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Mitragyna speciosa

Mitragyna speciosa (Kratom), (กระท่อม in Thai) is a large tree native to Thailand and Malaysia, growing to 50-100 feet (16-33m) in height. It is botanically related to the Corynanthe, Cinchona and Uncaria genii and shares some similar biochemistry. Other species in the Mitragyna genus are used medicinally in Africa.

Kratom is a well established psychoactive drug in its native region, and there is some increasing use elsewhere in the world. The leaves are usually made into a tea, although they are sometimes also chewed or extracted into water and then evaporated into a tar that can be swallowed. Kratom is not often smoked, although this method does provide some effect.

Over 25 alkaloids have been isolated from kratom including mitragynine, once thought to be the primary active as it is the most abundant alkaloid in the plant, and 7-hydroxymitragynine, which is currently the most likely candidate for the primary active chemical in the plant. Although structurally related to yohimbine and tryptamines, its pharmacology is quite different and it seems to act in some ways similarly to opiates, although it seems to also have some stimulant properties similar to yohimbine. Kratom also contains alkaloids found in uña de gato (Uncaria tomentosa) which are powerful immune system enhancers and blood pressure decreasers, as well as epicatechin, a powerful antioxidant found in dark chocolate and closely related to the ECGC that gives green tea its beneficial effects.

Most of the identified alkaloids are yohimbe-type indoles and oxindoles. The most abundant alkaloids consist of three indoles and two oxindoles. The three indoles are mitragynine, paynanthine, and speciogynine - the first two of which appear to be unique to this species. The two oxindoles are mitraphylline and speciofoline. Other alkaloids present include other indoles and oxindoles such as ajmalicine, akuammigine, corynanthedine, mitraversine, rhynchophylline, speciociliatine (also unique to kratom) and stipulatine. Working with Malay plants, Houghton and Said found new types of indole alkaloids (mitragynaline, corynantheidaline, mitragynalinic acid, and corynantheidalinic acid), in very young leaves. Those alkaloids were reported as having an unusual skeleton, having a carbon function at the C14 position (compared with previously known monoterpenoid indoles), but Takayama et al. later revised the structure of mitragynaline and corynantheidaline, showing that there was no substitution on the 14 position. Other active chemicals in kratom include raubasine (best known from Rauwolfia serpentina) and some yohimbe alkakoids such as corynantheidine.

Kratom has many potential medicinal uses, including as a safer and cheaper replacement for methadone, and as a source of chemicals with a wide range of beneficial activities.

Mitragynine (9-methoxy-corynantheidine) was first isolated in 1907 by David Hooper, a process repeated in 1921 by E. J. Field, who gave the alkaloid its name. Its structure was first fully determined in 1964 by D. Zacharias, R. Rosenstein and E. Jeffrey. It was not until 1995 that H. Takayama et al. at Chiba University were able to synthetically produce mitragynine. It is structurally related to both the yohimbe alkaloids and voacangine. It is more distantly related to tryptamine-based psychedelic drugs such as psilocybin, ibogaine or LSD. Mitragynine has the molecular formula C23H30N2O4 and a molecular weight of 398.49. Physically the freebase is a white, amorphous powder with a melting point of 102-106°C and a boiling point (bp5) of 230-240°C. It is soluble in alcohol, chloroform and acetic acid. The hydrochloride salt has a melting point of 243°C. It appears that it may be a fairly stable compound, as a mitragynine ethane disulphonate reference sample tested after fourteen years by TLC produced results not substantially different from fresh mitragynine picrate.

Alkaloid content between plants varies from place to place and at different times, leading Shellard et al. in the 1970s to conclude that there may be different geographical variants within the species. Within each location, there is a quantitative variation in alkaloid content from month to month as well. The alkaloid content of the leaves of Mitragyna speciosa has been reported as 0.5% to 1.5% in dried leaf. An average leaf weighs about 1.7 grams fresh or 0.43 grams dried (~25% of original weight.)

Takayama et al. found that Thai and Malay kratom had in common the alkaloids mitragynine, speciogynine, speciociliatine, paynantheine and 7-hydroxymitragynine. In both samples, mitragynine was the most abundant alkaloid, but in the Thai kratom it made up 66% of the total alkaloid content, while it made up only 12% of the alkaloids from the Malay sample. The Malay sample had mitragynaline and pinoresinol as major components, as well as mitralactonal, mitrasulgynine and 3,4,5,6-tetradehydromitragynine.

