The Vespiary

The Hive => Tryptamine Chemistry => Topic started by: Lilienthal on May 31, 2000, 06:22:00 PM

Title: New tryptamine literature
Post by: Lilienthal on May 31, 2000, 06:22:00 PM
This new and forever growing thread is devoted to new literature relevant for tryptamine / lysergamide chemistry. Let's discuss these papers in separate threads for a better overview.

Heterocycles 51, 1131 1999 H. Sakagami, K. Ogasawara: A new synthesis of psilocin. A seven-step-low-over-all-yield-very-complicated synthesis.

J. Chem. Soc. Perk I 1045 2000 G. W. Gribble: Recent developments in indole ring synthesis - methodology and applications. Great review articel covering the whole modern indole chemistry. Someone (I forgot who) already mentioned this article at the old board.

Title: Re: New tryptamine literature
Post by: Rhodium on May 31, 2000, 07:10:00 PM
Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin
D. E. Nichols, S. Frescas
Synthesis No 6, p 935-938 (1999)

Four steps from 4-benzyloxyindole in 79% overall yield. Also includes an improved synthesis of psilocybin from psilocin (hard work, 46% yield). (

Title: Re: New tryptamine literature
Post by: psyloxy on May 31, 2000, 08:13:00 PM
What about the book 'LSD 25 and Tryptamine Syntheses' by O. Snow ? I didn't like his book on amphetamines much but the reference section was good.


Title: Re: New tryptamine literature
Post by: Rhodium on June 11, 2000, 05:22:00 PM
The new Psilocin/Psilocybin/4-acetoxy-DMT synthesis by nichols is now available at my site (Thanks Omnipage 10, the only thing I had to correct was Et2O and CH2Cl2, which was interpreted as EzO and CHzCIz). ( (

Title: Re: New tryptamine literature
Post by: Tryptamine on July 06, 2015, 12:01:52 PM
What are the best routes to take DMT, DET, MET, DPT and add ACO-, HO-, PO- on the 4 position? I cannot find literature for each of these. I did not want to write all 12 out. Thanks.
Title: Re: New tryptamine literature
Post by: dopamine on July 06, 2015, 01:08:14 PM

This took like 3 seconds to google.  Im sure the rest are similarly easy to find (provided they exist)

4-Acetoxy-N,N-dimethyltryptamine5 fumarate (2)
In a 250 mL Parr hydrogenation bottle was placed 0.25 g of 10% palladium on charcoal followed by anhyd sodium acetate (1.50 g, 18 mmol). Benzene (50 mL) was added, followed by acetic anhydride (5 mL, 5.41 g, 5.32 mmol), and 4 (0.50 g, 1.7 mmol). The mixture was shaken under 60 psig of hydrogen for 4 h. After the uptake of hydrogen had ceased the hydrogenation bottle was removed from the apparatus, the mixture was diluted with THF (25 mL), and the catalyst was removed by filtration through a pad of Celite 545. The catalyst was washed repeatedly with isopropanol (3 x 50 mL). The washings and mother liquor were collected separately because of unreacted Ac2O in the filtrate. The mother liquor was concentrated under vacuum to about one half the original volume, then toluene (50 mL) was added. The solution was again concentrated by rotary evaporation. The isopropanol washes were combined with the residue and also concentrated. The residue was then dissolved in anhyd MeOH (50 mL). Fumaric acid (0.198 g, 1.7 mmol) was dissolved in MeOH (10 mL) and added to the stirred methanolic solution of the residue. After stirring for 10 minutes, toluene (50 mL) was added and the solution was concentrated to dryness by rotary evaporation. Absolute EtOH was added to the residue and a white precipitate of 2 fumarate (0.290 g, 0.8 mmol) formed and was collected by filtration. The filtrate was evaporated and the residue was dissolved in a minimum amount of MeOH. EtOAc was added and clear crystals began to form. After storing the solution in a freezer at -10°C, 0.170 g of additional product was collected for a total yield of 0.460 g (74.8%); mp 172-173°C.
Title: Re: New tryptamine literature
Post by: Tryptamine on July 06, 2015, 05:27:46 PM
Some are known in Tihkal.  Others have never been produced in literature. Also looking for ALZ, AL-LAZ, and 1P-LSZ. 
Title: Re: New tryptamine literature
Post by: Kykeon on July 06, 2015, 06:10:34 PM
The attached paper was kindly showed to me recently, it contains some good information.

It also contains a route to 4-OH-tryptamines: