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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.
Highlights
Mitragyna speciosa is an ethnomedicinal tree native to Malaysia, where it is named “Biak” or “Ketum”
We find it is important to determine the physicochemical properties of mitragynine, even before one attempts to establish the metabolic properties or placing effort towards designing a more appropriate dosage form that mitigates the problem associated with mitragynine’s poor oral absorption
The wavelength of the maximum difference between ionized and neutral species of mitragynine in the corresponding UV spectrum was found to be at 248 nm
Summary
Mitragyna speciosa is an ethnomedicinal tree native to Malaysia, where it is named “Biak” or “Ketum”. It has traditionally been consumed as a leaves decoction for its stimulant effects to counter fatigue. Malaysia that border Thailand, the consumption of ketum as a decoction has been popular [4]. Studies at these sites reported that ketum is widely sold as a decoction and regularly consumed by drug users to manage opiate withdrawal symptoms. A recent field study, suggests that ketum has abuse liability and can itself cause withdrawal symptoms following discontinuation after extended use [5]. Over the past decade there has been a growing interest in ketum usage outside this region as evidenced by the number of advertisements for its sale on the Internet [7]
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