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InvisibleAsante
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Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future
    #6348163 - 12/08/06 02:21 PM (17 years, 5 months ago)

In this thread, let's discuss Psychedelic drug synthesis. Nothing too practical, certainly not planning any action on the reality level, but let's analyze, discuss and bounce ideas off of one another.

If you like chemistry, and you like psychedelics, this thread might be just what you seek. Read before you write and write for your readers - let's keep the information density of this thread high.

I want to especially welcome chemistry buffs and enthusiasts because though psychedelic, this is first and foremost a science thread.

Gentlemen - shall we?


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InvisibleAsante
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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Asante]
    #6348302 - 12/08/06 03:13 PM (17 years, 5 months ago)

Psychedelics are the fuel of the Psychedelic Revolution. For a motor to run smoothly, you need a good fuel supply. Let me break down some of the problems we face on a global scale.
Let's turn on the world :smile2:

-it would be safe to assume that 5% of the world population is a potential psychonaut, and that of this potential, about 10% is realized. This would mean 300 million potential trippers, and a current active community of 30 million trippers worldwide.

-Some trippers dose high, others dose low. Some dose often, others a few times in their lives. Let's assume that the average tripper uses 10 "standard doses" a year and lets fix this number at the equivalent of 100mcg LSD or 20mg Psilocybin (1/8oz cubies) which is a bit stiff for most but takes the extreme users into account who use more than that.

If you look at the needs of our current community then you see that about 300 million doses are required on a yearly basis, and that this need in decades might increase tenfold.

Zingg! There the logistics problem in turning on the world arises.

300.000.000 doses (300 megadose) is a huge amount of psychedelics. If you fill the void with mushrooms alone, this requires a whopping one million kilos of dried Cubensis mushrooms. In LSD, the strongest psychedelic, 300 megadose represent an annual need for 30 kilos of pure LSD, which in its own way is a logistics nightmare.
And to think that we might on short order need ten times as much.

Mushrooms of these two are the prime candidate for filling most of the void, because the consumers themselves can grow them in their homes, decentralizing the mammoth task of bringing kilotons of mushrooms into this world and distributing them. Mushrooms represent the "ideal solution" when groups of friends take care of their own needs, needing no more supplies than grain, water, kitchenware and a onetime obtaining of spores.

LSD is not cutting it. There are droughts more than there are floods, and floods only happen locally. There just is far greater demand than supply can meet. Because LSD requires unique precursors (lysergic acid amides) which are pretty much under government control, there probably will be no breakthroughs on the lysergic front unless a big organisation learns to produce or synthesize its own ergoloids.

It seems only natural that synthetic phenethylamines and tryptamines will find their natural place on the market, now that the time of them being uncontrolled seem to near its end.

DOC is a fullblown psychedelic which lasts 12-24 hours which is active on the few-miligram level. It was well-received by RC experimenters. It can be approached synthetically in many ways and unlike LSD requires no controllable precursors. This means that the factor which limits LSD synthesis does not exist with DOC. Five pounds of DOC represents one megadose, and to synthesize this amount lies in the capabilities of small groups of friends capable of synthesizing Ecstasy on a kilo scale. Ecstasy has "drug factories" which churn out MDMA in quantities of fifty pounds or more a month. If it were DOC, such a "drug factory" would produce ten megadoses a month and over 100 megadoses a year. This means that one particularly large DOC "factory" could in theory produce the required 300 megadoses a year in DOC alone, which is  about 600 kilos annually.

Still - one megadose has a profound impact on the world. It currently takes care of the annual psychedelic needs of the trippers in a region inhabited by 20 million people, a country the size of Holland.
To name the megadoses of some psychedelics:

One megadose of LSD = 100 grams
One megadose of DOC = 2 kilos (also DOB, DOI)
One megadose of 2CP = 7.5 kilos
One megadose of 2CE = 12.5 kilos
One megadose of 2CB = 20 kilos
One megadose of MDMA = 100 kilos
One megadose of mescaline = 0.33 ton
One megadose of mushrooms = 3.3 ton

To take care of the needs of the world's psychedelic community of 2015 perhaps a gigadose might be required, the thousandfold of the above.

As you can see the logistic problems of fueling the psychedelic community through drug synthesis are overwhelming, and this explainsd while even with drugs as potent as LSD there still are large gaps in the supply chain.

But - these are the needs of the world today, I hope its useful or at least interesting to you :thumbup:


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OfflineChemiker
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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Asante]
    #6359541 - 12/11/06 10:06 PM (17 years, 5 months ago)

Since psychedelics are inherently no different than many other organic substances, the advances in psychedelic drug synthesis parallel the advances in organic chemistry in general. As with many biologically active molecules, an issue in synthesis is stereoselectivity. It is advantageous if one can produce a single enantiomer of the target molecule, because typically it is a single enantiomer that is active (or at least far more potent).

