Friday, December 18, 2009

On poison, fugu, pufferfish, and tetrodotoxin

An image of a porcupine fish used as a lantern at your humble scribe's abode, entitled 'Death incarnate. Or his cousin.'.Dear Gentle Reader,

You're back!

I wasn't sure you'd return.

Care for some wine?

A taste of the goodness in Borgia's cup, perhaps?

No, today there will be no drinking. We don't want to gag.

Only solid(ish) food, today.

And a tale from the field.

Monday's image was a close-up section of today's image which shows a lantern in your humble scribe and Heroine's home, made from a fish.

This fish is not the fabled fugu, the pufferfish.

This is its cousin, the porcupine fish, a blowfish.

Both fish blow or puff themselves up, but blowfish have huge, very conspicuous spines studding their body, whilst pufferfish have much smaller, more slender, delicate spines.

Both, mind you, are well-equipped, internally, with tetrodotoxin, sometimes known as TTX.

Tetrodotoxin, C
11H17N3O8, has a really fancy IUPAC name:
Image of tetrodotoxin, TTX, sourced from the Wikimedia Commons; in the public domain.Octahydro-12-(hydroxymethyl)-2-imino-5,9:7,10a-dimethano-10aH-[1,3]dioxocino[6,5-d]pyrimidine-4,7,10,11,12-pentol.

Try dropping that in conversation.

Just don't drop it in the wine. Or in the food.

Unless you want to best the Borgia's and their relatively tame cantarella, by comparison, at least.

There is no known antidote to TTX; no known cure. And the puffer fish, specifically Takifugu rubripes, the torafugu, is the second-most poisonous vertebrate on planet Earth.

What does tetrodotoxin do?

Well, it's a bit like that hemlock that Socrates drank.

TTX paralyzes you and then you drown in the fluid that accumulates in your lungs.

But, TTX does so much more than that. It shuts everything down, except that, usually, you are lucid right until the end. Although you might feel a floaty sensation and a few other tricks of the mind.

TTX is a neurotoxin which blocks sodium transport channels for your nerves--it stops your nerves from working.

People with multiple sclerosis, for example, have damaged myelin sheathes, the insulation around the electrical lines in our bodies that we call nerves.

When the myelin sheath is damaged the electrical differential across the nerve diminish and there no longer is enough of a differential to reliably push signals around the body.

So, people in later stages of multiple sclerosis find that their body stutters around like a car engine trying to start with a dead battery.

The neurotoxin TTX doesn't just diminish the electrical differential, however, it stops it.

If there is only a little bit of toxin, your body might process it before you die.

You have 24 hours to live. Live that long and you keep on living.

If not... you don't need to worry about whether you left the lights on; your's will be out.

And not much TTX is needed. Based upon the Sigma-Aldrich (a chemical supply company) Material Safety Data Sheet for TTX it can be calculated that 25 milligrams (0.000881 oz) of tetrodotoxin would be enough to kill a 75 kg (170 lb) person who consumed that much TTX orally.

If TTX was injected into you, say via a pufferfish or blowfish spine, then around half a milligram (0.00002 oz) of TTX would likely do you in.

If you're lucky. though, and survive 24 hours, then you are fine.

Some researchers think that the poison accumulates in pufferfish and blowfish due to a bacteria which they harbour. Others think that TTX is generated by the fish themselves.

An engineer would say... who cares? The fish kills.

The gourmet, however, says... I wonder what it tastes like?

Which was my reaction, years and years ago, on my first encounter, on a two week canoe trip in the Northern reaches of Saskatchewan, on seeing poisonous hemlock. The stuff that killed Socrates.

"I wonder what it tastes like?" I said as I reached out to touch the stuff that had killed Socrates.

And then I reached back to hold my head where the guide, who was in my canoe, had walloped the back of my head with his paddle. (The square root of 64....7?)

I still don't know what hemlock tastes like... nor what the square root of 64 is...

You have no idea how curious I am, too... regarding the taste...

Anyway, back to the pufferfish and to the blowfish.

Handling those fish is tricky.

Filleting one of those fish is also tricky.

Most of the poison is in the organs on the inside, especially in the liver.

One slip of the knife, into an organ, and the poison comes, with the knife, back through the flesh.

