14509-92-3

Basic information

• Product Name: (3β,16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester
• Synonyms: (3β,16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester;Mitraciliatin;Mitraciliatine
• CAS NO: 14509-92-3
• Molecular Formula: C₂₃H₃₀N₂O₄
• Molecular Weight: 398.4953
• Mol File: 14509-92-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 140-141 °C
• Boiling Point: 560.3±50.0 °C(Predicted)
• Appearance: /
• Density: 1.22±0.1 g/cm3(Predicted)
• PKA: 18.35±0.60(Predicted)
• CAS DataBase Reference: (3β,16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3β,16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester(14509-92-3)
• EPA Substance Registry System: (3β,16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester(14509-92-3)

Safety Data

• Hazardous Substances Data: 14509-92-3(Hazardous Substances Data)

Usage

Description

(3β,16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester is a carboline alkaloid derived from the plant Mitragyna ciliata Aubr. et Pellegr. It can be purified through crystallization from Et20-light petroleum, resulting in small, colorless crystals. The compound exhibits characteristic absorption maxima in its ultraviolet spectrum, with peaks at 228 and 292.4 mil, and shoulders at 248.8 and 284 mil. It can be further characterized as the perchlorate salt, which forms light yellow prisms from EtOH-Et20, with a melting point of 229-230°C.

Uses

1. Used in Pharmaceutical Industry:
(3β,16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester is used as a pharmaceutical compound for its potential therapeutic applications. The compound's unique structure and properties make it a promising candidate for the development of new drugs targeting various health conditions.
2. Used in Chemical Research:
In the field of chemical research, (3β,16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester serves as a valuable compound for studying its chemical properties, reactivity, and potential interactions with other molecules. This research can lead to a better understanding of its applications and the development of new synthetic methods or derivatives with improved properties.
3. Used in Drug Delivery Systems:
Similar to gallotannin, (3β,16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester can be employed in drug delivery systems to enhance its bioavailability and therapeutic outcomes. By incorporating the compound into various carriers, such as organic or metallic nanoparticles, its delivery, efficacy, and targeting to specific cells or tissues can be improved.
4. Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, given the compound's potential pharmaceutical applications, it could also be investigated for its anticancer properties. If found to have significant effects on tumor growth and progression, (3β,16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester could be used as an anticancer agent, targeting specific cancer cells and modulating oncological signaling pathways.

References

Beckett, Shellard, Tackie., J. Pharm. Pharmacal. Suppl., 15, 166T (1963)Beckett, Tackie., ibid, 15, 267T (1963)Absolute configuration: Lee, Trager, Beckett., Tetrahedron, 23, 375 (1967)

Upstream product

• 77-78-1 dimethyl sulfate 
• 4837-90-5 4-methoxy-1H-indole 
• 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 
• 4359-77-7 3-ethyl-3-buten-2-one 
• 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 
• 1415662-51-9 (-)-dehydromitragynine 
• 1415662-49-5 C₂₈H₃₆N₂O₆ 
• 1415662-47-3 C₂₆H₃₂N₂O₆ 

Downstream Products

• 174418-82-7 Mitragynine hydroxyindolenine 
• 174418-81-6 O-Acetylmitragynine hydroxyindolenine 
• 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 

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.