Sciencemadness Discussion Board

Scopolamine (Ester to Carboxylic acid)

UndergroundChemist - 25-4-2014 at 05:23

Ok so I have put so me stupid shit on this forum before but now I have read some more about reactions and how it works and then according to This I should be able to turn the ester in Scopolamine to a carboxylic acid and break the Oxygen bond with a Aq solution of an acid or base and heating which would hydrolyse the ester to carboxylic acid.
This would be correct right? and the structure would be:




Why I chose Scopolamine is because I have a whole plant full of it and I don't want all that nasty stuff :S It's some scary shit. So why not make something else out of it?
Cheers

[Edited on 25-4-2014 by UndergroundChemist]

Bert - 25-4-2014 at 06:00

Before figuring out how to monkey wrench on the molecule, how would one extract it from the plant material and purify it?

I keep thinking of this little poem I learned in the ER:

"blind as a bat, mad as a hatter, red as a beet, hot as hell, dry as a bone, the bowel and bladder lose their tone, and the heart runs alone.”

Mildronate - 25-4-2014 at 10:33

For atropine there is one synthetic analog http://ru.wikipedia.org/wiki/%D0%90%D0%BF%D1%80%D0%BE%D1%84%...

forgottenpassword - 25-4-2014 at 11:23

It would be more worthwhile to extract and purify scopolamine, rather than turn it into the useless product that you propose. You will learn more chemistry by carefully extracting a useful product, rather than destroying it with drain cleaner!

[Edited on 25-4-2014 by forgottenpassword]

Pickardjr - 25-4-2014 at 16:56

Scopolamine is some nasty dangerous stuff. If it gets air born and you inhale it, the tiniest amount will probably kill you. But before you die you will have the most hellish trip. Are you experienced in handling incapacitating agents such as this? I advise you to re-think this one.

If, and I mean If you had the skill to refine scopolamine to a HCL or sulfate crystal it would be too dangerous to handle, let alone any chemical manipulation. You would need FULL protective gear like a bio -hazard to keep from killing yourself in the process.

smaerd - 25-4-2014 at 20:13

Judging by the synthetic chemistry question... I'd venture to say that the OP should be nowhere near such a process, let alone trying to conduct it. Then again I guess, purely academic questions of almost any variety are tolerated here? I would expect epimerization of the alpha methyl hydroxy. Although, yea I see no reason why acid/base hydrolysis wouldn't work on an ester. Might have a competing enolate depending on the conditions. Then again I'm too tired and lazy to think about the likelihood of that, so call that unsubstantiated speculation(useless/bad advice/misleading/synonyms here).

Nicodem - 25-4-2014 at 23:56

Please let's not overreact and issue dramatic danger warnings to someone who is obviously too clueless to ever even manage a scopolamine isolation, let alone any synthetic use of such a hazardous compound. If UndergroundChemist really had the competence to perform anything of what he talks about, then he would also have the competence to search the literature for the scopolamine isolation and hydrolysis procedures (and would not need to open this topic). It is obvious he is just a teenager who has knows nothing about practical chemistry (also because only a teenager could have chosen such a nickname). Bear with him and rather try to educate him by pointing him to the literature and experiments proper to his age.

UndergroundChemist, please start by reading the forum guidelines and in particular the literature searching guidelines in the same thread. The best way to learn something is to first start learning. Also, when you open a new thread, you are expected to cite proper references. Just adding a trivial link to some educational site talking about hydrolyses is not relevant at all. You should at least do some basic literature work and review the topic before asking others for help or advice. If you feel too lazy or too incompetent to review the topic, you can always open the thread in the Beginnings section.

UndergroundChemist - 26-4-2014 at 06:36

Quote: Originally posted by Nicodem  
Please let's not overreact and issue dramatic danger warnings to someone who is obviously too clueless to ever even manage a scopolamine isolation, let alone any synthetic use of such a hazardous compound. If UndergroundChemist really had the competence to perform anything of what he talks about, then he would also have the competence to search the literature for the scopolamine isolation and hydrolysis procedures (and would not need to open this topic). It is obvious he is just a teenager who has knows nothing about practical chemistry (also because only a teenager could have chosen such a nickname). Bear with him and rather try to educate him by pointing him to the literature and experiments proper to his age.

UndergroundChemist, please start by reading the forum guidelines and in particular the literature searching guidelines in the same thread. The best way to learn something is to first start learning. Also, when you open a new thread, you are expected to cite proper references. Just adding a trivial link to some educational site talking about hydrolyses is not relevant at all. You should at least do some basic literature work and review the topic before asking others for help or advice. If you feel too lazy or too incompetent to review the topic, you can always open the thread in the Beginnings section.