Then the eater will likely be dead.

And the chef will be out a job.

My lantern is from the body of a porcupine fish, a blowfish--the one with the bigger spines; it's easier to handle than a pufferfish.

Not only that, but there is slightly less poison in a blowfish than in a pufferfish.

What does that information tell you?

It tells you that if you are going to go to the effort to find and eat one of these fishes, make sure you eat the pufferfish. It's more dangerous and more deadly.

Go for Takifugu rubripes, the torafugu; it's the deadliest and the most expensive.

Only specially trained chefs can prepare and serve fugu in Japan. And it can be quite expensive.

Even when your humble scribe lived in Japan, he never ate it. His girlfriend at the time was against it.

But, like the hemlock, he always wanted to know what it tasted like.

When I lived in Taiwan, I went on an expedition to Penghu (澎湖群島), the archipelago of Taiwanese fishing islands far off the west coast of Northern Taiwan, and very close to Mainland China.

The Portugese called these islands the Pescadores because of the fisherman there and the Portugese found this to be a good place to revictual their ships on their way to the Spice Islands.

The Pescadores were well named; they are excellent for fish and for fishermen.

And, it turns out, for fishermens' daughters.

I found myself in the village headmaster and headfisherman's home.

His daughter had dragged me there and I quite happily went; I knew the food would be fresh.

An aside, I never learned any Taiwanese, besides "I'm full", when I lived in Taiwan.

I could understand some Mandarin, but Taiwanese was completely outside my linguistic abilities.

So, while the girl I was with spoke Mandarin, it never occurred to me that her family would not speak Mandarin.

They only spoke Taiwanese.

The father had invited me, I think, to go out onto the boat all day, that morning.

One look at the choppy waves out the window and I knew that fishing was not in the cards. This girl was great, but she was not the one, and I was not about to slam up and down on that surf.

I wanted to enjoy future dinners, not relive past ones.

Besides, this was my opportunity to hang out in the kitchen with a woman who had cooked seafood her entire life. There would be much I could learn, even if it was all delivered in rapid Taiwanese by someone who still looked astonished that a man would want to hang out in her kitchen.

So be it.

The room had concrete walls, low, squat, snug, and capable of keeping howling typhoons out when typhoons would blow over the island.

The windows were small and shuttered; the light was poor and particles of fat from the morning's cooking hung in the air as they oh-so-slowly coalesced on every surface.

The floor was concrete covered in a peeling linoleum that was curling at the edges. It would have been good for quick cleaning of fish guts with a bucket of water, once.

A small, chipped formica table was the centrepiece of the room, and a hefty round of wood was on that table.

That wood, with deep grooves from countless passes of the knife, was the cutting stump--board or block would be totally unacceptable descriptions for this chunk of tree.

At a glance you could tell where, on the surface, various cutting operations had taken place over the years which was good because direct observation was impossible.

The cooking knife, one singular knife, a fairly hefty cleaver with rust on its thick spine but a wickedly glittering cutting edge, sharpened daily, moved like the wind.

Watching this woman was watching an artisan with decades of experience and generations of learning, but I had no idea what she was doing, or even what she had just done, at any given moment. My knowledge of the knife and its purpose was Heisenbergian at best.

Her craft was one to be learned from the crib, by osmosis.

Nothing was explained; she just had a conversation with me the whole morning. Or, really, with herself.

I never had a clue what she was saying or asking. I just smiled and, eventually, had my own conversation with myself, out loud, in return.

At some point in time the girl woke up and sauntered into the room, surprised that I hadn't left with her Pa on the boat.

But, I'd seen his gaffing stick.

I knew where it was safe, although I would never say that.

Shortly afterwards, she obviously knew the rhythm of the home, her Pa came home. It hadn't been a long trip; I would have been fine. But, how was I to know?

Anyway, Pa strolled into the kitchen, with his rolling gait, and dropped a big bucket of fish, still alive and swimming, onto the table for his wife to prepare, presumably for lunch.

If I hadn't thought his daughter was 'the one' for me, before, it was also obvious that he didn't think I was 'the one', either. But, appearances had to be preserved.

I looked inside the bucket.

Baby octopi filled it.

And little pufferfish.

Pufferfish that looked a lot like Takifugu rubripes, the torafugu.


