+)-Carnegine;(1R)-1,2,3,4-Tetrahydro-1β,2-dimethyl-6,7-dimethoxyisoquinoline;(1R)-1,2-Dimethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;(1R)-1β,2-Dimethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;(R)-(-)-Carnegine;(R)-(+)-Carnegine
• CAS NO: 490-53-9
• Molecular Formula: C₁₃H₁₉NO₂
• Molecular Weight: 221.2955
• Mol File: 490-53-9.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 362.36°C (rough estimate)
• Flash Point: 100.9°C
• Appearance: /
• Density: 1.0451 (rough estimate)
• Vapor Pressure: 0.00102mmHg at 25°C
• Refractive Index: 1.5175 (estimate)
• CAS DataBase Reference: (R)-(+)-Carnegine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-Carnegine(490-53-9)
• EPA Substance Registry System: (R)-(+)-Carnegine(490-53-9)

Safety Data

• Hazardous Substances Data: 490-53-9(Hazardous Substances Data)

Usage

General Description

(R)-(+)-Carnitine is a naturally occurring compound in the body that plays a crucial role in energy production and metabolism. It is an amino acid derivative that is involved in the transport of fatty acids into the mitochondria for energy production. (R)-(+)-Carnitine is also known for its antioxidant properties and its ability to support heart, brain, and muscle health. Supplements of (R)-(+)-Carnitine have been used to improve exercise performance, aid in weight loss, and manage certain medical conditions such as angina and peripheral arterial disease. Additionally, it has been studied for its potential therapeutic benefits in treating conditions such as diabetes, chronic fatigue syndrome, and other metabolic disorders.

InChI:InChI=1/C13H19NO2/c1-9-11-8-13(16-4)12(15-3)7-10(11)5-6-14(9)2/h7-9H,5-6H2,1-4H3/t9-/m0/s1

Upstream product

• 50-00-0 formaldehyd 
• 493-48-1 (6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline) 
• 186581-53-3 diazomethane 
• 525-72-4 (+/-)-salsolinol 
• 6075-61-2 6,7-Dimethoxy-1,2-dimethylisoquinoliniumiodide 
• 17104-28-8 1-methyl-6,7-dimethoxy-2-methyl-3,4-dihydro-isoquinolinium iodide 
• 485-80-3 S-adenosyl-L-methionine 
• 16620-96-5 2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 32749-01-2 3,4-dihydro-6,7-dimethoxy-2-methylisoquinolinium 
• 75-16-1 methylmagnesium bromide 
• 127119-08-8 3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester 
• 140368-04-3 tert-butyl 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 93631-46-0 6,7-Dimethoxy-2-ethoxycarbonyl-1-methyl-1,2-dihydroisoquinaldonitrile 

Downstream Products

• 51745-28-9 (R)-(+)-carnegine 

Relevant articles and documents

Structure and Biocatalytic Scope of Coclaurine N-Methyltransferase

Benzylisoquinoline alkaloids (BIAs) are a structurally diverse family of plant secondary metabolites, which have been exploited to develop analgesics, antibiotics, antitumor agents, and other therapeutic agents. Biosynthesis of BIAs proceeds via a common pathway from tyrosine to (S)-reticulene at which point the pathway diverges. Coclaurine N-methyltransferase (CNMT) is a key enzyme in the pathway to (S)-reticulene, installing the N-methyl substituent that is essential for the bioactivity of many BIAs. In this paper, we describe the first crystal structure of CNMT which, along with mutagenesis studies, defines the enzymes active site architecture. The specificity of CNMT was also explored with a range of natural and synthetic substrates as well as co-factor analogues. Knowledge from this study could be used to generate improved CNMT variants required to produce BIAs or synthetic derivatives.

Synthesis of 1-substituted tetrahydroisoquinolines by lithiation and electrophilic quenching guided by in situ IR and NMR spectroscopy and application to the synthesis of salsolidine, carnegine and laudanosine

The lithiation of N-tert-butoxycarbonyl (N-Boc)-1,2,3,4- tetrahydroisoquinoline was optimized by in situ IR (ReactIR) spectroscopy. Optimum conditions were found by using n-butyllithium in THF at -50 °C for less than 5 min. The intermediate organolithium was quenched with electrophiles to give 1-substituted 1,2,3,4-tetrahydroisoquinolines. Monitoring the lithiation by IR or NMR spectroscopy showed that one rotamer reacts quickly and the barrier to rotation of the Boc group was determined by variable-temperature NMR spectroscopy and found to be about 60.8 kJ mol-1, equating to a half-life for rotation of approximately 30 s at -50 °C. The use of (-)-sparteine as a ligand led to low levels of enantioselectivity after electrophilic quenching and the "poor man's Hoffmann test" indicated that the organolithium was configurationally unstable. The chemistry was applied to N-Boc-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline and led to the efficient synthesis of the racemic alkaloids salsolidine, carnegine, norlaudanosine and laudanosine. Copyright

Transfer hydrogenation of isoquinolinium salts catalyzed by a rhodium complex

Regio- and chemoselective transfer hydrogenation of isoquinolinium salts catalyzed by [Cp*RhCl2]2 using HCOOH-Et3N (5:2) as a hydrogen source was realized. A variety of N-methyl- and N-benzyl-1,2,3,4-tetrahydroisoquinoline