Kratom

What is Known About the Chemical Properties of the Mitragynine Alkaloid

The Mitragyna speciosa (kratom) plant has been used for more than 200 years for its natural analgesic and anxiolytic qualities. Its effects are attributed to the active alkaloid content contained within the plant’s leaves.

Mitragynine is an indole-based opioid-receptor agonist which is the plant’s most abundant active alkaloid and a biomarker for Mitragyna speciosa toxicity. In small concentrations, Mitragynine and kratom’s other alkaloid—7-hydroxymitragynine—can yield stimulating, euphoric and energizing effects.

Today, we’ll take a closer look at the chemistry of Mitragynine, from its clinical pharmacology to its toxicology. While there is very little known about these aspects of Mitragynine and its origins, we’ll do our best to fill in the gaps left by other kratom-related websites.

Let’s jump into it!

MITRAGYNINE’S STRUCTURE

C23H30N2O4 is the formula for Mitragynine, an indole alkaloid whose chemical structure was first fully elucidated in 1964. The chemical abstract name of Mitragynine is (aE,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.

The molecular weight of Mitragynine is 398.503 g/mol. The chemistry of Mitragynine is tricky because the FDA has ruled that there is inconclusive scientific evidence of kratom and its alkaloids. Of particular interest to the FDA and the DEA (Drug Enforcement Agency) are the active kratom alkaloids, Mitragynine and 7-hydroxymitragynine, both of which they consider to be dangerous substances.

This is what Mitragynine’s chemical structure looks like.

Mitragynine is insoluble in water, although it is soluble in organic solvents, such as alcohol, chloroform or diethyl ether. It distills at 230 degrees Celsius at 5mmHg. It forms amorphous crystals which melt at 102 degrees Celsius.

PHARMACOLOGY OF MITRAGYNINE

In a study employing a UV spectrophotomer approach and HPLC-UV method, the physiochemical properties of Mitragynine were explored. Said study found that this lipophilic (read: capable of combining with or dissolving in lipids or fats) alkaloid is acid labile (liable to be altered).

Its inadequate water solubility and hydrophobicity are believed to be responsible for the varied pharmacological responses recorded in related studies. To put it in laymen’s terms, this poor solubility means that Mitragynine may have weak or strong effects, depending upon a number of variables, including the physiological makeup and predispositions of the test subject.

The pharmakinetics (movement of drugs within the body) of Mitragynine are still unclear, but one study relying on a liquid chromatography-tandem mass spectrometry method found that Mitragynine demonstrated linearity in humans and was consistent with an oral two-compartment model with a terminal half-life of approximately one day.

This study of 10 male test subjects suggested that it could be developed as an analgesic drug in the future, although the medical establishment at large has refuted such claims ever since.

In a piece entitled Observations on the Pharmacology of Mitragynine by Khem Singh Grewal from the Pharmacological Laboratory at the University of Cambridge, Grewal notes the potential effects of Mitragynine abuse, writing, “Some claim that the addicts are thin, with distended stomachs, unhealthy complexions, dark lips, and dry skin. The main symptoms of acute overdosage are vomiting and vertigo. Numbness, muscular twitchings, and certain indefinite cardiac symptoms have been reported.”

Grewal’s journal entry also suggested that Mitragynine contains three methoxy-groups and an ester grouping. In an ester grouping, the carbon is doubly bonded to the oxygen and single bonded to the OR group which is called the alkoxy carbonyl.

Mitragynine is said to kill paramoecia at 1: 10,000 dilution with increased movement typical prior to demise.

NEUROBIOLOGY OF MITRAGYNINE

Some evidence has pointed to Mitragynine having adverse effects on cognition, although many have also claimed that kratom is cognitive enhancer. Some have used kratom for cognitive disorders, but there is no concrete proof that it promotes brain health.

The alkaloid’s anti-inflammatory properties may be behind the theory that Mitragynine could have positive neurological effects, but there is insufficient scientific evidence at this time.

CARDIOTOXICITY OF MITRAGYNINE

This bioactive compound is was studied for its potential cardiotoxicity. Findings supported the notion that Mitragynine could possibly potentiate Torsade de Pointes via inhibition of lKr in human cardiomyocytes. Torsades de pointes is a specific form of polymorphic ventricular tachycardia.

Fatal incidents involving Mitragynine have been associated with cardiac arrest. Kratom and its alkaloids have a sympathomimetic effect which can affect one’s blood pressure. Hypertension is not uncommon among kratom users with preexisting heart conditions or a history of high BP.

THE PSYCHOACTIVITY OF MITRAGYNINE

Kratom is famous for its psychoactive effects which have made it popular as an underground recreational substance. The plant’s euphoric qualities owe to this alkaloid and its psychoactive properties.

Few scientific studies have explored this aspect of the Mitragyna speciosa plant, which is odd considering that many kratom vendors sell kratom as a form of “incense” for its psychoactive effects.

MITRAGYNINE ADDICTION & WITHDRAWAL

In animal models, Mitragyna speciosa has been found to be potentially addictive when Mitragynine and its sister alkaloid, 7-hydroxymitragynine, were administered for 5 days straight.

The withdrawal symptoms from Mitragyna speciosa are similar to those of opioids in that the user may experience cramps, muscle spasms, sweating, joint pain, sleeplessness, restless legs, nausea, dilated pupils, runny nose, fever, anxiety, irritability, loss of appetite, vomiting, diarrhea or heart palpitations.

Withdrawal symptoms tend to last for 7-10 days with most acute effects subsiding within the first 2-4 days.

CLOSING THOUGHTS

Whether you are a longtime kratom advocate or someone just learning about M. speciosa, it is clear that Mitragynine is the most important component of kratom as it is the most abundant alkaloid within the kratom leaves.

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