This was going to be great.

Then the preparation began.

First, the mother dipped her hands into the bucket of sea water, pulled up most of the octopi, and dropped them onto the chopping block.

Then she turned and started talking to her husband.

It sounded like she was arguing, but Chinese can sound that way.

The baby octopi, unhappy at finding themselves out of water, were squiggling to the edge of the block, then falling onto the formica table, and spreading out on a mistaken theory that she couldn't get all of them and that some of them would escape.

An aside. If you scuba dive you know that octopi are actually quite shy.

Like a family dog.

They remember you.

I've always had dogs.

I've always remembered my dogs and they've always remembered me.

And I don't eat them.

I eat octopi, but not the ones that I play with when scuba diving.

Watching the octopi kaleidescope themselves around the table was a bit like playing with them.

Except that they were fleeing for their lives.

I was trying to figure out how many I could save and release.

Then the mother turned around, picked up the knife, and decimated the class of octopi as they pirouetted away.

(If fish form schools then the more intelligent octopi must be in classes. You heard it here, first.)

Now I knew why the formica table was so pitted and gashed.

She pointed to the site of the octopi massacre and handed me a plate. I put the grey limbs of the octopi onto the plate as I surreptiously picked out a few bits of formica.

Interestingly, for those who don't live by the sea, octopi are a healthy pinky purpley colour. Until you chop a bit off of them. The second you chop a tentacle off that tentacle becomes grey. Instantly.

I tried to work out the rate of change and the mechanism by watching the main body of each octopi change to grey more slowly in contrast to the instantly grey limbs. Then I realized that the limbs were instantly 'dead' whereas the little baby bodies were dying more slowly of blood loss and oxygen deprivation.

Great. There goes the appetite.

And I can see that Pa brought extra octopi after my capacious belly display of the previous evening.


As I was doing this, I was thinking about the pufferfish. Or, rather, of the fish that looked like pufferfish.

I know that nobody handles pufferfish in Japan with their bare hands.

People use very thick, special gloves.

And this lady had just dipped her hands in amongst the startled, puffed up pufferfish to grab the octopi.


These might not be the real things.

Then, to prove a point, she started to grab pufferfish from the bucket, clean them on that formica table, and fillet them on that big uneven block. With her bare hands. Without looking.

That vorpal blade went snicker-snack. She left them dead, and, with their head, she went galumphing back.

And that lady looked at me the whole time, and carried on her conversation.

So these definitely were not 'real' pufferfish.

Shortly afterwards, her husband and both daughters came into the kitchen.

We all crowded around the table eating fresh octopi dipped in some sauce she had made earlier, and slices of raw not-real-pufferfish.

I tried desperately to follow the dynamics, figure out what was expected of me, figure out which sauce was to go where, and to keep the wandering hand of the daughter at bay as her frankly terrifying father glared at me and sharpened a fearsome fishing blade between using his chopsticks to eat the fish.

I was getting pretty apprehensive about her Pa; he was really giving me the willies.

That knife was giving me the willies, too.

Pa took very few octopi, indicating that there were more for me and that, as the honoured guest, I should be eating up. Or was I trying to let him know that this was not good enough for me?

I don't speak Taiwanese, but some things you just figure out.


Come here boy.




Puppy octopi.

...This was really starting to get to me.

Throughout all this I kept eating the faux pufferfish, trying to make sense of everything going on around me.

I was feeling a bit light-headed from everything going on, not quite dizzy, but almost floaty.

And then I poked the back of my mouth with my chopsticks--hard.

Which is something that you really shouldn't do.

It would be like jabbing the tines of your fork into the back of your throat; bad form.

What type of barbarian can't even use eating utensils?

And then I realized that I couldn't feel my lips.

Or my mouth.

Or my tongue.

Or my neck or shoulders.

And there was a fast, slick, creeping sensation, like a swift slug sliding up towards my eyes, and wiping out my ability to sense anything or feel anything.

That's when I realized that the pufferfish was real.

I also realized that I had a chunk of fish somewhere right beside my trachea, although I couldn't feel a thing.

Like a bit of a madman I forced my lungs to exhale and sent a chunk of fish flying.

Onto Pa.

Who was in mid-stroke of sharpening that blade.