For example, some benzomorphans show activity as sigma or NMDA receptor antagonists (making them psychedelic dissociatives). One review emphasises the need for stereoselectivity, especially considering the fact that with this class of compounds, often one enantiomer is a psychedelic dissociative and the other is an opiate.

Palmer, D C. and Strauss, M J. Benzomorphans: Synthesis, Stereochemistry Reactions, and Spectroscopic Characterizations. Chemical Reviews. 77, pp. 1 - 36. (1977)

The Fischer indole synthesis is a well characterized reaction that can be used to generate a variety of indole backbone structures, which could be used in the synthesis of various substances bearing the indole backbone. The literature is full of examples of indole Fischer syntheses and of reviews of the mechanism.

To my knowledge, 8 different syntheses of lysergic acid have been published. I have three of them, I believe:

(1) Moldval, I. et al. Enantioefficient Synthesis of a-Ergocryptine: First Direct Synthesis of (+)-Lysergic Acid. Journal of Organic Chemistry. 69, pp. 5993 - 6000. (2004)

(2) Kornfeld, E C. The Total Synthesis of Lysergic Acid. 78, pp. 3087 - 3114. (1956)

(3) Hendrickson, J B. and Wang, J. A New Synthesis of Lysergic Acid. Organic Letters. 6, pp. 3 - 5. (2004)

I know that the biosynthetic pathway for the production of ergot alkaloids is well mapped and I imagine that one day psychedelics could be manufactured using biotechnology. This involves utilizing appropriate proteins produced by expression of their genes in expression vectors. Utilizing biotechnology would definitely help with the issues of stereoselectivity and would reduce impurities.

One area I would like to learn more about is the synthesis of THC and the psychoactivity and synthesis of THC deriviatives.

Personally, I attach little to no importance to the world's supply of psychedelic drugs and see no evidence that the widescale availability of psychedelic drugs in recreational* settings has a positive or negative impact on humanity. The only importance I attach with it is that I believe that people should have the choice to use psychedelic drugs if they feel like and I believe that research with these substances should be opened up.

* You can replace "recreational" with "mystical", "shamanic", "spiritual", "nonmedical", etc. here. I still don't believe that these drugs do the world any good. If evidence were available that showed otherwise, then I'd gladly change my mind. I think much of my look on psychedelic drugs is well reflected by Huston Smith's book, Cleansing the Doors of Perception. Being a chemist with an interest in psychedelic drugs means that I do have an interest in their synthesis and in helping spread accurate information about these drugs.

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Invisiblekake
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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Chemiker]
    #6359583 - 12/11/06 10:22 PM (17 years, 5 months ago)

I hate to advocate violence and blackmale, but the mafia always seemed to get its way. Why not set up some factories, and ... "protect" them? It's not exactly the good shephard's way of doing things, but then again, neither is dropping bombs on Baghdad, which the government gets away with.


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InvisibleAsante
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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: kake]
    #6362751 - 12/12/06 06:30 PM (17 years, 5 months ago)

Mafia?! :eek:

Personally I think its more important if the problems were explored from all angles, such as development of novel synthesis pathways using nonsuspect precursors, like so:




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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Asante]
    #6362821 - 12/12/06 06:50 PM (17 years, 5 months ago)

I like the novel approach, Wiccan_Seeker. I'm not a professional chemist, but I would just like to add this as a potentially novel idea:

From TIHKAL under 4-HO-DET:
Quote:


"Some fascinating studies have been done in Germany where the metabolically active mycelium of some Psilocybe species have been administered diethyltryptamine as a potential diet component. Normally, this mushroom species dutifully converts N,N-dimethyltryptamine (DMT) to psilocin, by introducing a 4-hydroxyl group into the molecule by something that is probably called an indole 4-hydroxylase by the biochemists. You put DMT in, and you get 4-hydroxy-DMT out, and this is psilocin. Maybe if you put Mickey Mouse in, you would get 4-hydroxy-Mickey Mouse out. It is as if the mushroom psyche didn't really care what it was working with, it was simply compelled to do its sacred duty to 4-hydroxylate any tryptamine it came across. It was observed that if you put N,N-diethyltryptamine (DET, not a material found in nature) into the growing process, the dutiful and ignorant enzymes would hydroxylate it to 4-hydroxy-N,N-diethyltryptamine (4-HO-DET) a potent drug also not known in nature. This is the title drug of this commentary. What a beautiful burr to thrust into the natural versus synthetic controversy. If a plant (a mushroom mycelium in this case) is given a man-made chemical, and this plant converts it, using its natural capabilities, into a product that had never before been known in nature, is that product natural? What is natural? This is the stuff of many long and pointless essays."





Just imagine "cloning" certain drugs in this manner....

Quote source:
http://www.erowid.org/library/books_online/tihkal/tihkal16.shtml#food


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InvisibleAsante
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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Chemiker]
    #6362837 - 12/12/06 06:55 PM (17 years, 5 months ago)

Quote:

The Fischer indole synthesis is a well characterized reaction that can be used to generate a variety of indole backbone structures, which could be used in the synthesis of various substances bearing the indole backbone. The literature is full of examples of indole Fischer syntheses and of reviews of the mechanism.





Indeed, the phenylhydrazones are readily formed and open the doorway to all sorts of indole compounds.

To grab acetaminophen by the tail again :wink: you could react that with a nitrite to form the N-nitroso compound, lightly reduce this, and then hydrolyze to yield 4-hydroxy-phenylhydrazine, which with acetaldehyde gives 5-hydroxyindole, which one might convert to 5-methoxyindole, opening the door to 5-MeO tryptamine goodness.

Quote:

For example, some benzomorphans show activity as sigma or NMDA receptor antagonists (making them psychedelic dissociatives). One review emphasises the need for stereoselectivity, especially considering the fact that with this class of compounds, often one enantiomer is a psychedelic dissociative and the other is an opiate.




Benzomorphans require quite some chemistry, and unusual precursors. Might it not be better to develop a phencyclidine analog that is closer to Ketamine, yet easier to synthesize and with higher potency?

Too bad you're not convinced of the beneficial effects of entheogens for humanity. :frown:


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InvisibleAsante
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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Darkcloud]
    #6365662 - 12/13/06 11:11 AM (17 years, 5 months ago)

Darkcloud, the problem with this wonderful approach is that if you feed Cubies DPT they will indeed contain 4-HO-DPT, but because the enzyme system is intact there will be a minor content of Psilocin, which would still make the operation illegal.

The same goes with the ALD synthesis. Basically ALD is LSD with an acetyl group attached to the nitrogen of the indole. Part of the conviction was that because LSD was used to make ALD, it was still a clandestine lab operation.

If you could modify the mushroom so it produces 4-HO-tryptamine from substrate, you can chemically substitute that to your hearts desire and because the genes are altered it is not a Cubie anymore, so it would all be legal.


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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Asante]
    #6367702 - 12/13/06 08:19 PM (17 years, 5 months ago)

This isn't a subject I'm familiar with at all, but it's really fascinating to read the opinions of people who have put serious intellectual thought into this. Here is one question i have for those who might have any idea: why has there not been chemical analogues made from the psychoactive components of salvia, the same way we've seen chemical analogues from tryptamines and phenethylamines produced?


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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: MisterKite]
    #6367962 - 12/13/06 09:08 PM (17 years, 5 months ago)

Part of it would just be a funding issue. Making new chemicals costs money and unless you are interested enough in putting your own money into that kind of thing you've got to get money from somewhere else. Personally, I don't think too many organizations are going to fund that kind of thing (what's the application? what's the reason? What's the benefit? - you're asking people for their money, so you've got to be pretty convincing that the research is important).

I'm not familiar with the structure of the active substances in Salvia, but some chemicals are really damn expensive to synthesize. The most expensive I've ever heard of is a chemical found in seaweed. It can either be extracted, at a ratio of something like one gram of this compound per 10000 kg of seaweed or you can synthesize in a 72 step process. The going rate for this compound, last I heard, was $2.3 million per gram.

Actually, I'm curious if you're actually sure that no analogues have been prepared? It's possible that some have but that nobody was using them in assays for psychoactivity.

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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Chemiker]
    #6367978 - 12/13/06 09:11 PM (17 years, 5 months ago)

By the way Wiccan,

on Friday I'm going to do a little research into that Fries rearrangement and try to answer two questions:

(1) Can it be done without a Lewis acid catalyst? (and if not, can it be done with an easily obtainable catalyst?)
(2) What regiochemistry is preferred in this case?

If I have time I'm going to search the literature for precedents for the other aspects of your reaction. In theory, what you've proposed and we've discussed is workable, but I'd like to actually see if I could find specific reaction conditions if any of these reactions have already been carried out.

