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Tramadol discovered in African plant!

This is a dupe of this older thread. I'll reiterate the pertinent bits here.

The researchers were looking for novel plant-based painkillers, presumably by examining various traditional preparations. The root bark of N. latifolia is used traditionally as a tea for indigestion and pain and the like, so the research team seperated it by HPLC and found the portion with the most activity as a painkiller. The compound was partially blocked by naloxone and upon further analysis, the most active fraction proved to be essentially pure cis-(+/-)-tramadol free base. (Cis-(+/-)-tramadol is the common isomer of tramadol used as a painkiller).

The root bark of N.latifolia contains about 1% by mass tramadol. The extraction procedure, quoted below, is a basic extraction that produced about 1% of 95% pure tramadol.

The presence of a basic nitrogen atom in the compound structure prompted us to establish a more appropriate extraction procedure, routinely used in the extraction of naturally occurring alkaloids. For this, roots of N. latifolia (20 g of powder) were mixed with absolute ethanol (300 mL) and refluxed for 24 hrs (Soxhlet system). Ethanol was evaporated and the residue was diluted in HCl (5%) and extracted with dichloromethane. The aqueous solution was treated with a saturated aqueous solution of NaHCO3 (pH 6-7). The solution was extracted with dichloromethane, which was dried over MgSO4 and evaporated. The residue obtained was triturated with diethyl ether and filtered. The residue was collected and dried under vacuum to yield 200 mg of pure tramadol as an oily yellow liquid. This corresponded to a yield of 1%. Purity of the product obtained by this protocol was > 95%.
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The researchers also took pains to ensure the tramadol was really present in the roots, and not from contamination of the plant material or contamination during analysis. Not only did they extract several samples of root from different times and places, they also did isotopic profiling on the tramadol to verify it was made in a plant and not synthetically. (This was to help prevent the Acacia fuckaround, where a Texas lab found a whole shitload of drugs, from meth to mescaline, in Acacia spp., but the results have never been duplicated.)

There's a few curious implications this paper brings up.
  • There's other varieties of Nauclea that may contain tramadol or related compounds.
  • We could, in theory, tweak the plant to make tramadol analogues, or perhaps make enzymatically-produced tramadol. Or, poppy plants that make tramadol and morphine :)
  • As tramadol is a natural product now, it would be possible to sell OTC tramdol, wouldn't it?
 
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Morphine is a natural product of opium poppies, but it's not possible to sell OTC because it's a controlled substance under both international and most national jurisdictions.

Should be possible. But it isn't.
 
tramadol is disgusting. like honestly, i value codeine over that junk.

but i guess from a scientific perspective, pretty cool, and really random.

but to me as a junkie, whooop dee doo, we have kratom and loperamide OTC, and those are infinitely more useful than tramadol
 
RedRum OG said:
tramadol is disgusting. like honestly, i value codeine over that junk.

but i guess from a scientific perspective, pretty cool, and really random.

but to me as a junkie, whooop dee doo, we have kratom and loperamide OTC, and those are infinitely more useful than tramadol
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Good thing we have scientists to do the work instead of junkies.... ;)
 
How is loperamide "infinitely more useful" than tramadol?

Last I checked, there's a bit of a blood brain barrier issue.
 
I'm waiting for natural-source o-desmethyl-tramadol :)
 
sekio said:
Tramadol isn't a controlled drug though. (Suprising!)
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They rescheduled tramadol (IV) along with hydrocodone preperations (to sch. II I believe) recently (about 6 months ago). Might have been a state thing but it was a memo I read at work.
 
False_findings_jpeg.jpg

From the Wikipedia article on tramadol.
 
Yeah, there's been a bit of a back-and-forth since the original claim was published, but it seems pretty clear at this point that the tramadol was there due to human activity.
 
Got to admit, tramadol is a mixed bag, so to speak. The reaction depends vastly on the individual. I HATE tramadol. Its revolting. Some love it, some loathe it, doesn't seem to be much in between.
 
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