And I gesticulated, as best I could, as my anxiety rose while that invisible slug stole all sensations from me.


Well, obviously I survived.

And my paranoia and apprehension, it turns out, were side symptoms of the early stages of pufferfish/TTX poisoning.

And the whole family, apparently, all liked me a lot, especially how attentive I seemed to be to everything, even if our ability to communicate was nil, and even if I was a wimp for sitting in the kitchen rather than going onto the boat.

As to what fugu tastes like? That special Takifugu rubripes, the torafugu?

I haven't a clue.

I didn't think it was real fugu--I was trying to figure out what was going on.

And my tongue and nasal cavity were the first things to be affected.

...Next time...


And the music for today is...

Monday, December 14, 2009

On poison, naturally

Image of something angular and round, lit up by night titled 'What is this?'.Dear Gentle Reader,

After Friday, I kept thinking about poison. And food.

I thought about strychnine, for example.

Strychnine brought me back to Dr. Thomas Neil Cream (1850-1892), the Lambeth Poisoner, who gave strychnine to young woman, from the USA to England, who aroused him.

When young ladies came to his practice dressed inappropriately, according to his private determination (read arousal), he would retaliate (?) by giving them candy--strychnine tablets.

The young women would be dead by the next morning.

Those 'candies' were taken by the girls themselves, but at least they didn't know what they were popping into their mouths.

I say that because the next person and poison I thought of was poor Socrates (469 BC - 399 BC) who was required by the State to willingly drink hemlock.

Socrates was required to pour a draught of hemlock down his own throat, froma cup he held in his own hand, with the full knowledge of what the consequences of those swallows would be.

The thing about hemlock is it triggers paralysis of the body while the mind stays perfectly alert.... so, at all times you understand what is happening as your body slowly shuts down and you drown in the fluid that collects in your lungs.

This, to me, sounds perfectly horrid, similar to the shut-in syndrome that some stroke patients suffer from.

These nasty thoughts, naturally, (strychnine is naturally derived from Strychnos nux vomica, the strychnine tree, from Asia, whilst hemlock is naturally derived from poison hemlock, conium maculatum) led me to the Italian wine/poison, cantarella.

Cantarella was the fabled poison of the Renaissance Spanish/Italian Borgia family.

The House of Borgia came to prominence with election of one of their own, Alfonso de Borja (1378-1458), as Pope Calixtus III (1455-1458).

Ensconced in Italy, after moving with Alfonso de Borja from Valencia, Spain, the House of Borgia became known for their political prowess which allowed them to get another member of the family elected as Pope; Rodrigo Borgia (1431-1503) became Pope Alexander VI (1492-1503).

More accurately, the Borgias become notorious for the way that people who opposed them, or who stood in their way, or who possessed large sums of liquid cash (which the family would later seize) would die.

By poisoning.

The Borgias are believed to have made a mixture of arsenic and wine which they would give to people, and this poison became known as cantarella.

The Borgias reputedly experimented on animals and, later, on people, to determine how to vary the dosages so that the poison would (a) not be detected, and (b) they could determine beforehand when their victim would die.

Knowing when death would occur was good for both building alibis and for arranging votes, or transfers of funds...

The recipe of cantarella has been lost to time but it is rumoured that it involved arsenic which had been rendered more efficacious by being mixed with the entrails of animals and squeezed out in solution...

What is known is that cantarella remained tasteless and undetectable when added to red wine.

The Borgias were a bit like the spinster Brewster aunts from Joseph Kesselring's "Arsenic and Old Lace".

But, far more successful.

And, who would refuse a dinner with the Borgias?

It is a bit hard to imagine any Westerner, during the Renaissance, refusing a dinner with the Pope or with one of his family members.

You are likely wondering where this is all heading, today.

Well, all this thought of poisoning, and of food, brings to mind a bit of poisoning your humble scribe experienced, a while ago.

Food poisoning, yes, but more in the sense of the Borgias. And, more natural.

Do you want to know more?

Same time, Friday.

After 3WW on Wednesday.

I'll tell you all about it, then.


