4098-40-2

Basic information

• Product Name: MITRAGYNINE PICRATE
• Synonyms: 9-Methoxycorynantheidine;MITRAGYNINE(SH);Mitragynin;MITRAGYNINE(P);(αE,2S,3S,12bS)-3-Ethyl-1,2,3,4,6,7,12,12b-octahydro-8-Methoxy-α-(MethoxyMethylene)-indolo[2,3-a]quinolizine-2-acetic Acid Methyl Ester;16,17-Didehydro-9,17-diMethoxy-corynan-16-carboxylic Acid Methyl Ester;(16E,20beta)-16,17-Didehydro-9,17-dimethoxy-corynan-16-carboxylic acid methyl ester;MITRAGYNINE(AS)
• CAS NO: 4098-40-2
• Molecular Formula: C₂₃H₃₀N₂O₄
• Molecular Weight: 627.6
• EINECS: 200-659-6
• Product Categories: Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Neurochemicals;Alkaloids
• Mol File: 4098-40-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 92-95°C
• Boiling Point: bp5 230-240°
• Flash Point: 9℃
• Appearance: /
• Density: 1.22±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.39E-12mmHg at 25°C
• Refractive Index: 1.604
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 18.35±0.60(Predicted)
• CAS DataBase Reference: MITRAGYNINE PICRATE(CAS DataBase Reference)
• NIST Chemistry Reference: MITRAGYNINE PICRATE(4098-40-2)
• EPA Substance Registry System: MITRAGYNINE PICRATE(4098-40-2)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25-36/37/38-22
• Safety Statements: 7-16-36/37-45-26
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 1
• Hazardous Substances Data: 4098-40-2(Hazardous Substances Data)

Usage

Description

Mitragynine Picrate is an alkaloid derived from the Mitragyna speciosa Korth plant, which is known for its stimulant and opiate-like effects depending on the dosage. This amorphous compound forms a series of crystalline salts and derivatives, with the picrate form appearing as thin, orange-red needles. Mitragynine Picrate exerts a general depressant effect on plain muscle and facilitates the passage of autonomic impulses, but is ineffective against pathogenic organisms. It is a white to off-white solid.

Uses

1. Used in Pharmaceutical Industry:
Mitragynine Picrate is used as a neurochemical for its stimulant and opiate-like effects, depending on the dosage. It is currently being investigated for its potential in treating hard drug addiction.
2. Used in Research and Development:
Mitragynine Picrate is used as a research compound to study its effects on the central nervous system and its potential applications in the treatment of various conditions related to the nervous system.
3. Used in Drug Formulation:
Mitragynine Picrate, in its various salt forms, can be used in the formulation of drugs targeting the central nervous system, particularly those aimed at treating addiction and related disorders.
4. Used in Toxicological Studies:
Due to its depressant effect on plain muscle and its interaction with autonomic impulses, Mitragynine Picrate can be used in toxicological studies to understand its potential side effects and safety profile.
5. Used in Quality Control and Standardization:
The various crystalline forms of Mitragynine Picrate, such as the hydrochloride and methiodide, can be used for quality control and standardization purposes in the pharmaceutical industry to ensure the consistency and purity of the compound in drug formulations.

References

Field., J. Chern. Soc., 119,887 (1921)Raymond-Hamet, Millat., Bull. sci. pharrnacol., 40, 593 (1933)lng, Raison., J. Chern. Soc., 986 (1939)Loudon., Chern. Soc. Spec. Publ., 3, 12 (1955)Hendrickson., Chern. & Ind., 713 (1961)Joshi, Raymond-Hamet, Taylor., ibid, 573 (1963)Pharmacology: Grewal., J. Pharrn. expo Ther., 46,251 (1932)

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

• 918430-83-8 C₂₅H₃₄N₂O₆ 
• 951327-94-9 (2R,3S,12bS)-tert-butyl 3-ethyl-8-methoxy-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7-hexahydroindolo[2,3-a]quinolizine-12(12bH)-carboxylate 
• 107-31-3 Methyl formate 
• 149-73-5 trimethyl orthoformate 
• 90734-97-7 4-methoxyindole-3-carboxaldehyde 
• 83788-92-5 (E)-4-methoxy-3-(2-nitrovinyl)-1H-indole 
• 3610-35-3 4-methoxytryptamine 
• 285983-16-6 N-(2-(4-methoxy-1H-indol-3-yl)ethyl)formamide 
• 51756-08-2 methyl 2-ethyl-3-oxobutanoate 
• 210359-35-6 2-(2-methyl-1,3-dioxolan-2-yl)butan-1-ol 
• 99115-96-5 3-ethyl-4-hydroxy-2-butanone 
• 4359-77-7 3-ethyl-3-buten-2-one 
• 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 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 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 
• 174418-82-7 Mitragynine 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.