I only can get print access, but this article may be of use:

Martin, R. USES OF THE FRIES REARRANGEMENT FOR THE PREPARATION OF HYDROXYARYLKETONES - A REVIEW. Organic Preparations and Procedures International. 24, pp. 369 - 435. (1992)

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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Chemiker]
    #6374323 - 12/15/06 02:15 PM (17 years, 5 months ago)

So I looked for the rearrangement but could not find it exactly. The closest I could find started out with acetominaphen (I think, maybe it laked the OH substituent) and rearrangement to the ortho position was preferred. This was matched by an alkylation at the other otho position by an arm of a substituted phenly group. The result was three six membered rings fused together (14 carbons making up the ringzs): the two outer rings were pheny groups. The bridging carbons on the inner rings were carbonyl carbons (ketones, as in the target you wanted). I don't have the reference handy off hand, but I can get it for you.

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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Asante]
    #6381551 - 12/17/06 10:25 PM (17 years, 5 months ago)

How do you propose to complete the first reaction in anything greater than like 5% yield and then separate out all the other 95% of crap?

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InvisibleEgo Death
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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Asante]
    #6382435 - 12/18/06 08:34 AM (17 years, 5 months ago)

What plants could be used for redox reactions?

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InvisibleAsante
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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: ChuangTzu]
    #6383093 - 12/18/06 12:53 PM (17 years, 5 months ago)

Quote:

How do you propose to complete the first reaction in anything greater than like 5% yield and then separate out all the other 95% of crap?





You tell me, help us out here!

Once the ayl ketone is formed it has a deactivating effect so another acetyl group won't add to it.

But what kind of side reactions do you see taking over the rearrangement of acetaminophen then? Criticism is easy, it would be great if we could work towards solutions together. You probably see the use in a reaction scheme that would convert acetaminophen into a 2,5-disubstituted acetophenone, so why not look into it to see how it can be made to work?


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Edited by Asante (12/18/06 12:56 PM)

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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Asante]
    #8337753 - 04/28/08 02:14 PM (16 years, 24 days ago)

I know this thread is old but I thought it was a great read.  Personally, I think it would be awesome to see organic and biochemistry evolve to the point to where we could purposely develop new drugs.

In theory we just need to develop chemicals that bind to the active sites on the axon terminals and dendritic spines within neuronal synapses, mimicking neurotransmitters such as dopamine, serotonin, epinephrine, etc.

Science isn't really far enough along to manufacture a large number of patents for new psychoactive drugs.  LSD was found as a hallucinogen on accident, and mushrooms are natural. Cocaine is concentrated and natural, meth was an accident, pot is natural, i don't know the history of X to well, but it's all beside the point.

If we can find a way to make synthetic neurotransmitters and then alter them so they are directed to different parts of the brain (sensory is the area we are concerned with, the optic tract would be a great point of interest! :smile: then we would be on our way to designing drugs with specific  highs.  Maybe you want that heroine high, but not as much drug seeking behavior...  then we find a drug that binds to opioid receptors, but doesn't involve any tracts routing to the nucleus accumbens (motivation), or the cingulate gyrus or other emotional control centers.

Unfortunately, this is distant technology.


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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Asante]
    #8338196 - 04/28/08 04:29 PM (16 years, 24 days ago)

It is my dream to find a route to D-LSD that is relatively simple and can be carried out by the average cook.

Unfortunately Organic Chemistry is not my forte.. its just not as interesting as Physical / Inorganic / Physics :grin:

I am schooling myself on the matter though, and I have an idea for a website devoted to this type of discussion, away from the prying eyes of the law (i.e. invite only / SSL / PGP encrypted pages etc).

I have my own hosted server (sat right next to me) I just need to recruit some people for the cause :grin:


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Invisibleleoside
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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Cepheus]
    #8339559 - 04/28/08 09:28 PM (16 years, 24 days ago)

I wonder how active this molecule would be.

D-Tryptophan cyclized:

[image][/image]

N-methylate at will


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InvisibleAsante
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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: leoside]
    #8340079 - 04/28/08 11:14 PM (16 years, 24 days ago)

Actually the phenylalkyl is a phenyl ketone group. Then you have an aminoketone, which tends to get messy. The amione must be converted first.

But how will you make the carboxylic acid grab the phenyl and not the adjacent spot on the pyrrole ring?

Your drawn compound with two N-methyls likely would be entheogenic, probably orally.


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Invisibleleoside
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Re: Psychedelic Drug Synthesis -- an uncensored discussion of its past, present and future [Re: Asante]
    #8340101 - 04/28/08 11:17 PM (16 years, 24 days ago)

N-protect, convert the carboxylic acid to an acid chloride and carry out a friedel crafts.

I believe a similar reaction has been carried out in another LSD synthesis

Indoles are susceptible to electrophillic attack at position 3 and 4. 2 Isn't seen as much, apparently.


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