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Author: Subject: Medicinal Compounds of Natural Origin
Aloesci
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[*] posted on 3-5-2021 at 09:49
Medicinal Compounds of Natural Origin


I'm interested in pharmacology and I've been starting by extracting compounds from natural sources which are used medicinally.

I recently moved onto Quinine, a historical anti-malarial drug which isn't used so much anymore because it can cause irregular heartbeat problems. It's found in the bark of a tree from south america, and i played around until i was able to extract some. I made a video about the process, but i can write it up if anyone is interested:

https://youtu.be/Z23WEOwkRwk

Anyway, i'm wondering if anyone knows of any interesting sources of natural alkaloids or other medicinally useful compounds?

Also, any stories of efforts to make useful compounds with home chemistry for end-of-the-world scenarios? ;)

Ofc its stupid to ingest or use things you make without heaps of purification/analytical steps to make things safe, but i'm curious nonetheless.
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njl
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[*] posted on 3-5-2021 at 10:23


I think you and symboom would get along nicely. Here's his post related to this topic, I believe there is some discussion of natural sourcing in there.



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Aloesci
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[*] posted on 5-5-2021 at 11:59


Fascinating post, thanks!

I have an idea now to try and obtain a histamine antagonist found in onion skin called quercetin.
Apparently it can be extracted with cold ethyl acetate, which gives me a reason to make some more ethyl acetate.

Theres so many compounds out there which nature just makes using biochem that would take us ages to come up with a synthesis pathway for. The crazy thing is sometimes we don't know why plants and other life make so many compounds.

I'm always open to new ideas for trying extractions and syntheses.
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Mr. Rik
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[*] posted on 5-5-2021 at 15:41


Nice video. I am also developing an ever growing interest in this topic. Would love to see more related content.
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symboom
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[*] posted on 5-5-2021 at 20:12


This is great to hear I hope it inspires others interest in it. It sure helped me alot and helped me with understanding neuroscience better.

histamine antagonist found in onion skin called quercetin.
That's interesting I've seen quercetin being sold as a supplement I didn't know it was a neuroreceptor chemical.




[Edited on 6-5-2021 by symboom]




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Aloesci
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[*] posted on 6-5-2021 at 13:00


Thank you Mr. Rik!

Symboom, from some papers I've found online it looks like the compound Quercetin doesnt so much interfere with any histamine receptors as it just inhibits histamine and heaps of other chemicals which cause inflamation from being released from mast cells in the first place. It seems to do this by inhibiting receptors for IgE on the mast cells which normally mediate this release. I suppose the difference between Quercetin and typical antihistamines like loratidine would be that whereas antihistamine drugs are often competitive inhibitors for specific H1 (histamine) receptors, Quercetin may reduce overall inflamation caused by histamine and those other compounds released by mast cells.
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medchemist
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[*] posted on 3-6-2021 at 14:04


There are quite a few compounds that fit your interest. I would recommend finding a book on pharmacognosy (https://b-ok.cc/s/pharmacognosy ought to have some good ones) as that is the study of natural sources of drugs!

There are few drugs that are still clinically used in their natural form as medicinal chemists tend to use them as a template then modify them to give them improved properties that make them more suitable for clinical use. Notable exceptions are morphine, atropine, cocaine, chloramphenicol, streptomycin and as you point out, quinine. Although all of these (apart from perhaps morphine in some places) are not a first line treatment as there is a better synthetic/semi-synthetic drug available.

There are many semi-synthetic drugs, i.e. the starting material is naturally occurring such as many antibiotics (many of the penicillins and tetracyclines), opiates (I would advise against trying to source and extract natural opiates for obvious reasons...) and curare analogues (used as paralytic agents in anaesthesia). These provide a nice insight into structure based drug design which your quest will inevitably lead you to if it hasn't already.

If you find some old (pre 1950s) pharmacopoeias there will be many more drugs of natural origin listed that are not modified in any way as this modification is relatively new science. Before then we entirely relied on nature to create potent compounds that, when used purified and used correctly, provided clinical benefit. This would be a good source of information for your hypothetical " efforts to make useful compounds with home chemistry for end-of-the-world scenarios?"
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[*] posted on 3-6-2021 at 14:09


I made ibogaine semisynthetically, from voacanga root/stem bark, first by extraction of the voacangine and then by ester hydrolysis followed by decarboxylation.
I only got an amount of 440mg(ibogaine HCl) in the end though, from ~350g of the bark powder.

[Edited on 3-6-2021 by karlos³]
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Aloesci
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[*] posted on 7-6-2021 at 22:44


I finished my project on quercetin from onions! Made a video too:

https://youtu.be/89aFp9t45j8

Pharmacognosy sounds so interesting! I didn't realise it was as extensive as an entire field of its own. I think one thing that stops drug companies now from going all out into such research is that you can't always patent what you find in nature, which is a shame because I've heard some things are even better than synthetic drugs.

