Identification of mitragynine and O-desmethyltramadol in Kratom and legal high products sold online

Theresa M. Scott1,2,3, Jillian K. Yeakel1,2, Barry K. Logan1,2

1Center for Forensic Science Research and Education, Fredric Rieders Family Renaissance Foundation, Willow Grove, PA, USA, 2 Department of Chemistry, Arcadia University, Glenside, USA, 3 Michigan State Police, Northville Laboratory, Northville, MI, US

The article Identification of mitragynine and O-desmethyltramadol in Kratom and legal high products sold online, appears in the Drug Testing and Analysis Journal(Drug Testing and Analysis, 6, pages 959–963, doi: 10.1002/dta.1673). Abstract is included below.

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ABSTRACT: Kratom, or Mitragyna speciosa, is a Southeast Asian plant whose leaves have recently become available for purchase over the Internet and in retail shops as a so-called legal high, i.e. a mindaltering drug that is not scheduled or controlled. The leaves contain the alkaloid mitragynine which has been documented to have dose-dependent stimulant and opioid-like effects. Kratom is a tree indigenous to Southeast Asian countries[1] where traditionally the leaves are chewed by agricultural workers to increase work output and offset fatigue. Its use as a substitute for opium, a cure for fever, a treatment for opiate withdrawal, or to treat wounds was first documented several decades ago.[2,3]

Availability over the Internet and in retail shops reveals an increasing awareness of the potential for recreational use of this drug.[4] Many forms are available for purchase including fresh and dried leaves, powdered leaves, liquid extract, coloured ‘cake’ and small Kratom plants. Many websites offer its purchase as a new ‘remedy and tonic’, however, some do state the product is not intended for human consumption. When product reviews are read and forums are assessed, it is evident that individuals are ingesting these products to obtain euphoria. The most popular consumption method is to infuse the powder or leaves in hot water and consume it as a tea, although other ways of ingestion are also utilized, such as chewing leaves (as was done traditionally), smoking the product like marijuana,[3,5] or making an extract for ingestion. 

The most prominent alkaloids in the plant are 7-hydroxymitragynine which has been shown to be the most potent alkaloid; and mitragynine which is the most prevalent alkaloid in Kratom (Figure 1).[6] These alkaloids and other related compounds (paynanthine and specigynine) are believed to be unique to Kratom.[2] Reportedly, the effects of the plant are dose dependent with stimulant, or coca-like effects at lower doses, and opioid, or morphine-like effects at higher doses.[2,3,6] According to the World Drug Report 2013 and the European Monitoring Centre for Drugs and Drug Addiction, the increase in the recreational use of these products has resulted in a controlled status in many countries including Malaysia, Australia, Myanmar, Ireland, and Thailand.[7–9] In Ireland, mitragynine has been regulated as a controlled drug under the Misuse of Drugs Act of 1977.[10] Due to the opioid effects, the Australian government has placed mitragynine and Mitragyna speciosa on the Schedule 9 substance list, designating these substances prohibited as of 2005.[11] Kratom is not currently scheduled or controlled federally in the United States.[1] 

Fatalities have been reported where mitragynine has been found in combination with other substances. A few such fatalities involved an accidental intoxication with mitragynine and O-desmethyltramadol from a product called ‘Krypton’.[12,13] Tramadol is a synthetic opioid with agonist activity at the opiate receptors. Clinically, tramadol is prescribed due to its equal potency with codeine, and it is believed to have less respiratory depressionmaking it a safer alternative.[14] O-desmethyltramadol itself is not sold as a prescription treatment or over the counter. O-desmethyltamadol is the major metabolite of tramadol, is pharmacologically active and is believed to have 2–4 times the analgesic efficacy of the parent compound.[15] Mitragynine and O-desmethyltramadol have been found in combination in the urine of opiate users following the use of ‘Krypton’.[16,17] The presence of this major metabolite without N-desmethyltramadol, another metabolite, suggests users ingested O-desmethyltramadol.[15] 

We report the application of a method for screening, confirming and quantifying the alkaloids contained in Kratom that meets the Scientific Working Group for the Analysis of Seized Drugs (SWGDRUG) standards for the classification of controlled substances. We also evaluated the reactivity of these products in the commonly used Duquenois Levine test used for presumptive identification of marijuana, and compared the morphological characteristics of the plant to those of marijuana.

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