N’ N diethyl serotonin synthesis:

N’ N diethyl serotonin is a really powerful hallucinogenic compound. The ED is 4-8mg. This compound is similar to psilocin/psilocybin/DET/trypamines. It is a really effective hallucinogen.

My synthesis is based on the Fischer indole synthesis. But instead of phenyl hydrazine, I use para hydroxyl phenyl hydrazine as you can see on the drawing. The other compound, is the N’ N diethyl 4 amino butyric aldehyde.

So let’s see the first compound, the para hydroxyl phenyl hydrazine. The synthesis of this compound is started from phenol.
A:
-A phenol solution is nitrated with 30% nitric acid at 0 Celsius.
-The solution is distilled. With the water, the ortho isomer distills out and the para isomer remains at the bottom of the breaker.
B:
-We make para phenol nitrite by adding 10-15% H2SO4 to the solution of sodium-nitrite and phenol at 5 Celsius.
-The solution should be neutralized with sodium-carbonate. And the water should be distilled out.
-The white powder what we obtained (mixture of para phenol nitrite and sodium-sulfate) should be added slowly to 40 Celsius hot 23% nitric acid.
-The para nitro phenol is obtained by distillation and recrystallization from hot water. (it is highly soluble in hot water, but almost insoluble in cold water).
C:
-Iron powder is added to a concentrate para nitro phenol solution and hydrochloric acid is added in 2 ml portions. The reaction is cooled by ice to 20-25 Celsius. After this the aminophenol filtered and washed with cold water. .
D:
-The aminophenol is added to a sodium-nitrite solution and it is diazotized by adding 10% HCl to the mixture. The reaction is cooled by ice to 5 Celsius.
E:
-To the previous solution sodium sulfite and some sodium-hydroxide is added. This will reduce the diazophenol to phenyl hydrazine.
-You should add some chloroform or ether to get the hydroxyl phenyl hydrazine out from the reaction mixture.
-The pure product is sensitive to air. It should be stored in its solution with ether or chloroform in a dark glass bottle at a dark and old place. It should be prepared before you use it. It will decompose if you store it long.

Let’s see the second precursor, the N’ N diethyl 4 amino butyric aldehyde:

A:
-At first we should make 4 nitro butyric acid what can be produced adding to boiling butyric acid  N2O4 or NO2. The second method is “normal” nitration with concentrated nitric and some P4O10 for the better yield. The not reacted butyric acid is distilled off. (beware, extremely bad smell:-D).
B:
The nitro butyric acid should be hydrogenised by hydrogen gas and palladium on carbon/platinum black/raney nickel. The obtained gamma amino butyric acid can be easily oxidized on air, so you should filter it (to get out the palladium/platinum/nickel).
C:
The filtered gamma amino butyric acid is added to ethanol and phosphoric acid and boiled to make the ethyl ester. When the reaction is ready (approx 20 minute boiling) you should add some ether to get out the amino butyric acid ethyl ester. This step is not needed, just if you make the ethyl ester, than you will need less ethyl bromide at the next step.
D:
The mixture from the previous reaction is boiled, to get the remaining ethanol out. It is cooled down to 10 Celsius and the ethyl bromide is added to it slowly. A lot of hydrogen bromide will evolve, so don’t breathe it in.
E:
The product is added to a calcium hydroxide solution and boiled. Some ethanol will distill out. Now we got the calcium salt of the N’ N diethyl butyric acid. And some calcium bromide.
F:
We should mix the calcium salt of the N’ N diethyl butyric acid with calcium formate in a stainless steel or glass retort. It should be heated to 350-500 Celsius. At this temperature the calcium formate will reduce the N’ N diethyl butyric acid calcium salt to N’ N diethyl butyric aldehyde. The N’ N diethyl butyric aldehyde should be collected in a dark glass and should be stored at a cold, dark place until we use it. From this reaction di(N’ N diethyl butyric) ketone will be also produced, so we should vacuum distill this product one time (N’ N diethyl butyric aldehyde has much lower boiling pont). 

And at last, the serotonin synthesis:

We should mix this two chemicals with 10% hydrochloric acid and boil it for a while. The obtained compound will be a crystalline solid: the N’ N diethyl seratonin.
An other way: the two chemicals should be mixed with 4x zinc chloride and heated to 180 Celsius for 10-15 minutes. Instead of the zinc-chloride heating high boiling point solvents can be also used: glycol, tetraline or methyl naphthalene can be also used. The reaction is completed when no more ammonia evolves.

So, this is the draft… I hope I can make it soon.

If you have any idea or any information from the reactions, compounds above than write it. Thanks!

-Evilblaze

I know that 5-hydroxytryptophan can be easily decarboxylezed to seratonin, but the only problem is the 5-hydroxytryptophan. I know, that it is sold in the US, but at us, we can not buy a compound like this, so the synthesis is our only choice.

As I know that in US the 5-hydroxytryptophan is sold in 100mg tablets. It can be easily extracted from it and after that the seratonin synthesis is peace of cake.