Click to hear 'Love Potion No. 9' by The Coasters 'cause you have to love something to kill for it, no? Even if it's just the thrill... iTunes


Friday, December 11, 2009

On Pelletier and Caventou, malaria, syphilis, and a gin and tonic

Image of the Hong Kong Island skyline from the lounge of the Intercontinental Hotel in Hong Kong. This image is entitle 'Relaxing in the Intercontinental Hotel in Hong Kong with my Dad and a gin and tonic. This really gives you an idea of just how big IFC2, in the far right of the skyline, is'.Dear Gentle Reader,

Your humble scribe has mentioned, in passing, the British, in India, before.

And we have glossed over the quinine they took, as tonic water, combined with that Dutch poison, gin.

The British dosed their bitter medicine (quinine dissolved in carbonated water--tonic water) with gin to make it, the quinine, more palatable.

But, what is quinine? Where is it from? Why do we all know its name?

Quinine is a medicine used to combat malaria, which, with all our drugs and skills and knowledge, today, is still a significant global killer.

Malaria was even more feared before reliable medicines were known.

But, that doesn't tell us much about what quinine is.

Image of the quinine molecule sourced from the Wikimedia Commons; in the public domain.Quinine, C20H24N2O2, is an alkaloid derived from a plant.

It was isolated in 1820 by Pierre-Joseph Pelletier (1788-1842) and Joseph-Bienaimé Caventou (1795-1887), two French chemists who worked in Paris.

Those gentlemen were great.

They isolated quinine to treat malaria.

They also isolated brucine, a poison, that would later be used, in small doses, to treat and regulate blood pressure.

(Brucine also regulates blood pressure when administered in large doses, but it does so in a more permanent and unpleasant fashion).

Pelletier and Caventou also isolated strychnine to treat rats and other rodents.


(People were treated with strychnine, too. The less-reputable Dr. Thomas Neil Cream (1850-1892), the Lambeth Poisoner, murdered many women, and a few men, as a way to treat the world and purge sexual sin...)

Pelletier and Caventou even isolated chlorophyll.

Chlorophyll is not just the stuff that freshens your breath in some breath mints.

Chlorophyll is the green chemical that allows plants to convert CO2 and water (H2O) into sugar n(CH20) and O2; chlorophyll allows plants to turn sunlight into chemical energy which is rather important for ecosystems on earth.

That chemical reaction, as an aside, written out, looks something like this:

6CO2 + 6H2O + photons (light) → C6H12O6 + 6O2

But, without the chlorophyll, nothing happens. That arrow requires chlorophyll, the catalyst in the equation.


Love those plants.

Treat them well.

(Give peas a chance.)

Finally, Messers Pierre-Joseph Pelletier and Joseph-Bienaimé Caventou even isolated caffeine, a very valuable chemical in the modern world.

Your humble scribe remembers isolating caffeine in an organic chemistry lab a long, long time ago.

Hours of work for a little bit of powder.

I apparently loved the labour, though; I stayed up for a week afterwards.

But, back to quinine.

Quinine was a far more valuable chemical in Pelletier and Caventou's time than caffeine is in our time.

In 1820, quinine, C20H24N2O2, was a very big deal.

Why? Because of malaria.

Malaria was, and had been, a scourge to Europeans scouring the globe for opportunities evangelical, mercantile and sovereign.

The bacteriological agent, Plasmodium, which was responsible for malaria and which was transmitted by the Anopheles mosquitoes (but only by the ladies), would not be discovered until 1880 by Charles Laveran (1845-1922).

However, the Jesuits had made a remarkable discovery, in Peru, early in the seventeenth century.

The Jesuits discovered what the Quechua Indians of that Spanish possession, Peru, knew. They learned that if you boiled the bark of what became known as the Cinchona shrub/tree you might be able to cure a malaria victim.

The mythical, Western origin legend was that the Countess of Chinchona, wife of the Spanish Viceroy to Peru, was cured of malaria by the Quechua Indians and, hence, later, Carolus Linaeus would name the shrub/tree Cinchona.

(Isn't it obvious that the miracle plant would be named after the Western victim rather than the people who supplied the information? No? Go back to your history books!)

Jesuit's bark (later, Cinchona bark) became known in Europe as the cure, and as a possible prophylactic, or preventative treatment, against malaria.

The prophylactic treatment came from the work of one Dr. Christian Hahnemann (1755-1843), the father of homeopathy--the concept that like cures like.

