For some #PenAndInkPoison today I want to talk about thebaine, mentioned briefly yesterday when discussing laudanosine and papaverine. Morphine gets all the glory as an opium poppy alkaloid, but I'd argue that thebaine is much, much more important.
Thebaine is not used therapeutically but is used commercially in the synthesis of some of the most important opioids we have on the market today. In anywhere from 2 to 8 steps you can produce all of the opioids shown below - there are more, but these are the important ones.
On the right, we have the opioid agonists oxycodone, oxymorphone, hydrocodone, and hydromorphone. Hydrocodone is the most frequently prescribed opioid analgesic (pain reliever) in the U.S. We all know about oxycodone (Oxycontin). And hydromorphone is used a ton in hospitals.
Opioids are vital for treating pain, both acute and chronic. It's a touchy subject, but I do think they are prescribed far too frequently and for too long, which can lead to dependence, misuse, and overdoses. Thankfully, thebaine gives us some tools to counter these effects.
Thebaine is also used in the synthesis of naloxone, an opioid antagonist and life-saving wonderdrug that reverses opioid overdoses. Since making naloxone available to the public in North Carolina, it has saved over 15,000 lives. Factor in EMS and ED use, it's saving lives.
Thebaine is also used in the synthesis of buprenorphine, a partial agonist for opioid use disorder. It keeps withdrawal symptoms at bay without giving the euphoria of opioids like fentanyl. Even though it is misused (I see it a lot), it is a vital tool in combating dependence.
To make all these drugs we obviously need a lot of thebaine. Where do we get it from? Opium poppy (Papaver somniferum). The pods are dried - what we call poppy straw - the seeds removed, and then the alkaloids, like thebaine and morphine, are extracted out. It's big business.
tl;dr
And the most important part...the pen and ink!
Pen: TWSBI ECO (F) in transparent orange.
Ink: Robert Oster Orange Rumble
And if you missed yesterday's post on laudanosine and papaverine - also from opium poppy - have no fear, you can find it here:
p.s. For more on the opium poppy used to isolate thebaine - the precursor to all those useful opioids mentioned above - see this. Most commercial opium poppy, bred to produce high concentrations of thebaine, is grown in Tasmania. It's worth the read. psmag.com/ideas/opioids-…

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More from @NaturesPoisons

Mar 3
It's Thursday! I hate Thursdays, it's a cruel reminder that it's not yet Friday. To help us feel better, let's look at how the world of nature's poisons can intersect with postmortem forensic toxicology. I present to you LAUDANSOSINE and PAPAVERINE.
Laudanosine and papaverine are minor alkaloids found in the opium poppy (Papaver somniferum), but they don't get near the attention of the heavy-hitter opiate morphine, which is made (rather simply) into heroin. Other alkaloids found in opium poppy are codeine and thebaine.
Laudanosine sounds very similar to laudanum, the opium tincture that was common in the 1800s. It was ~10% opium alkaloids, and when drunk, had the same effects of opiates/opioids today, like euphoria, but also the same side effects, namely respiratory depression and dependence.
Read 14 tweets
Mar 2
Do you need a break? Are y'all up for a quick Pen & Ink Poison? This magnificent beast is Brevetoxin-1. I love all the polycyclic ethers and the fact that it has 5, 6, 7, 8, and 9-membered rings. But as lovely as she is, she's quite harmful, both physically and economically. Image
There are about a dozen structurally similar brevetoxins that are produced by the dinoflagellate (a.k.a. algae) Karenia brevis. This algae is responsible for the "red tides" along the Gulf Coast in states like Florida.
"Red tides" are harmful algal blooms (HABs), and the name is a bit of a misnomer because not all infected water is "red" and not associated with tides. But I digress. HABs due to Karenia brevis will shut down beaches and cause people to flee. Image
Read 12 tweets
Mar 1
It's ToxTuesday. I know we could use a little breather from *all this*, so let's take a look at a scary toxin, ORELLANINE, and admire another pretty @twsbi pen. (If you want to sponsor me, TWSBI, hit me up! 😅)
Orellanine is a mycotoxin, a toxin produced by fungi. Specifically, it is found in Cortinarius orellanus and Cortinarius rubellus, commonly known as "fools webcap" and "deadly webcap" mushrooms.
Pro tip: Don't eat things with "deadly" in their name.
Ingestion of these mushrooms is a horrible idea because orellanine is nephrotoxic - it destroys your kidneys. Absolutely ravages them. The exact mechanism of toxicity is unclear, but it could be due to interfering with redox reactions in the cell and increasing oxidative stress.
Read 12 tweets
Feb 22
It's ToxTuesday and we're going to talk about nicotine. I know what you're thinking, "nicotine poisoning isn't sexy," but I'm here to change your mind. So I present to you Green Tobacco Sickness. Image
North Carolina, and Durham, was founded on tobacco. There was huge money in tobacco, but even though the industry is in decline, it's still important to NC with revenue of ~$1B/yr. As an aside, the Durham Bulls were originally named the Tobacconists in 1902 (cc @stephaniekays). Image
Downtown Durham is full of abandoned tobacco warehouses, in the process of being turned into trendy overpriced "urban lofts." But drive five miles north, and you'll still see small tobacco farms. Image
Read 12 tweets
Nov 22, 2021
Happy Monday!
I'm often asked what the "best" poison to die from is - i.e. quick or painless. Well, the other day a colleague asked me what I thought the "worst" poison was. There's no right answer, but I almost always go with colchicine. A 🧵
Colchicine is a prescription drug used to treat gout but it also has the most lovely natural sources, like the autumn crocus and the flame lily 😍. I'm sure you can figure out which is which.
As a drug, colchicine has a very narrow therapeutic window - meaning the difference in the amount of drug that does good, to that which harms, is small. This means the risk of toxicity is high.
Read 15 tweets
Oct 22, 2021
Jake died last May, presumably from taking a Xanax mimic containing fentanyl, the family released yesterday. This tragic death is sure to shed light on the growing problem of "fake pills," so here's everything you need to know about them. A 🧵. si.com/college/2021/1…
"Fake pills" have been around for a long time, but they received national attention in late 2015, when several people in SanFransisco died after taking Xanax bars purchased off the street. They were not alprazolam, but contained fentanyl, instead. cbsnews.com/news/fake-xana…
Much like bootleg Gucci bags, there's some terminology here regarding these knockoff pills:
Counterfeit - looks real, has the actual drug
Fake - looks real, has no drug
Mimic - Looks real, has other drugs
Read 14 tweets

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