Sciencemadness Discussion Board - What would you do with a field of hemlock?

What would you do with a field of hemlock?

White Yeti - 7-5-2012 at 12:36

Spring is here, and the water hemlock has returned. Year after year, tons of water hemlock grow in my yard and I've wondered if there is something constructive I can do with all that toxic plant matter.

The obvious use of hemlock is poison. However, I'm wondering if cicutoxin has any other uses, namely in organic chemistry. All those double and triple bonds in cicutoxin make me wonder if this molecule can be used in organic syntheses.

The greatest concentration of cicutoxin is in the roots, and I'm estimating I can dig up at least 20 pounds of roots in my yard alone. If I were to go to the banks of a river nearby, I'd be able to get over a hundred pounds, so availability is not an issue. This stuff grows everywhere.

Any ideas?

bahamuth - 7-5-2012 at 14:23

There would be tons of stuff to do with it, but would it be worth the risk to be exposed by the toxins?

The only really cool think I can come up with is to try to isolate it and purify it by various means. Write a method paper and post it to SM and other places on the net to insure immortality of your work.. But then again, exposure comes to mind..

Edit:

Polymerization might perhaps be fun to try, if there is enough of it in the plant.

[Edited on 7-5-2012 by bahamuth]

watson.fawkes - 7-5-2012 at 17:54

Quote: Originally posted by White Yeti

All those double and triple bonds in cicutoxin make me wonder if this molecule can be used in organic syntheses.

Seems like a reasonable substrate to practice hydrogenation upon. With a pair of triple bonds, I would imagine that the first few hydrogens attach readily and under much milder conditions than ordinarily seen, requiring a pressure vessel.

The main product you'll get is practice.

White Yeti - 7-5-2012 at 18:21

Quote: Originally posted by bahamuth

There would be tons of stuff to do with it, but would it be worth the risk to be exposed by the toxins?

I think that there might be a few risks involved with handling this substance, but I'm under the impression that it's easily degraded by heat and enzymes, which limits the danger of long term exposure to small amounts.

Then again, as a very potent poison with profound effects on the nervous system, you don't need a lot of this toxin to drop dead. Although the LD50 is quite high for a poison, 48.3 mg/kg according to this source. For someone my size, you'd need ~2.4g of pure cicutoxin, which is quite a bit of toxin.

@watson.fawkes

Hydrogenation is a good idea, that's if the triple bonds don't break in the extraction process.

Pyridinium - 7-5-2012 at 19:32

When I saw this post I thought "hemlock trees", and I immediately thought "acetic acid, creosote, and methanol". As for that nasty weed that killed Socrates, I'd be thinking in terms of eradicating it with said acetic acid.

Then, of course, destructive distillation to yield more acetic acid, methanol, etc.

:-D

I don't know if that LD50 extrapolates to humans, because I've read that you shouldn't even touch the plant with bare hands. All the more reason for spraying it.

bahamuth - 7-5-2012 at 21:11

Quote: Originally posted by White Yeti

Although the LD50 is quite high for a poison, 48.3 mg/kg according to this source. For someone my size, you'd need ~2.4g of pure cicutoxin, which is quite a bit of toxin.

Human Toxicity Excerpts:
/HUMAN EXPOSURE STUDIES/ Ingestion of as little as a 2 cm section of the sweet-tasting root of Cicuta can produce fatal status epilepticus; a child's use of a stem as a toy whistle caused the child's death. The cause of seizures is not clear but may be from central cholinergic overstimulation, sodium channel effects, or blockade of potassium dependent channels.
[Goldfrank, L.R. (ed). Goldfrank's Toxicologic Emergencies. 7th Edition McGraw-Hill New York, New York 2002., p. 1168] **PEER REVIEWED**

Non-Human Toxicity Excerpts:
/OTHER TOXICITY INFORMATION/ ...The minimum lethal dose of cicutoxin for all species is of the order of 50-110 mg/kg body weight and a piece of the fresh root the size of a walnut is considered to be fatal to horses and cattle. ...Pigs are /believed to be/ more resistant than most species.
[Clarke, M. L., D. G. Harvey and D. J. Humphreys. Veterinary Toxicology. 2nd ed. London: Bailliere Tindall, 1981., p. 258] **PEER REVIEWED**

There is some discrepancies in this text, a walnut size peice of wet soft root is by me estimated to be around 25 grams, and it will kill a horse (somewhere between 400-800 kilos) and cattle which may even double that weight. So the supposed LD100 for a horse at 400 kg is 25g root material?? With data from the same text LDmin is about 20000 mg of the actual toxin, and this makes me wonder, is the root completly composed of the toxin?

I think the LD50 of 48.3 mg/kg is of the root material itself and not the toxin and as such it increases the danger factor by perhaps 100 IMO..

I'd rather play around with cyanide since it has a good set of antidotes, than that stuff....

