Mitragynine

Base Information

• Chemical Name: Mitragynine
• CAS No.: 4098-40-2
• Deprecated CAS: 1383-32-0,6202-22-8
• Molecular Formula: C₂₃H₃₀N₂O₄
• Molecular Weight: 398.502
• Hs Code.: 29339900
• European Community (EC) Number: 863-118-9
• UNII: EP479K822J
• DSSTox Substance ID: DTXSID701032140
• Nikkaji Number: J8.681I
• Wikipedia: Mitragynine
• Wikidata: Q414299
• Pharos Ligand ID: UU5H3Y6VSFQJ
• Metabolomics Workbench ID: 49638
• ChEMBL ID: CHEMBL299031
• Mol file: 4098-40-2.mol

Synonyms:16,17-didehydro-9,17-dimethoxy-17,18-seco-20-alpha-yohimban-16-carboxylic acid methyl ester;kratom alkaloids;mitragynine;mitragynine ethanedisulfonate;mitragynine monohydrochloride;mitragynine, (16E)-isomer;mitragynine, (3beta,16E)-isomer;mitragynine, (3beta,16E,20beta)-isomer;SK and F 12711;SK and F-12711;SKF 12711

Chemical Property of Mitragynine

Chemical Property:

• Vapor Pressure: 1.39E-12mmHg at 25°C
• Melting Point: 92-95oC
• Boiling Point: 560.3°Cat760mmHg
• PKA: 18.35±0.60(Predicted)
• Flash Point: 292.7°C
• PSA: 63.79000
• Density: 1.22g/cm³
• LogP: 3.76300
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 398.22055744
• Heavy Atom Count: 29
• Complexity: 624

Purity/Quality:

98%,99%, ^*data from raw suppliers

Mitragynine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• 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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CN2CCC3=C(C2CC1C(=COC)C(=O)OC)NC4=C3C(=CC=C4)OC
• Isomeric SMILES: CC[C@@H]1CN2CCC3=C([C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)NC4=C3C(=CC=C4)OC
• 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.
• Uses: 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. 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.

Technology Process of Mitragynine

There total 46 articles about Mitragynine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

C25H34N2O6 → mitragynine (4098-40-2,4697-67-0,14382-79-7,14509-92-3,6202-22-8)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In methanol; at 20 - 90 ℃; Inert atmosphere; Reflux;

Reference yield: 99.0%

(-)-dehydromitragynine (1415662-51-9,1346-36-7) → mitragynine (4098-40-2,4697-67-0,14382-79-7,14509-92-3,6202-22-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 18h;

DOI:10.1039/c2cc37023a

Reference yield: 80.0%

C25H34N2O6 (918430-83-8) → mitragynine (4098-40-2,4697-67-0,14382-79-7,14509-92-3,6202-22-8)

Guidance literature:

C₂₅H₃₄N₂O₆; With sodium cyanoborohydride; acetic acid; at 20 ℃; Inert atmosphere;

In methanol; at 90 ℃; Inert atmosphere;

upstream raw materials:

(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

C₂₅H₃₄N₂O₆

(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

Methyl formate

Downstream raw materials:

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

Mitragynine hydroxyindolenine

O-Acetylmitragynine hydroxyindolenine

Refernces

• 1、 -. "MITRAGYNINE ALKALOIDS AS OPIOID RECEPTOR MODULATORS". Page/Page column 74; 78; 79. . Retrieved 2017/10/13.
• 2、 Kerschgens, Isabel P.,Claveau, Elise,Wanner, Martin J.,Ingemann, Steen,Van Maarseveen, Jan H.,Hiemstra, Henk. "Total syntheses of mitragynine, paynantheine and speciogynine via an enantioselective thiourea-catalysed Pictet-Spengler reaction". supporting information. p. 12243 - 12245. Retrieved 2013/01/16.