D-LAME Synthesis

[Octopusssss]

Hello Bee friends

I am interested in informations about D-LAME synthesis (D-Lysercic Amide Methyl Ester). Its quite cheap in china and i would like to know if its product made from L-tryptophan or maybe its made from ergot biosynthesis in liquid cultures?
I will be very grateful for any information on this topic.

Thank You

 

[Rabidreject]

I think you’ll struggle to find free info regarding this stuff. It’s VERY lucrative business and any posts iv seen on here have had MINIMAL info on as I know someone is selling the total synth from that to LSD-25 for over €1000….its just been my experience. I asked the same question on another forum a while back.
Don’t get me wrong I hope someone explains coz it’s interesting as f. But still…

 

[The-Hive]

Dm
DM me

 

[Octopusssss]

In literature the most interesting for me is this road:

https://www.erowid.org/archive/rhodium/pdf/ergot-tryptophan.pdf

Synthesis of Ergot Alkaloids from Tryptophan

Rebek, Jr.,* D. F. Tai, and Y.-K. Shue - 1984

Procedure is in Experiment Section and i think nowadays we are able to cut the corners and maybe gain goal in less steps...

Have a good day

 

[Sassypants]

Ergot Alkaloids and Related Compounds
edited by B. Berde, H.O. Schild is a good read

 

[Octopusssss]

Simple road from 2004 is:

A New Synthesis of Lysergic Acid - [www.rhodium.ws]

Starting material is 3-methoxycarbonylindole with less steps - if there is easy and cheap 3-methoxycarbonylindole synthesis - please let me know

 

[Tsigger]

Compared to LSD, how strong is d-lame? What is its dosage?

 

[Sassypants]

Nobody cares,

Methyl esters are cleaved by base or acid hydrolsis. Leaving LA

Add a coupling reagent, convert Deet into diethylamine or just buy it and done.

 

[Sassypants]

An asymmetric synthesis of (+)-lysergic acid methyl ester was accomplished through construction of the tetracyclic ergoline skeleton by double cyclization consisting of intramolecular aromatic amination and Heck reaction.

Synthesis of Lysergic Acid Methyl Ester via the Double Cyclization Strategy | 10.1055/s-0028-1087948_Sci-hub

www.pismin.com

For the more adventrous 9, 10- Dihydrolysergic acid has been obtained from lysergol with overall 40% yield

 

[Sassypants]

D-lame is

CAS Number

4579-64-0

IUPAC name Methyl 6-methyl-9,10-didehydroergoline-8β-carboxylate

Dihydrolysergic Acid | CAS No- 5878-43-3​

 

[Sassypants]

A scalable new approach for the preparation of N-6-demethylated 9,10-dihydrolysergic acid methyl ester using 2,2,2-trichloroethyl chloroformate was developed. A key discovery that enabled the efficient and industrial-scalable process is linked to the rigorous extrusion of water in the reaction system and application of an organic catalyst such as 4-(N,N-dimethylamino)pyridine (DMAP) instead of the alkali metal bicarbonate additives. Namely, in the previously known process, the concomitant presence of bicarbonates and traces of water triggers side reaction cycles that produce and accumulate hydrochloric acid and water. The former slows down the reaction. Moreover, these cycles cause the formation of multiple carbonate and alcohol-type side products to a significant extent that provide a low-quality N-6-demethylated product. All of these shortcomings are circumvented by the application of DMAP as a catalyst and the use of a reaction medium free of water. This approach allows operation on an industrial scale (51 kg batch) with higher yields, shorter reaction times, and improved product quality.

 

[HerrHaber]

is that dihydronorlysergic acid?

 

[HerrHaber]

As far as I know dihydroLSD is somewhat less potent

 

[Sassypants]

I always thought dihydro and dibromo compounds are easily manipulated as precoursers but aren't often talked about...

For example ... I've always had a dream of finding or using the dibromo compound of mdp2p and doing catalytic hydrogenation with borohydrides ... I could be wrong but it should yield target compound.from my dreams and talks with others

 

[HerrHaber]

Dihydrolysergic would be much more difficult to oxidise back with specificity and for brominated analogs I thought of 2-Bromo which in turn could be dehalogenated with more precision via Grignard followed by hydrolysis, I remember someone claiming to do this with the inactive 2-Br-LSD.

 

[Sassypants]

I had a similar idea with what you were thinking. But my chemistry less sound. Def thought or heard about that though.

 

[Sassypants]

Eitherway the yellow brick road is always evolving so to speak

IDK why a friend of mine did this or maybe I DO know why ..q

After 4 semesters in the organic chemistry lab, I made not one, but TWO novel compounds this summer. I'm overjoyed! One is the tetra-hydro intermediate of the following compound, and the other is 1-(3-methoxyphenyl-5-methyl-4-isoxazolyl)-β-carboline intended final product.


I basically told why myself why do I kinda know what that looks like and

That it’s a beta carboline with an isoxazole R group. The R group is not a normal isoxazole though. I’m using the Pictet Spengler synthesis with trypamine and this isoxazole carboxaldehyde

Synthesis for novel B-carboline ring systems...

And all I thought was why do someone I know. Doing something soooo uhh ad hoc jacent to something I known. Sadly my nomenclature/IPUAC sucks and need it drawn out XD

 

[Sassypants]

Sadly I've spent more times developing MDMA and even more boring meth and it's analogs paths then LSD.. as my education is limited not bad/horrible. But... I've def been try to branch out to Lysergic alkaloids and come up with other ideas that aren't so LAME AND over used. But just as elegant so to speak with similar esters.

 

[Sassypants]

I've always been told the REAL gold is in Perdue patents with ergot alkaloids or similar compounds.

 

[Sassypants]

So I'm sure if I dig in academia I could like most people come up with something unique