Mitragynine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Mitragynine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Mitragynine?

The molecule Mitragynine presents a molecular formula of C23H30N2O4 and its IUPAC name is methyl (E)-2-[(2S,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate.

Mitragynine is an indole-based alkaloid molecule isolated from the leaves of the kratom tree, Mitragyna speciosa. First discovered in 1907 by D. Hooper, mitragynine is structurally similar to yohimbine and other tryptamines, and acts as a partial agonist at the μ-opioid receptor and serotonin 5-HT2A receptor. It is the primary active compound in kratom, and is responsible for its analgesic and psychoactive effects..

Mitragynine has a complex pharmacology, and produces different effects at different doses. Low doses (<1 gram) of kratom tend to produce stimulant effects, whereas higher doses (>5 grams) produce sedative effects. At moderate doses (1-5 grams), kratom produces analgesic and Euphoric effects..

The exact mechanisms by which mitragynine produces its effects are not fully understood, but it is thought to work by binding to and activating the μ-opioid receptor, as well as by inhibiting the reuptake of serotonin and noradrenaline..

Mitragynine is not currently scheduled as a controlled substance in any country, and is legal to purchase and consume in most jurisdictions. However, there is a growing movement to regulate or ban kratom, as it is increasingly being used for recreational purposes and has been linked to a number of deaths..

3D structure

Cartesian coordinates

Geometry of Mitragynine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Mitragynine LELBFTMXCIIKKX-QVRQZEMUSA-N chemical compound 2D structure molecule svg
Mitragynine

 

Molecule descriptors

 
IUPAC namemethyl (E)-2-[(2S,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
InChI codeInChI=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
InChI KeyLELBFTMXCIIKKX-QVRQZEMUSA-N
SMILESCC[C@@H]1CN2CCc3c([nH]c4cccc(OC)c34)[C@@H]2C[C@@H]1/C(=C\OC)C(=O)OC

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (-)-Mitragynine
  • (.ALPHA.E,2S,3S,12.BETA.S)-3-ETHYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-8-METHOXY-.ALPHA.-(METHOXYMETHYLENE)-INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID METHYL ESTER
  • (E)-Methyl 2-((2S,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-methoxyacrylate
  • 16,17-Didehydro-9,17-dimethoxy-17,18-seco-20-alpha-yohimban-16-carboxylic acid methyl ester
  • 4098-40-2
  • 6202-22-8
  • 9-Methoxycorynantheidine
  • BDBM50474152
  • BM164595
  • C09226
  • EP479K822J
  • HSDB 7901
  • INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID, 3-ETHYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-8-METHOXY-.ALPHA.-(METHOXYMETHYLENE)-, METHYL ESTER, (.ALPHA.E,2S,3S,12BS)-
  • MITRAGYNINE
  • MITRAGYNINE PICRATE
  • Mitragynin
  • Mitragynine
  • Q414299
  • SK&F 12711
  • Skf 12711
  • methyl (2E)-2-[(2S,4S,5S)-5-ethyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate
  • methyl(e)-2-[(2s,3s,12bs)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC13473305
  • UNII-EP479K822J
  • DTXSID701032140
  • CHEMBL299031
  • CHEBI:6956
  • SCHEMBL875799
  • SCHEMBL875800

Physico-Chemical properties

IUPAC namemethyl (E)-2-[(2S,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
Molecular formulaC23H30N2O4
Molecular weight398.495
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity116.89
LogP3.8
Topological polar surface area63.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.