No it's not that I'm to lazy or anything. And well I'm not really asking for help just someone who can confirm that this would work. I have added links / references..

UndergroundChemist - 26-4-2014 at 06:40

Quote: Originally posted by forgottenpassword  
It would be more worthwhile to extract and purify scopolamine, rather than turn it into the useless product that you propose. You will learn more chemistry by carefully extracting a useful product, rather than destroying it with drain cleaner!

[Edited on 25-4-2014 by forgottenpassword]

How do you know that it will be useless?? It could probably produce some effects similar to scopolamine...
I have extracted scopolamine before without any problems using ethanol and diethyl ether to get rid of oils. But I know atropine and other stuff will also be left in the ethanol solution

Bert - 26-4-2014 at 07:26

The stuff isn't going to rise out of the flask and chase you down to murder you- but it IS pretty nasty.

If you ever did such a thing, have Physostigmine and Benzodiazepine available, and don't work alone.

So, after removing the alcohol soluble components (which alcohol? What salt of the target material has the best solubility?) (and probably doing repeated vacuum filtration of the alcoholic solution obtained through activated charcoal for removal of chlorophyll and other "gunk"), one distills off the ethanol (how heat stable is the target material? Do you need vacuum, or will atmospheric pressure be OK?), then does a water/ether extraction?

Which layer carries the target material?

What ELSE does that layer contain? :o

Can you afford, do you KNOW HOW TO RUN a chromatography column?:(

Since you can't/don't- How did a 19th century manufacturing chemist proceed?

This is all well established pharmaceutical/industrial chemistry. Tons of literature in the public domain.

Let's see how many of those question marks you can put to rest- And along the way, you'll learn something.

Does it work like this?

UndergroundChemist - 26-4-2014 at 08:05

okay so lets say I have a compound that contain an ester like Leonurine or Propyl acetate or basically any compound that contain an ester group. Would any compound that contain an ester group be able to undergo an Ester hydrolysis?
and break the O bond to R and form a OH there instead.
which would mean the chain(r) would be removed from the molecule?

thesmug - 26-4-2014 at 09:43

Yes, since ester hydrolysis hydrolyzes esters...

Chemosynthesis - 26-4-2014 at 12:52

Quote: Originally posted by UndergroundChemist  

How do you know that it will be useless?? It could probably produce some effects similar to scopolamine...
I have extracted scopolamine before without any problems using ethanol and diethyl ether to get rid of oils. But I know atropine and other stuff will also be left in the ethanol solution


1. Because of pharmacology. The chemical you have is an isomer of tropic acid, and it's a common pharm chem reagent with well known properties.
2. Partial workup=/= extraction. Likewise, your links aren't really considered literature. I highly recommend you take a chemistry class before posting more hand-holding requests on pharmacologically relevant substances. I had to go to school (and lots of it) for such topics, and expect no less of anyone else.

UndergroundChemist - 26-4-2014 at 13:40

Quote: Originally posted by Bert  
The stuff isn't going to rise out of the flask and chase you down to murder you- but it IS pretty nasty.

If you ever did such a thing, have Physostigmine and Benzodiazepine available, and don't work alone.

So, after removing the alcohol soluble components (which alcohol? What salt of the target material has the best solubility?) (and probably doing repeated vacuum filtration of the alcoholic solution obtained through activated charcoal for removal of chlorophyll and other "gunk"), one distills off the ethanol (how heat stable is the target material? Do you need vacuum, or will atmospheric pressure be OK?), then does a water/ether extraction?

Which layer carries the target material?

What ELSE does that layer contain? :o

Can you afford, do you KNOW HOW TO RUN a chromatography column?:(

Since you can't/don't- How did a 19th century manufacturing chemist proceed?

This is all well established pharmaceutical/industrial chemistry. Tons of literature in the public domain.

Let's see how many of those question marks you can put to rest- And along the way, you'll learn something.

I'm not really looking to get 99% pure scopolamine. But you have a point with all that but I'm 15 and I'm not looking to go in hardcore I just posted this to check if a theory about a reaction I did was correct. And for all others scopolamine isn't really that dangerous the ld50 is moderate high I would be more scared of the atropine.