Beginning in the late 1990s, a group of researchers based out of Chiba University in Japan and Chulalongkorn University in Thailand began researching natural and synthetic analogues of mitragynine in search of new drugs with potential medicinal use. These studies have led to discoveries which have turned much of what was believed about kratom on its head. Results of a structure-activity relationship study published in 2002 helped to clarify the essential structural moieties in the Corynanthe type indole alkaloids required for opioid agonistic activity. Two oxidative derivatives of mitragynine, mitragynine pseudoindoxyl and 7-hydroxymitragynine, have been of particular interest.

More important is the research on 7-hydroxymitragynine (or mitragynine hydroxyindolenine), which is a naturally occurring minor alkaloid (around 2% of total alkaloids) first mentioned in a paper published in 1994. In a series of papers beginning in 2001, it has also been shown to be highly selective for mu receptors and is more potent by weight than morphine. Eventually, it occurred to the researchers that given the low potency of mitragynine, even though it is the most abundant alkaloid in the plant it can not account for the effects of kratom. Bioassays indicated that mitragynine was a much weaker anti-nociceptive than kratom extracts. Starting with crude extracts of kratom and moving then to five isolated alkaloids, it was found that 7-hydroxymitragynine is the most likely candidate for the chief agent of kratom's activity. It is thirty to forty-six times more potent than mitragynine and seventeen times more potent than morphine by weight. Antagonism by naloxone was used to confirm opioid-like activity of this alkaloid. Given that nearly all the chemical studies of kratom have been done on the assumption that mitragynine was the most important alkaloid, and that nearly all pharmacological research prior to the late 1990s was done on mitragynine or crude plant material, this discovery likely means that much of what is believed about kratom will need to be revised.

Kratom's pharmacology shares some elements of the activity of other substances including opiates and yohimbine. The comparison to opiates is sometimes emphasized by persons and businesses who are selling it, though this is frequently exaggerated. A good analogy might be comparing kava to benzodiazepines. For example, the analgesic and sedative activity of kratom is much lower than with narcotics. Kratom also does not produce such extreme constipation as opiates. Kratom also has a yohimbe-like stimulant activity, and uncaria-like immunostimulant activity. Its effects are reported to be relatively short-lived, typically fading after two to four hours or less.

Kratom contains many active alkaloidal chemicals. These include:
Ajmalicine (Raubasine), a cerebrocirculant, antiaggregant, anti-adrenergic (at alpha-1), sedative, anticonvulsant, smooth muscle relaxer; Corynantheidine, an opioid antagonist; Corynoxeine, a calcium channel blocker; Corynoxine A and B, Dopamine mediating anti-locomotives; (-)-Epicatechin, an antioxidant, antiaggregant, antibacterial, antidiabetic, antihepatitic, anti-inflammatory, anti-leukemic, antimutagenic, antiperoxidant, antiviral, cancer preventative, alpha-amylase inhibitor; 9-Hydroxycorynantheidine, a partial opioid agonist; 7-Hydroxymitragynine, an analgesic, antitussive, antidiarrheal, primary psychoactive in kratom; Isomitraphylline, an immunostimulant, anti-leukemic; Isopteropodine, an immunostimulant; Mitragynine, an analgesic, antitussive, antidiarrheal, adrenergic, antimalarial, possible psychedelic (5-HT2A) antagonist; Mitraphylline, a vasodilator, antihypertensive, muscle relaxer, diuretic, anti-amnesic, possible immunostimulant; Paynantheine, a smooth muscle relaxer; Rhynchophylline, a vasodilator, antihypertensive, calcium channel blocker, antiaggregant, anti-inflammatory, antipyretic, anti-arrhythmic, antithelmintic; Speciociliatine, a weak opioid agonist; Speciogynine, a smooth muscle relaxer; Speciophylline, An anti-leukemic; and Tetrahydroalstonine, a hypoglycemic, anti-adrenergic (at alpha-2).

The Kratom User's Guide

Kratom is classified as Narcotic Level 5 in Thailand, but still can be bought at markets in more rural towns. It is legal in all other countries besides Australia, Cambodia, Malaysia, and Myanmar. Thailand is rumored to be considering altering its legal status in light of recent discoveries of its medicinal uses in treating drug addiction. Similar research is also underway in Malaysia. Kratom is currently legal everywhere in the United States (The recently passed bill in Louisiana banning several entheobotanicals does not mention and/or include Kratom).

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“Whereas wine disorders the mental faculties, opium introduces amongst them
the most exquisite order, legislation and harmony. Wine robs a man of self-possession; opium greatly invigorates it.”
-Thomas De Quincey

“It is not opium which makes me work but its absence, and in order for me to feel its absence it must from time to time be present.”
-Antonin Artaud

“Everything one does in life, even love, occurs in an express train racing toward death. To smoke opium is to get out of the train while it is still moving. It is to concern oneself with something other than life or death.”
-Jean Cocteau

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