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Molecules 2015, 20(3), 4915-4927; doi:10.3390/molecules20034915

Understanding the Physicochemical Properties of Mitragynine, a Principal Alkaloid of Mitragyna speciosa, for Preclinical Evaluation

1
Centre for Drug Research, Universiti Sains Malaysia, Penang 11800, Malaysia
2
School of Pharmaceutical Sciences, Universiti Sains Malaysia, Penang 11800, Malaysia
3
Advanced Medical & Dental Institute, Universiti Sains Malaysia, Bertam, Kepala Batas, Penang 13200, Malaysia
4
Institute for Research in Molecular Medicine, Universiti Sains Malaysia, Penang 11800, Malaysia
*
Author to whom correspondence should be addressed.
Academic Editor: Patricia Valentao
Received: 12 January 2015 / Accepted: 27 February 2015 / Published: 18 March 2015
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
View Full-Text   |   Download PDF [720 KB, uploaded 18 March 2015]   |  

Abstract

Varied pharmacological responses have been reported for mitragynine in the literature, but no supportive scientific explanations have been given for this. These studies have been undertaken without a sufficient understanding of the physicochemical properties of mitragynine. In this work a UV spectrophotometer approach and HPLC-UV method were employed to ascertain the physicochemical properties of mitragynine. The pKa of mitragynine measured by conventional UV (8.11 ± 0.11) was in agreement with the microplate reader determination (8.08 ± 0.04). Mitragynine is a lipophilic alkaloid, as indicated by a logP value of 1.73. Mitragynine had poor solubility in water and basic media, and conversely in acidic environments, but it is acid labile. In an in vitro dissolution the total drug release was higher for the simulated gastric fluid but was prolonged and incomplete for the simulated intestinal fluid. The hydrophobicity, poor water solubility, high variability of drug release in simulated biological fluids and acid degradable characteristics of mitragynine probably explain the large variability of its pharmacological responses reported in the literature. The determined physicochemical properties of mitragynine will provide a basis for developing a suitable formulation to further improve its solubility, stability and oral absorption for better assessment of this compound in preclinical studies. View Full-Text
Keywords: mitragynine; partition coefficient; pharmacology; pKa/pH; solubility; stability mitragynine; partition coefficient; pharmacology; pKa/pH; solubility; stability
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Ramanathan, S.; Parthasarathy, S.; Murugaiyah, V.; Magosso, E.; Tan, S.C.; Mansor, S.M. Understanding the Physicochemical Properties of Mitragynine, a Principal Alkaloid of Mitragyna speciosa, for Preclinical Evaluation. Molecules 2015, 20, 4915-4927.

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