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Mitragynine and 7-hydroxymitragynine

Kratom’s Most Famous Alkaloids Side-by-side

For those looking for pain relief, relaxation, or energy, the alkaloids, mitragynine and 7-hydroxymitragynine, are usually the most important elements of the mitragyna speciosa plant. The first is present in much higher concentrations than the second – an average of 66% of total alkaloid content versus less than 2%, respectively. That said, the 7-hydroxy version is about 46 times stronger than the other and up to 13 times more potent than morphine by weight.

Here’s where it gets a little more complex. If you remember anything from chemistry class, you may recall that polarity influences the ability of molecules to pass through lipids. The hydroxy group present in 7-OH-mitra makes it more polar than its cousin. High polarity means greater difficulty in crossing the blood-brain barrier.Mitragynine And 7-Hydroxymitragynine Compared

The blood-brain barrier is a natural protection mechanism built into the capillaries inside the brain and designed to keep things like toxins and pathogens out while allowing beneficial substances in, though its accuracy in judgment is not perfect. The lower relative polarity of mitragynine makes it able to cross the blood-brain barrier at a rate around 10 times higher than that of 7-hydroxymitragynine, which is compounded by the former’s superior uptake by the brain.

A 2019 study found that mitragynine was actually more effective than the 7-OH version when consumed orally. That said, the study also found that mitragynine exhibits its analgesic actions as a result of undergoing conversion to 7-hydroxymitragynine. Once the substance is ingested, the body’s P450 enzymes effectively oxidize one into the other at a rate that would explain kratom’s activity at the opioid receptor.

Side note – this is actually a microcosm of what happens when red kratom is made. After naturally green leaves are dried they are set out in the sun to cure for even longer, which speeds up the oxidation process. The color red is a result of oxidation and can be indicative of greater 7-OH-mitragynine content.

What Animal Studies Have Shown Us

There are unfortunately very few studies containing information on kratom consumption by humans. One study used kratom tea in relatively low dosage, so it can not be used to draw comparisons to animal studies that used isolated alkaloids. However, there has been research performed using dogs in order to observe kratom’s effects across species.

The first kratom dog study was carried out in 2020 by Dr. Christopher McCurdy and his team at the University of Florida. The goal was to observe the pharmacokinetics and safety of kratom in nine female beagles. One of the reasons for this choice was that dogs are the closest to humans when it comes to some liver enzymes that metabolize kratom into its components.

The study found that mitragynine’s effects actually kicked in at around 30 inutes, which is about 20 minutes faster than had been reported in rat studies. This is interesting because 7-hydroxymitragynine reached its peak plasma concentrations at around an hour, which could help explain why some people feel kratom come on in waves.

In humans, peak plasma concentration of the former was once observed to occur at around 49 minutes from consumption of kratom tea. The team estimated that there was about a 23% conversion rate of mitragynine into 7-hydroxymitragynine in the beagles.

Keep in mind there was no direct 7-hydroxymitragynine given to the dogs in this study. All of the 7-OH that was present was there because the dogs bodies metabolized it from mitragynine. These effects were much more pronounced in dogs given mitragynine orally compared to the four dogs that were given it intraveneously due to enzymes present within the liver being responsible for the conversion.

Mitragynine also showed an oral bioavailability of 69.6%, which is fairly impressive given that morphine’s and hydrocodone’s are about 24% and 25%, respectively. As far as drawing comparisons between the two alkaloids, it was determined that 7-hydroxymitragynine had a 22.5 times higher binding affinity at opioid receptors.

Worth noting is blood panel work pre- and post-dosage was not significantly different. Again, this study was done with dogs and not humans. However, dogs are now the second species (third if you count the single human trial) that have shown positive responses with no adverse reactions. Rat studies have found mitragynine to exhibit little to no abuse potential.

In April of 2021, another beagle study by Dr. McCurdy was published in the European Journal of Drug Metabolism and Pharmacokinetics. This one analyzed the pharmacokinetics of oral 7-hydroxymitragynine consumption.

The dogs were closely monitored throughout the study with an eye on things like complete blood count (CBC), serum biochemical panels, and vital signs. They were also looking for any changes in food and water consumption, consciousness, and disposition.

There were no noticeable differences in behavior following administration of 7-hydroxymitragynine and no adverse events were observed. There were also no clinically significant changes in vital signs and CBC and hematological profiles were right in line with pre-trial results.

Unlike the first beagle study, peak plasma concentrations of 7-OH in this one were documented at about 10 minutes or so following the dose. One factor worth noting is that the group added time points of 5, 15, and 30 minutes to this study. Therefore, the other study could have yielded the same results if measurements were taken at the same times.

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Mitragynine And 7-Hydroxymitragynine Mitragynine

Mitragynine And 7-Hydroxymitragynine Mitragynine

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