23407-35-4

Usage

Uses

Used in Pharmaceutical Industry:
Corynantheidine is used as an immunosuppressive agent for its ability to modulate the immune system. This property makes it a valuable compound in the development of treatments for autoimmune diseases and conditions that require immune system regulation.
Used in Traditional Medicine:
Corynantheidine has been traditionally used in various medicinal practices, particularly in African traditional medicine, for its potential therapeutic effects. Its immunosuppressive activity contributes to its use in treating specific ailments and maintaining overall health.
Used in Drug Development:
Due to its immunosuppressive properties, corynantheidine is also utilized in the development of new drugs and therapies. Researchers are exploring its potential in creating novel pharmaceuticals that can target specific immune-related conditions more effectively.

InChI:InChI=1/C22H28N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h5-8,13-14,17,20,23H,4,9-12H2,1-3H3/b18-13+/t14-,17+,20+/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 26076-15-3 2-((2R,3S,12bS)-3-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-3-oxo-propionic acid methyl ester 
• 93630-84-3 2-((1S,2S)-2-Ethyl-3,4-dihydroxy-5-methoxycarbonyl-cyclopentyl)-malonic acid dimethyl ester 
• 295788-84-0 N_b-(Z-2'-iodo-2'-butenyl)tryptophan benzyl ester 
• 71657-70-0 (E)-2-((2S,3S,12bS)-3-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-3-hydroxy-acrylic acid methyl ester 
• 1395097-38-7 C₁₈H₂₂N₂O₃ 
• 1395097-37-6 C₂₄H₂₅N₃O₇S 
• 913524-95-5 C₂₂H₂₁N₃O₆S 
• 1395097-36-5 C₂₇H₂₉N₃O₈S 
• 1395097-35-4 C₂₀H₁₉N₃O₆S 
• 19005-93-7 1H-indol-2-ylcarboxaldehyde 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 82513-42-6 1-benzenesulfonyl-17-methoxy-5α-cyano-16ζ,17-2α,7α-tetrahydrocorynantheidine 
• 82503-78-4 1-benzenesulfonyl-17-methoxy-16ζ,17-2α,7α-tetrahydrocorynantheidine 
• 82510-86-9 (2S,3S)-12-Benzenesulfonyl-3-ethyl-1,3,4,7,7a,12,12a,12b-octahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine-13-carbaldehyde 
• 82510-87-0 1-benzene-sulfonyl-2α,7α-20α,19-tetrahydro-10-deoxysarpagine 

Relevant academic research and scientific papers

Kratom Alkaloids as Probes for Opioid Receptor Function: Pharmacological Characterization of Minor Indole and Oxindole Alkaloids from Kratom

Dry leaves of kratom (mitragyna speciosa) are anecdotally consumed as pain relievers and antidotes against opioid withdrawal and alcohol use disorders. There are at least 54 alkaloids in kratom; however, investigations to date have focused around mitragynine, 7-hydroxy mitragynine (7OH), and mitragynine pseudoindoxyl (MP). Herein, we probe a few minor indole and oxindole based alkaloids, reporting the receptor affinity, G-protein activity, and βarrestin-2 signaling of corynantheidine, corynoxine, corynoxine B, mitraciliatine, and isopaynantheine at mouse and human opioid receptors. We identify corynantheidine as a mu opioid receptor (MOR) partial agonist, whereas its oxindole derivative corynoxine was an MOR full agonist. Similarly, another alkaloid mitraciliatine was found to be an MOR partial agonist, while isopaynantheine was a KOR agonist which showed reduced βarrestin-2 recruitment. Corynantheidine, corynoxine, and mitraciliatine showed MOR dependent antinociception in mice, but mitraciliatine and corynoxine displayed attenuated respiratory depression and hyperlocomotion compared to the prototypic MOR agonist morphine in vivo when administered supraspinally. Isopaynantheine on the other hand was identified as the first kratom derived KOR agonist in vivo. While these minor alkaloids are unlikely to play the majority role in the biological actions of kratom, they represent excellent starting points for further diversification as well as distinct efficacy and signaling profiles with which to probe opioid actions in vivo.

DEUTERATED MITRAGYNINE ANALOGS AS SAFER OPIOID MODULATORS IN THE MITRAGYNINE CLASS

The present invention provides a compound having the structure: or a pharmaceutically acceptable salt or ester thereof, and methods of using the compound to treat pain, depressive disorders, mood disorders, anxiety disorders, opioid use disorder, and opioid withdrawal symptoms.

MITRAGYNINE ANALOGS AND USES THEREOF

Described herein are compounds of Formulae (I')-(II'), compounds of Formulae (I)- (II) and pharmaceutically acceptable salts thereof. Compounds of the present invention are useful for modulating opioid receptor activity. The provided compounds may have both agonistic and antagonistic effect on one or more opioid receptors. Methods of using the compounds for treating or managing pain are also described.

Total synthesis of (±)-hirsutine: Application of phosphine-catalyzed imine-allene [4 + 2] annulation

The total synthesis of the indole alkaloid hirsutine has been achieved, with a key step being the application of our phosphine-catalyzed [4 + 2] annulation of an imine with ethyl α-methylallenoate. From commercially available indole-2-carboxaldehyde, the target was synthesized in 14 steps and 6.7% overall yield.

Enantioselective syntheses of corynanthe alkaloids by Chiral Br?nsted acid and palladium catalysis

Synergistic catalysis: Three indole alkaloids (-)-corynantheidine, (+)-corynantheine and (+)-dihydro-corynantheine were prepared following a short and common strategy based on the binol phosphoric acid catalyzed enantioselective Pictet-Spengler reaction,

Total synthesis of (-)-corynantheidine by nickel-catalyzed carboxylative cyclization of enynes

The total synthesis of (-)-corynantheidine has been achieved through Ni0-mediated carboxylative cyclization as the key reaction step with incorporation of CO2, and this cyclization was also successfully expanded to the catalytic reac

Preparation of (±)-hirsutine and (±)-3-isocorynantheidine

Preparation of indole alkaloids (±)-hirsutine (1) and (±)-3- isocorynantheidine (2) is described.

Stereoselective Total Synthesis of (+/-)-Hirsutine and Related Corynanthe Alkaloids

In a completely stereoselective sequence, an analogue of dihydrosecologanin aglucone has been synthesised via a novel cyclopentenedione dimer and converted into tetracyclic indole alkaloids.