methyl (2E)-2-[(2S,3S,12bS)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

• ChemBase ID: 174657
• Molecular Formular: C23H30N2O4
• Molecular Mass: 398.4953
• Monoisotopic Mass: 398.22055745
• SMILES: c12c(CCN3[C@H]1C[C@@H]([C@@H](C3)CC)/C(=C\OC)/C(=O)OC)c1c([nH]2)cccc1OC
• Canonical SMILES: CO/C=C(\[C@H]1C[C@@H]2N(C[C@H]1CC)CCc1c2[nH]c2c1c(OC)ccc2)/C(=O)OC
• InChI: InChI=1S/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
• InChIKey: LELBFTMXCIIKKX-QVRQZEMUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2E)-2-[(2S,3S,12bS)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
• IUPAC Traditional name: mitragynine
• Synonyms: (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; (-)-Mitragynine; 9-Methoxy-corynantheidine; 16,17-Didehydro-9,17-dimethoxy-corynan-16-carboxylic Acid Methyl Ester; Mitragynine

Database IDs

• CAS Number: 4098-40-2
• PubChem SID: 164230567
• PubChem CID: 3034396

CALCULATED PROPERTIES

• Acid pKa: 16.670277
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.4754633
• LogD (pH = 7.4): 3.0337396
• Log P: 3.2995937
• Molar Refractivity: 112.9132 cm^3
• Polarizability: 45.03689 Å^3
• Polar Surface Area: 63.79 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White to Off-White Solid
• Melting Point: 92-95°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M373550

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.

REFERENCES

• Kikura-Hanajiri, R., et al.: For. Toxicol., 27, 67 (2009)
• Bjoernstad, K., et al.: Clin. Toxicol., 47, 566 (2009)
• Parthasarathy, S., et al.: Anal. Bioanal. Chem., 397, 2023 (2009)