The historical pre-foundation of homeopathy can be found in the English expression "the hair of the dog" which refers to the idea of taking a stiff drink in the morning to ward off a hangover from the night before.

Its etymology was the ancient belief that if you were bit by a dog, you should cut out some of the hair of the dog that bit you and stuff that into your wound to ward off disease, especially rabies.

This treatment came from Roman times as an example of the medicinal rule similia similibus curantor, or like cures like.

Dr. Hahnemann, a German physician, noted that cinchona could not only cure malaria, but if taken in large doses by a healthy person, cinchona would induce the same symptoms as malaria.

Recalling the old Roman adage, and modern, recorded observations, Dr. Hahnemann founded the medicinal science of homeopathy--from observations on the curative, and causative, properties of cinchona bark.

So, remembering that the active ingredient of cinchona bark, essentially, was quinine--quinine could be argued to the root (though it comes from bark) of homeopathy.

More things should be noted about malaria and quinine.

Another scourge of Europe, and the world at that time, was the pox, women's pox, the scourge.... syphilis.

(An aside, while malaria really is only spread by ladies, lady Anopheles mosquitoes, that is, it was believed for a long time that syphilis was only spread by ladies which was why it was called woman's pox.)

Syphilis was painful, virulent, incurable, and fatal.

People tried cures, like injecting large quantities of mercury up men's urethras, and tried prophylactics... like condoms made from fishskins... with the scales still on... or from the intestines of sheep, or lambs... an interesting origin theory, perhaps, for the slang terms alluding to a phallus as a sausage....

But, sadly, none of the cures or prophylactics worked.

Then it was discovered, perversely, that a malarial infection would kill a syphilis infection.

Although the patient would still die.

Until Jesuit's bark came along, however, because powdered cinchona helped some people survive malaria.

So quinine, the isolated active compound from cinchona bark, or Jesuit's bark, had a monumental impact on the world.

Now that malaria could be cured, it was easier, or at least safer, to explore the world and to extract wealth from it.

Further, one could now fornicate with abandon.

Life was looking up.

(Especially now that scratchy fish-scale condoms could be abandoned.)

Based upon Dr. Hahnemann's theories of homeopathy, people took quinine as a prophylactic against getting malaria, especially when they were abroad.

Grains of wildly bitter quinine were given to members of the Indian Army and the Indian civil service.

Enlisted men had to take the quinine on their parade grounds, under the watchful gaze of their officers, as the medicinal quinine was so stupefyingly bitter that some would try to not take it.

Wealthy British planters in India consumed large quantities of gin to help the bitter quinine grains go down. And they found that gin went well with the bitter taste of quinine.

Eventually some clever chap thought of brewing up bark from the remijia tree of Peru so that people could have a better bitter tonic, and by better, I mean cheaper.

Remijia is a relative of the cinchona shrub/tree. It has a more bitter taste than cinchona bark and while it has some quinine in its bark, it has less quinine that cinchona...which makes remijia relatively cheaper although more flavourful. And the name of the game in advertising is not reality, but appearances.

The new tonic water from remijia bark tasted more of quinine than cinchona bark did, although it actually had less, so it was ideal for a mass distributor of a bitter, quinine flavoured tonic for profit.

And thus Indian tonic water, and hence a gin and tonic, was born.

And why did your humble scribe go off on that long, earlier, laudatory aside on Messers Pierre-Joseph Pelletier and Joseph-Bienaimé Caventou?

...Beside the fact that quinine had a monumental impact on the world from curing and preventing malaria, to curing syphilis, to creating the gin and tonic cocktail...

Because, after Pelletier and Caventou had isolated quinine, the key to combatting malaria, and, circuitously, syphilis, Pelletier and Caventou freely gave their knowledge away to the world.

Their benefit was seeing the world benefit.

I think that that is worth a laudatory aside for those two gentlemen.


Charge your glass with some gin.

And some tonic.

And join me in a toast to Pelletier and Caventou.


And the music for today...

Click to hear 'Root Trees' by Shawn Lee & Clutchy Hawkins


Image of the Hong Kong Island skyline from the lounge of the Intercontinental Hotel in Hong Kong, again, after dinner. This image is entitle 'See? Gin and Tonics make everything better... Next stop, Nobu's...'.