I have tried to synthesize mescaline from 3,4,5-trimethoxybenzaldehyde via two different routes. Everything seemed to work well until the last step, yet no desired product was obtained. Does anyone have an idea of what might have gone wrong?
My route was in principle the following:
1) 3,4,5-trimethoxynitrostyrene from 3,4,5-tmba :
10 g of 3,4,5-tmba were disolved in an mixture of 16 ml of nitromethane in 74 ml of ethanol. The solution was cooled to 0 °C.
8.42 g of KOH were added slowly. The temperature was kept below 5 °C using an ice bath. After the mixture sat for 1 hour at 0 °C it was added to 300 ml of chilled 10 % HCL in Water. The temperature was kept below 10 °C. Yellow flakes of 3,4,5-tmns fell out of the solution and were filtered out after waiting 1 hour. The 3,4,5-tmns was only slightliy dried before it was used in the following reduction steps.
2.1) reduction method one: mescaline from 3,4,5-tmns via AlAmalgam :
about 10 g of 3,4,5-tmns were dumped into a large jar filled with 0.5 g of HgCl2 solved in 100 ml GAA, 150 ml IPA and 50 ml water.
20 g of shredded aluminum foil were added and the mixture was stirred using a magnetic stirbar. A violent reaction proceeded for about 10 minutes, the mixture was allowed to react for 5 hours afterwards. After the reaction was complete the grey sludge inside the jar was treated with a solution of 150 g KOH in 400 ml Water. The resulting orange IPA layer was seperated for subsequent workup. To obtain the mescaline hcl salt, the orange IPA layer was gassed with dry HCL gas. The gas was produced by heating a mixture of table salt and sodium bisulfate inside a testtube inside an oven. Upon introduction of the HCL gas white flakes of (what I assumed to be) Mescaline HCl fell out of the solution. After a while the solution turned from transparent orange to an deep opaque red. The fallout of white flakes stopped shortly after. The flakes where filtered and washed multiple times with IPA and chilled Acetone. The result were about 4 g of a white crystaline smellless substance. The substance was tested with Liebermann reagent. The color changed to a very very faint barely visible brown...The synthesis must have failed. But where? What is the white substance?
2.2) reduction method two: mescaline from 3,4,5-tmns via Zn/HCL
about 10 g of 3,4,5-tmns were added to a chilled solution of 300 ml 31% HCL and 200 ml IPA. The solution was cooled cooled using an ice bath and stirred using a magnetic stirrer. Zn was added at a rate of 1g per minute, a total of 50g was added. The temperature was kept below 10 ° C. After the addition of the Zn was complete, the mixture was allowed to sit for 5 hours. 393 g KOH in 800 ml Water were slowly added to the mixture, the temperature was kept below 30 °C. After another 5 hours of standing three distinct layers seperated: A white solid layer at the bottom, a slightly yellow aqueous layer in the middle and a orange IPA layer at the top. The orange IPA layer was seperated and treated with HCL gas simmilarly as in 2.1). The resulting solid was filtered out. It was white with a slight grey tint and a strong amine smell. When tested with Liebermann reagent the color changed to a deep brown/black. The sample fizzled when it came in contact with the reagent. The substance had a slightly salty taste.
1 mg, 10 mg, 100 mg and 350 mg of the substance were consumed (with one week breake inbetween for tolerance) but no psychedelic effects were noticed. On 350 mg after about 3 hours an energetic rush, equivalent to a cup of strong coffee was encountered. It seems this synthesis also failed. Is something wrong with the workup?
Ill appreciate any type of help! Thanks!
My route was in principle the following:
1) 3,4,5-trimethoxynitrostyrene from 3,4,5-tmba :
10 g of 3,4,5-tmba were disolved in an mixture of 16 ml of nitromethane in 74 ml of ethanol. The solution was cooled to 0 °C.
8.42 g of KOH were added slowly. The temperature was kept below 5 °C using an ice bath. After the mixture sat for 1 hour at 0 °C it was added to 300 ml of chilled 10 % HCL in Water. The temperature was kept below 10 °C. Yellow flakes of 3,4,5-tmns fell out of the solution and were filtered out after waiting 1 hour. The 3,4,5-tmns was only slightliy dried before it was used in the following reduction steps.
2.1) reduction method one: mescaline from 3,4,5-tmns via AlAmalgam :
about 10 g of 3,4,5-tmns were dumped into a large jar filled with 0.5 g of HgCl2 solved in 100 ml GAA, 150 ml IPA and 50 ml water.
20 g of shredded aluminum foil were added and the mixture was stirred using a magnetic stirbar. A violent reaction proceeded for about 10 minutes, the mixture was allowed to react for 5 hours afterwards. After the reaction was complete the grey sludge inside the jar was treated with a solution of 150 g KOH in 400 ml Water. The resulting orange IPA layer was seperated for subsequent workup. To obtain the mescaline hcl salt, the orange IPA layer was gassed with dry HCL gas. The gas was produced by heating a mixture of table salt and sodium bisulfate inside a testtube inside an oven. Upon introduction of the HCL gas white flakes of (what I assumed to be) Mescaline HCl fell out of the solution. After a while the solution turned from transparent orange to an deep opaque red. The fallout of white flakes stopped shortly after. The flakes where filtered and washed multiple times with IPA and chilled Acetone. The result were about 4 g of a white crystaline smellless substance. The substance was tested with Liebermann reagent. The color changed to a very very faint barely visible brown...The synthesis must have failed. But where? What is the white substance?
2.2) reduction method two: mescaline from 3,4,5-tmns via Zn/HCL
about 10 g of 3,4,5-tmns were added to a chilled solution of 300 ml 31% HCL and 200 ml IPA. The solution was cooled cooled using an ice bath and stirred using a magnetic stirrer. Zn was added at a rate of 1g per minute, a total of 50g was added. The temperature was kept below 10 ° C. After the addition of the Zn was complete, the mixture was allowed to sit for 5 hours. 393 g KOH in 800 ml Water were slowly added to the mixture, the temperature was kept below 30 °C. After another 5 hours of standing three distinct layers seperated: A white solid layer at the bottom, a slightly yellow aqueous layer in the middle and a orange IPA layer at the top. The orange IPA layer was seperated and treated with HCL gas simmilarly as in 2.1). The resulting solid was filtered out. It was white with a slight grey tint and a strong amine smell. When tested with Liebermann reagent the color changed to a deep brown/black. The sample fizzled when it came in contact with the reagent. The substance had a slightly salty taste.
1 mg, 10 mg, 100 mg and 350 mg of the substance were consumed (with one week breake inbetween for tolerance) but no psychedelic effects were noticed. On 350 mg after about 3 hours an energetic rush, equivalent to a cup of strong coffee was encountered. It seems this synthesis also failed. Is something wrong with the workup?
Ill appreciate any type of help! Thanks!