I'm having a few issues with re-crystalisation on small scales. How do you know how much solvent is the minimum amount to add to disolve your compound? And how do you keep it hot while you disolve the compound? I've been using a hotplate but my solvent often boils as I'm trying to disolve my compound. Any tricks or advice to get a nice recrystalisation technique down on small scale?
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[*] posted on 13-8-2021 at 10:31


1) How about making some ivermectin ? From a cursory read I have had it is the hydrogenation of avermectin, which you get from a bacteria, Streptomyces avermitilis.

2) I have watched your vid on quinine, well done. I am doing the same atm, only I will use soxhlet extraction and will try to isolate cinchonine and cinchonidine just for self sadism.




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AJKOER
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[*] posted on 16-8-2021 at 14:00


I feel obligated to supply the following to my readers as I feel personally to have more recently, after several months of use, seemingly benefited from an extract of this old Chinese herb derived from the bark of a common tree.

The product, cheaply available from Life Extension (a major Vitamin supplier), is called Dopamine Advantage.

Here is a quote from a news release at https://www.globenewswire.com/en/news-release/2021/03/09/218...

"Fort Lauderdale, FL, March 09, 2021 (GLOBE NEWSWIRE) -- To help maintain healthy levels of dopamine in the brain, Life Extension has introduced Dopamine Advantage, an innovative formula designed to support cognitive performance, mood and overall brain health.

Dopamine is a neurotransmitter, or chemical messenger, well-known for its role in how we experience pleasure. Eager anticipation of eating, having sex, and getting positive comments on social media all involve the release of dopamine in specific areas of your brain. And, it turns out that this neurotransmitter is also essential to how you think, plan and focus. Unfortunately, levels decline over time.

To promote healthy dopamine levels, Life Extension’s Dopamine Advantage combines phellodendron tree bark and vitamin B12 as adenosylcobalamin. According to recent research, these two nutrients can support the brain’s levels of dopamine to help maintain overall cognitive health, contributing to positive mood while performing and focusing optimally.

“We chose these nutrients specifically for their potential to maintain healthy dopamine levels in the brain,” said Dr. Andrew G. Swick, Life Extension’s Chief Scientific Officer. “This represents an innovative new addition to our brain health product category”

A study published in 2016 in the European Journal of Medicinal Plants showed that Phellodendron amurense can inhibit an enzyme called monoamine oxidase-B (MAO-B for short). This enzyme breaks down dopamine, lowering the amount that's available to your brain cells. Meanwhile, a 2019 study in Cell Research showed that the adenosylcobalamin form of vitamin B12 prevented another enzyme, Leucine-Rich Repeat Kinase 2 (LRRK2), from depleting dopamine levels.

According to Life Extension’s Director of Education, Dr. Michael Smith, the new formula will benefit consumers seeking to maintain healthy levels of dopamine. “As a neurotransmitter, dopamine is produced in the brain and released into the synaptic gap, the microscopic space between neurons, relaying information from one neuron to the next,” he explained. “But factors such as nutrition deficiency, aging, environmental changes and stress can cause a decline in dopamine levels, affecting cognitive performance and motivation That’s why supplementing with nutrients that support cognitive health and complement a healthy lifestyle is important.”

There was also an associated Life Extension magazine article on this compound. In particular, the article cited a study on older rats, where the herb produced a 50% further increase in the aged rat's longevity in the group receiving the Dopeamine. No associated study in humans.

This new source of a dopamine derivative appears to be only recently discovered in the bark of a tree (common to China). The latter bark, per my recollection, has also been long known to have medicinal value.

As such, you may further be interested in investigating extraction techniques of this possibly valuable herbal bark and its use in combination with other compounds.
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[*] posted on 17-8-2021 at 07:20


I recently moved to a new area and have found myself surrounded by pharmacologically-active plants and fungi that i've never experienced in the wild before. It's helped make up for the lack of human contact that I've had since getting here. Two species that I am particularly interested in currently:

Ghost Flower (Monotropa uniflora) aka Ghost Pipe: I've seen quite a bit of this in the damp valleys and draws in forests. Traditional use seems to be as an anti-anxiety treatment as well as a hypnotic/sedative. It has also been noted as a traditional treatment for epilepsy.

"An infusion of the root is antispasmodic, hypnotic, nervine, sedative, and tonic.
It is a good remedy for spasms, fainting spells and various nervous conditions.
It has been given to children who suffer from fits, epilepsy and convulsions.
Plant was used by some native North American Indian tribes to treat eye problems, the stem was bruised and the clear fluid of the stems applied to the eyes.
Juice from the stems has also been used to treat nervous irritability, including fits and spasms."

Second species is the Ink Cap Mushroom (Coprinopsis atramentaria). I've seen this around as well and it has a SUPER interesting characteristic. It is edible without negative effect UNLESS you have ingested alcohol. It contains a compound called coprine which can cause the "Coprinus syndrome" when ingested with alcohol; essentially its metabolite blocks acetaldehyde dehydrogenase from breaking down acetaldehyde in the ethanol metabolism process, so instead of alcohol poisoning, you suffer from acetaldehyde poisoning. And yes, it has been used as a rudimentary treatment for alcoholism...seems like a "Clockwork Orange" type of solution if you ask me!

This entire subject is of immediate interest to me, and I'm interested to hear about what other people have been looking into
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