Slink - 17-1-2013 at 03:12

what species is it as there are 3 related plants that all look similar (from a far)

if it is Hemlock (aka poison hemlock) it will smell of mice and has purple/red splotches on the stem. The toxin in this one is coniine

the other two are extremely similar looking and too add confusion are both known as water hemlock...

Cicuta (cowbane/water hemlock) has smooth stems and a parsnip like tap root with hollow segments and the sap smelling of parsnips/carrots

Hemlock water drop wort has grooved stems that look like celery and roots that look like a bunch of white carrots (said to be the most toxic of the three)

the similarities dont end there between Cicuta and hemlock dropwort, the toxins are extremely similar too, the only difference between Cicutoxin and Oenanthotoxin is a double bond between the 15th and 16th carbon (cicutoxin doesnt have this extra bond) and that it!!! D:

if it is one of these and you plant to do extracts then do it on a gloomy day as the toxins are most concentrated then

hissingnoise - 25-1-2013 at 04:20

Quote:

In the past it found uses as arrow poison, whistles and peashooter.

Peashooters from hollow stems! Wow a real blast from the past?
Never knew back then that we kids were, when given the opportunity, sticking poisonous plant-stems in our mouths . . .
And very good peashooters they made, too!

morganism - 29-1-2013 at 23:24

Well, atropine from datura is a antidote to nerve poison gas.

It's possible that this could also be a beneficial in the correct frame.

Possibly a cns depressant overdose reversal ?

Didn't know about the mouse smell....

Lanafan10 - 15-5-2013 at 10:36

How do you extract cicutoxin from the water hemlock plant?

Bot0nist - 15-5-2013 at 12:32

http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~n2lRK...

You should be able to figure it out quite easily, with this page, and some basic knowledge of plant extractions. Don't be lazy AND homicidal...

chemcam - 15-5-2013 at 12:40

Quote: Originally posted by Bot0nist

http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~n2lRK...

You should be able to figure it out quite easily, with this page, and some basic knowledge of plant extractions. Don't be lazy AND homicidal...

That link won't work for me, I get the following error: "Your search has expired. Please resubmit your search."

Also, my your name , "bot0nist" I assume botany is something you enjoy, me too. Do you have any good resources for plant identification based of region and other info, I want to see what is local for my area, and what I can do with it. There are so many sites with conflicting info i'd like to use one that an experienced botanist would use. I am just beginning so I know absolutely nothing about plants.

[Edited on 5-15-2013 by chemcam]

Lanafan10 - 15-5-2013 at 13:02

Thank you that is what I wanted I small bit that will make me think and that is why I wanted to know so that I could test my skills. I'm not homicidal lol but some on this seem that they are lol. Thanks again.

Lanafan10 - 15-5-2013 at 13:07

I was thinking drying and powdering water hemlock, wrap it in filter paper and place through the extraction process using pure alchol and go from there maybe a similar process to the extraction of glycosides?

Lanafan10 - 15-5-2013 at 13:09

Soxhlet extraction process*

Bot0nist - 15-5-2013 at 13:22

search the chemical name in the search field on that site, then view the chemical properties... Sorry about that.

Bot0nist - 15-5-2013 at 15:14

Quote: Originally posted by chemcam

Quote: Originally posted by Bot0nist

Hey chemcam, while I do not have a degree in botany, I have workered in the horticulture, botanical, and nursery industries my whole adult life. Mostly in a tropical greenhouse as a propagation manager. Not bad work, if you like wearing shorts and T-shirts all year. It has been compared to "Hell," as it is about 90F and all 85% humidity all day, everyday and you get to wear a fully sealed yellow "moon suit" when you get to spray chemicals (at least 8 hours a week). Hot as hell and with that humidity, sweating is not effective.

A good place to find a local identification guide would be your local library. I use a book called edible and medicinal plants of the southeast, or something like that. I can't remember the title right now, as I'm at work, but it is usefull. Don't consume anything unless you are 100% sure. Mistakes are costly.

I love plant extractions and steam distillations to get natural reagents and starting points for synthesis. I was even privy to a large scale extraction of alkoloids from bulk papavar straw. Very interesting indeed.

To all those attempting to isolate deadly compounds, please be very careful and make sure your procedure is flawless. One slip up, and your a Darwin award winner... Oh, and don't be murdering...

[Edited on 15-5-2013 by Bot0nist]

Lanafan10 - 15-5-2013 at 23:23

I was thinking drying and powdering water hemlock, wrap it in filter paper and place through the soxhlet extraction process using pure alchol and go from there maybe a similar process to the extraction of glycosides? Would that be along the right lines?

PHARMAHERBAL - 27-8-2013 at 07:27

HEMLOCK IS VERY TOXIC BURN YOUR FIELD WARE A RESPIRATOR AND GET BACK TO YOUR SNOW CAVE only messing with you but it is a herb well avoided

Eddygp - 23-9-2013 at 11:38

How about cyclization of this molecule? Might be interesting. As well as hydrogenation. Get rid of those double and triple bonds!