Anyway this thread is over I have got enough answers that I wasn't even looking for. I think in the future I'll just do the reaction and see if it worked myself. Cheers

UndergroundChemist - 26-4-2014 at 13:42

Quote: Originally posted by Chemosynthesis  
Quote: Originally posted by UndergroundChemist  

How do you know that it will be useless?? It could probably produce some effects similar to scopolamine...
I have extracted scopolamine before without any problems using ethanol and diethyl ether to get rid of oils. But I know atropine and other stuff will also be left in the ethanol solution


1. Because of pharmacology. The chemical you have is an isomer of tropic acid, and it's a common pharm chem reagent with well known properties.
2. Partial workup=/= extraction. Likewise, your links aren't really considered literature. I highly recommend you take a chemistry class before posting more hand-holding requests on pharmacologically relevant substances. I had to go to school (and lots of it) for such topics, and expect no less of anyone else.

I don't know wtf you're trying to tell me all I know is that small changes in a molecule can make big difference just compare 2c-P with 2c-B it's just 1 difference between them and still they have very different dosages, LD50 and a little change in effects

UndergroundChemist - 26-4-2014 at 13:43

Quote: Originally posted by thesmug  
Yes, since ester hydrolysis hydrolyzes esters...

Thank you that's what I thought but I got so many shit answers on my other thread without any correct answer.

Etaoin Shrdlu - 26-4-2014 at 13:50

Quote: Originally posted by UndergroundChemist  
I don't know wtf you're trying to tell me

Clearly.
Quote: Originally posted by UndergroundChemist  
Anyway this thread is over I have got enough answers that I wasn't even looking for. I think in the future I'll just do the reaction and see if it worked myself.

How exactly are you going to determine if it worked?

Chemosynthesis - 26-4-2014 at 14:20

Quote: Originally posted by UndergroundChemist  

I don't know wtf you're trying to tell me all I know is that small changes in a molecule can make big difference just compare 2c-P with 2c-B it's just 1 difference between them and still they have very different dosages, LD50 and a little change in effects

It's evident you don't 'get it.' I'm telling you that you should get a textbook or attend a course, pay a tutor, etc. to learn more instead of posting a multitude of very basic questions in inappropriate sections of the forum despite being asked to do otherwise.


QSAR between homologs/analogs is very different than two extremely different compounds (i.e. tropic acid and atropine/scopolamine). In these cases, esterifying changes the molecular mass by ~100%, and affects molecular symmetry, as well as the regions of ligand/receptor binding. Not so in the instances you mention.

Chemosynthesis - 26-4-2014 at 14:25

Quote: Originally posted by UndergroundChemist  

Thank you that's what I thought but I got so many shit answers on my other thread without any correct answer.

Maybe if you posted in the correct place the first time, and weren't always posting extremely basic chemistry questions about pharmacologically relevant substances, even ignoring advice on things such as what topics to look up to answer your own questions, and not responding to inquiries of intent....

Edit- and in fact, you were given answers in citations in other threads which you apparently never bothered reading. I know because I provided some, either giving you a citation on something you were mistaken on (Wacker oxidation thread), telling you the subject to look up to answer a question (psilocybin deprotonation), or in one instance giving you the common nomenclature to an unnamed compound so you could debunk your own speculations of psychotropic efficacy.

Not once did you appear interested in furthering your chemical education, but instead getting an expedient answer to one very narrow example.

[Edited on 27-4-2014 by Chemosynthesis]

Mildronate - 27-4-2014 at 06:57

If you are only 15yo you are to young at moment to work with scopolamine, atrophine or other CNC agents. No matter what you say. Its reality!

[Edited on 27-4-2014 by Mildronate]

[Edited on 27-4-2014 by Mildronate]

Bert - 27-4-2014 at 07:53
Quote:

In a controversy the instant we feel anger we have already ceased striving for the truth, and have begun striving for ourselves. -Buddha


OK, let's stick to facts and (edited out, thanks for your help & understanding!).

He will either figure out the local culture, learn to research properly, educate himself or he'll be gone.

There are plenty of whip smart 15 year old kids. Plenty of bull headed ones who won't listen too. Sometimes they're the same kids. If they live long enough for the hormones to settle down, they can sometimes be taught. In the meantime, just ignore anything that's not a direct safety threat to the kid or others and wait for time/biology to change things.






[Edited on 27-4-2014 by Bert]

Pickardjr - 27-4-2014 at 16:10

http://youtu.be/ToQ8PWYnu04

Chemosynthesis - 27-4-2014 at 18:00

Quote: Originally posted by Pickardjr  
http://youtu.be/ToQ8PWYnu04

Just judging from the title, it sounds a little aggrandized. Scopolamine was used in "twilight sleep" anesthesia with morphine, and a variety of anticholinergic drugs have had historical associations with witchcraft and even interrogation. Scopolamine is just one the media seems interested in at the moment.