The synthesis of 5-hydroxytryptophan can be also done, but it is not so easy. The -OH on the benzene ring is not easy. At first I just wanted to make seratonin from indole acetic acid or normal indole, but the problem was that if I want to put an -OH on the benzene, than it wont go there. It would go on next to the nitrogen. An other method would be, that I put a MgI on the nitrogen of the indole acetic acid and than the OH would go to the 5 position, but than a big percent of my indole would decompose because of the halogenization and the reaction with NaOH. So I just chose this version. The phenol is cheap, the butyric acid is also cheap, the other reagents are not so expensive. But if I want to make seratonin from indole compounds than it would be expensive, 100g of indole 3 acetic acid is 250 euro....

The 8mg is the calculated ED. I got the binding lengths between the tryptamine analogs and the h5-HT receptors. I got info from 50 tryptamine analog.

The optimal is the normal seratonin with 10nM. The DMT what is used as drug is 300 nM, the synthetic diethyl tryptamine is 990 nM. The normal tryptamine is 500 nM. The dimethyl seratonin is 9 nM and the diethyl compound is 36 nM. So as you can see, it is really effective.

The dimethyl and the normal seratonin can't be used as drugs, because it decompose too fast in the human body. But if you use the ethyl, than it wont decompose:-D

From dimethyl seratonine you can read on wikipedia: http://en.wikipedia.org/wiki/Bufotenin#Effects_in_Humans

The monoamine oxidase named enzyme degrades DMT, N N' dimethyl seratonin to an inactive compound before it could be absorbed, but if the alkane chains on the nitrogen are longer than 1 carbon, than this enzyme could not degrade the drug.

And the Psilocybin..... I think the phosphoric acid prevents the molecule from the enzyme. I have no other idea.

The EtBr part of this was originally thought to made with pyridine as a solvent. And in that case the ethylazition could be make properly. The HBr would go on the pyridine and no problem would occur.

The H3PO4 part wasn't in the original synthesis. On of my friends said, that it could be cheaper if we would make the ethyl ester with normal method from alcohol, and than we need less EtBr. The idea was not bad, the only problem is what you wrote with the lactame.

The separation of the 4 nitro and other nitro BA is not so hard. With HNO2 they will give nitrol acids and pseudonitrol acids ( I hope, I translated it correctly). The 4 nitro butyrlic acid with HNO2 gives 4 nitro 3 nitrite burtyric acid what is soluble in bases, while the 2 and 3 nitro burtyric acids nitrites are not soluble in bases. So, no problem. The only problem is to turn back the nitrites to the "normal" compound, but I will find this out in time I think....
And if it can't be separated, than also no problem, because the other compounds are inactive hallucinogens.

And the topics original name was "N' N diethyl serotonin synthesis draft", but one of the moderators edited it.....  My fault - Enkidu

Synthesis of Indoleacetic Acid from Glutamic Acid and a Proposed Mechanism for the Conversion
Sidney W. Fox, Milon W. Bullock
J. Am. Chem. Soc. 1951, 73 (6), pp 2754–2755
DOI: 10.1021/ja01150a094

Abstract
An economical method for converting glutamic acid to indoleacetic acid, through the intermediate succinaldehydic acid phenylhydrazone, has been developed. a-Ketoglutaric acid has been found as a by-product in the preparation of the succinaldehydic acid. For the decomposition of the intermediate a-N-chloroaminoglutaric acid there is a proposed mechanism which explains the formation of all the products isolated from the reaction mixture

That paper has been provided by Java on page 4 of the Reference Request topic in the appropriate sub-forum (not too hard to find, follow the link, top of the page) - careful (ie. mild both in terms of temp & acid strength) hydrolysis of paracetamol will give you p-hydroxyaniline, which can be utilized to form the p-hydroxyphenylhydrazine and thus the p-hydroxyphenylhydrazone of succinaldehydic acid.

Fuck N,N-dimethyl/diethyl - if you have the opportunity to do the ground up synthesis, go for gold - N,N-diisopropyl-5-MeO-tryptamine (aka Foxy) sounds nice

PS For those looking to go for broke from the get-go, the relevant amino acid(s) you need for direct synthesis (albeit the yields would probably suck) of Tryptamine from the appropriate phenylhydrazide of a Strecker degradation product (in this case, 4-aminobutyraldehyde) would be Ornithine (a non-essential amino acid - so harder to acquire - but which is basically Glutamic acid with an amine on the end instead of a carboxylic acid) which is also available via hydrolysis of Arginine (a semi-essential amino acid - so piss easy to acquire - I have attached a paper on the hydrolysis thereof).

The use of 4-aminobutyraldehyde is not exactly a new idea, it is mentioned here and also here (amongst hundreds of other ref's)... Presumptively, the required Strecker Degradation would be essentially the same as other Strecker Deg's (like the one provided on this forum by Java) and the use of a phenylhydrazide to isolate the aldehyde therefrom as the hydrazone is hardly a novel idea.

PPS I even attached the cited article - just to save you having to look around too much

5-Methoxy-Diethyltryptamine has been reported as being a "nightmare" psychedelic.  Unpleasant.  If true, that is too bad.  Easy to make, via over the counter (in US) Melatonin.  Check Tikal.

"Dimethylethanolamine is available in the US (as I heard). Just add some hot CuO to this, filter it and add the N’ N dimethyl 4 amino butyric aldehyde to the para hydroxyl phenyl hydrazine in a high boiling point solvent to obtain the dimethyl seratonin."

Do you have a reference for an easy synthesis of  4-N,N-Dimethylamino-Butyric Aldehyde?