Speciociliatine

Speciociliatine is a major alkaloid of the plant Mitragyna speciosa, commonly known as kratom. It is a stereoisomer of Mitragynine and constitutes 0.00156 - 2.9% of the dried leaf material.[2][3]

Speciociliatine
Legal status
Legal status
  • US: Unscheduled
Identifiers
  • methyl (E)-2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC23H30N2O4
Molar mass398.503 g·mol−1
3D model (JSmol)
Melting point104 °C[1]
  • CC[C@@H]1CN2CCC3=C([C@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)NC4=C3C(=CC=C4)OC
  • 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
  • Key:LELBFTMXCIIKKX-MYLQJJOTSA-N

Pharmacology

Pharmacodynamics

Speciociliatine has found to be a ligand of the mu and kappa opioid receptors, however findings are varied as to whether it functions as an agonist or a competitive antagonist at those sites.[4][5]

Pharmacokinetics

A preliminary pharmacokinetic analysis in male Sprague Dawley rats determined the elimination half-life of Speciociliatine to be 2.6 - 5 hours and the absolute bioavailability to be 20.7% (at an oral dose of 20 mg/kg).[6]

References
  1. "National Center for Biotechnology Information (2022). PubChem Compound Summary for CID 15560576, Speciociliatine".
  2. Manwill, P. K., Flores-Bocanegra, L., Khin, M., Raja, H. A., Cech, N. B., Oberlies, N. H., Todd, D. A. (2022), Kratom (Mitragyna speciosa) Validation: Quantitative Analysis of Indole and Oxindole Alkaloids Reveals Chemotypes of Plants and Products, Georg Thieme Verlag KG
  3. Sharma, A., Kamble, S. H., León, F., Chear, N. J. ‐Y., King, T. I., Berthold, E. C., Ramanathan, S., McCurdy, C. R., Avery, B. A. (2019), Simultaneous quantification of ten key Kratom alkaloids in Mitragyna speciosa leaf extracts and commercial products by ultra‐performance liquid chromatography−tandem mass spectrometry, Wiley
  4. Obeng, S., Kamble, S. H., Reeves, M. E., Restrepo, L. F., Patel, A., Behnke, M., Chear, N. J.-Y., Ramanathan, S., Sharma, A., León, F., Hiranita, T., Avery, B. A., McMahon, L. R., McCurdy, C. R. (2019), Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids, American Chemical Society (ACS)
  5. Kruegel, A. C., Gassaway, M. M., Kapoor, A., Váradi, A., Majumdar, S., Filizola, M., Javitch, J. A., Sames, D. (2016), Synthetic and Receptor Signaling Explorations of the Mitragyna Alkaloids: Mitragynine as an Atypical Molecular Framework for Opioid Receptor Modulators, American Chemical Society (ACS)
  6. Berthold, E. C., Kamble, S. H., Raju, K. S., King, T. I., Popa, R., Sharma, A., León, F., Avery, B. A., McMahon, L. R., McCurdy, C. R. (2021), Preclinical pharmacokinetic study of speciociliatine, a kratom alkaloid, in rats using an UPLC-MS/MS method, Elsevier BV
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