6202-22-8

Basic information

• Product Name: MITRAGYNINE
• Synonyms: Kratom;Methyl (16E,20β)-9,17-dimethoxycoryn-16-en-16-carboxylate
• CAS NO: 6202-22-8
• Molecular Formula: C₂₃H₃₀N₂O₄
• Molecular Weight: 398.4953
• Mol File: 6202-22-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 560.3°Cat760mmHg
• Flash Point: 292.7°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 1.39E-12mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: MITRAGYNINE(CAS DataBase Reference)
• NIST Chemistry Reference: MITRAGYNINE(6202-22-8)
• EPA Substance Registry System: MITRAGYNINE(6202-22-8)

Safety Data

• Hazardous Substances Data: 6202-22-8(Hazardous Substances Data)

Usage

General Description

MITRAGYNINE is the most abundant active alkaloid found in the leaves of the Southeast Asian plant, Mitragyna speciosa, also known as kratom. It acts as a partial agonist at the mu-opioid receptors, producing both stimulant and sedative effects in low and high doses, respectively. MITRAGYNINE has been studied for its potential medicinal uses, including as a treatment for opioid withdrawal and chronic pain. However, it also carries a risk of dependence and addiction, and its safety and efficacy are still under debate. Thus, its legal status and regulation vary widely across different countries and regions.

InChI:InChI=1/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16+,19+/m1/s1

Upstream product

• 173102-63-1 (E)-2-[(2S,12bS)-3-Eth-(Z)-ylidene-8-methoxy-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl]-3-methoxy-acrylic acid methyl ester 
• 4837-90-5 4-methoxy-1H-indole 
• 77-78-1 dimethyl sulfate 
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• 99115-96-5 3-ethyl-4-hydroxy-2-butanone 
• 210359-35-6 2-(2-methyl-1,3-dioxolan-2-yl)butan-1-ol 
• 51756-08-2 methyl 2-ethyl-3-oxobutanoate 
• 285983-16-6 N-(2-(4-methoxy-1H-indol-3-yl)ethyl)formamide 
• 3610-35-3 4-methoxytryptamine 
• 83788-92-5 (E)-4-methoxy-3-(2-nitrovinyl)-1H-indole 
• 90734-97-7 4-methoxyindole-3-carboxaldehyde 
• 951327-93-8 methyl 2-((2R,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate 
• 149-73-5 trimethyl orthoformate 
• 173102-62-0 (Z)-2-[(2S,12bS)-3-Eth-(Z)-ylidene-8-methoxy-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl]-3-hydroxy-acrylic acid methyl ester 

Downstream Products

• 29472-77-3 gambirine 
• 23407-35-4 methyl (E)-2-((2S,3S,12bS)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-methoxyacrylate 
• 174418-82-7 Mitragynine hydroxyindolenine 
• 174418-81-6 O-Acetylmitragynine hydroxyindolenine 

Relevant articles and documents

MITRAGYNINE ANALOGS FOR THE TREATMENT OF PAIN, MOOD DISORDERS AND SUBSTANCE USE DISORDERS

The present invention provides a compound having the structure (I): or a pharmaceutically acceptable salt or ester thereof, and a method of treating a subject afflicted with pain a depressive disorder, a mood disorder or an anxiety disorder by administering the compound to the subject.

Synthetic and Receptor Signaling Explorations of the Mitragyna Alkaloids: Mitragynine as an Atypical Molecular Framework for Opioid Receptor Modulators

Mu-opioid receptor agonists represent mainstays of pain management. However, the therapeutic use of these agents is associated with serious side effects, including potentially lethal respiratory depression. Accordingly, there is a longstanding interest in the development of new opioid analgesics with improved therapeutic profiles. The alkaloids of the Southeast Asian plant Mitragyna speciosa, represented by the prototypical member mitragynine, are an unusual class of opioid receptor modulators with distinct pharmacological properties. Here we describe the first receptor-level functional characterization of mitragynine and related natural alkaloids at the human mu-, kappa-, and delta-opioid receptors. These results show that mitragynine and the oxidized analogue 7-hydroxymitragynine, are partial agonists of the human mu-opioid receptor and competitive antagonists at the kappa- and delta-opioid receptors. We also show that mitragynine and 7-hydroxymitragynine are G-protein-biased agonists of the mu-opioid receptor, which do not recruit β-arrestin following receptor activation. Therefore, the Mitragyna alkaloid scaffold represents a novel framework for the development of functionally biased opioid modulators, which may exhibit improved therapeutic profiles. Also presented is an enantioselective total synthesis of both (-)-mitragynine and its unnatural enantiomer, (+)-mitragynine, employing a proline-catalyzed Mannich-Michael reaction sequence as the key transformation. Pharmacological evaluation of (+)-mitragynine revealed its much weaker opioid activity. Likewise, the intermediates and chemical transformations developed in the total synthesis allowed the elucidation of previously unexplored structure-activity relationships (SAR) within the Mitragyna scaffold. Molecular docking studies, in combination with the observed chemical SAR, suggest that Mitragyna alkaloids adopt a binding pose at the mu-opioid receptor that is distinct from that of classical opioids.

Indole Alkaloid Derivatives Having Opioid Receptor Agonistic Effect, and Therapeutic Compositions and Methods Relating to Same

Indole alkaloid derivatives having an opioid receptor agonistic effect, their synthesis, and therapeutic compositions containing these derivatives, and methods of treating conditions with these compounds and therapeutic compositions, are provided.