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

This alkaloid has been isolated from Mitragyna speciosa Korth, and is amorphous although it yields a series of crystalline salts and derivatives. The hydrochloride crystallizes as colourless leaflets from EtOH-Et20 with m.p. 243°C; the picrate forms thin, orange-red needles, m.p. 223-4°C and the methiodide is a pale yellow powder which, although amorphous, has a sharp melting point of 21 1. 5°C. The alkaloid also forms compounds with acetic acid, m.p. 142°C, decomposing at 175-6°, and with trichloroacetic acid, m.p. 157°C.Mitragynine exerts a general depressant effect on plain muscle and facilitates the passage of autonomic impulses. It is, however, ineffective against pathogenic organisms.

Chemical Properties

White to Off-White Solid

Uses

Different sources of media describe the Uses of 4098-40-2 differently. You can refer to the following data:
1. Mitragynine is a neurochemical, having both stimulant and opiate-like effects depending on the dosage. Currently, Mitragynine is being investigated for its ability to treat hard drug addiction.
2. A neurochemical, having both stimulant and opiate-like effects depending on the dosage. Currently, Mitragynin is being investigated for its ability to treat hard drug addiction.

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

• 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 
• 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 

Downstream Products

• 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.