DMT synthesis?

Synthesis involves formaldehyde and dcm, chemicals that are out of reach of most of us.

https://www.erowid.org/archive/rhodium/chemistry/tryptamine2dmt.html

Interesting read nonetheless though.

FROM TIHKAL- ALEX SHULGIN RIP: #6. DMT TRYPTAMINE, N,N-DIMETHYL; INDOLE, 3-[2-(DIMETHYLAMINO)ETHYL]; N,N-DIMETHYLTRYPTAMINE; 3-[2-(DIMETHYLAMINO)ETHYL]INDOLE; DESOXYBUFOTENINE; NIGERINE

SYNTHESIS : (from N,N,N-trimethyltryptammonium iodide, dimethyltryptamine methiodide, DMT·CH3I): This quaternary salt is prepared from tryptamine and methyl iodide. To a stirred solution of 3 g tryptamine in 30 mL IPA there was added 10 g methyl iodide. Cream-colored solids appeared immediately and, after 12 h stirring at room temperature, these were removed by filtration, washed twice with IPA and warm isopropanol, and air dried to constant weight. There was thus obtained 1.81 g N,N,N-trimethyltryptammonium iodide. Recrystallization of an analytical sample using acetonitrile gave a white crystalline product with a mp of 210-211 °C. IR (in cm-1): 767, 919, 953, 978, 1105, with a sharp stretch at 3400. In principle, DMT is contained in the filtrate along with NMT and tryptamine itself. The tryptamine can be removed based on its ether insolubility and the NMT by its conversion to the benzamide with acetic anhydride or benzoyl chloride. The remaining basic material is largely DMT which can be further purified as the picrate salt. The yield is minuscule, and better results are obtained by the demethylation of this salt.

The demethylation of the iodide salt: Under an inert atmosphere, a solution of 0.40 g N,N,N-trimethyltryptammonium iodide in 5 mL THF was treated with 1.5 mL of 1M LiEt3BH in THF and held at reflux temperature for 9 h. After cooling, the mixture was acidified with dilute HCl and the THF removed under vacuum. The residue was suspended in dilute NaOH and extracted with Et2O. The extracts were pooled, and the solvent removed under vacuum to provide a residue of 0.12 g N,N-dimethyltryptamine (DMT) as a crystalline solid, with a mp of 57-59 °C. IR (in cm-1): 732, 740, 811, 859, 1011, 1037, 1110, 1171. The MS is discussed below.

The demethylation of the chloride salt: A hot aqueous solution of N,N,N-trimethyltryptammonium iodide was treated with an excess of freshly precipitated AgCl, and all was boiled gently for 15 min. The mixed silver halides were removed by filtration, and the filtrate stripped of H2O as rapidly as possible. To the residue there was added a small amount of MeOH follow by acetone until the crystallization of N,N,N-trimethyltryptammonium chloride was complete. It had a mp of 193 °C (80%), and it is considerably more water soluble than the starting iodide. This salt was pyrolysed under hard vacuum and the residue distilled. This distillate was dissolved in a small amount of methanol and acidified with dilute nitric acid. A small amount of insoluble material was removed by filtration, the aqueous phase washed with CHCl3, made basic with aqueous NaOH, and extracted with CHCl3. The solvent was removed under vacuum, and the residue treated with a hot solution of picric acid. This was decanted from a little insoluble material, and slowly cooled to provide the picrate of DMT as yellow needles with a mp of 167 °C. An aqueous suspension of this picrate was made basic with an excess of aqueous NaOH, extracted with Et2O, and the solvent removed under vacuum to provide a pale yellow residue that crystallized. This was pressed on a porous plate and washed with petroleum ether to give N,N-dimethyltryptamine (DMT) as an off-white solid with a mp of 47 °C.

The demethylation of the thiophenolate salt: A suspension of 2.5 g N,N,N-trimethyltryptammonium iodide in 25 mL MeOH was brought into solution by heating, and treated with 1.0 g Ag2O. The mixture was heated for 10 min on the steam bath, the solids removed by filtration and washed with an additional 20 mL MeOH. The methanol solutions were treated with 1.0 g thiophenol and the solvent was removed under vacuum. The resulting viscous oil (2.12 g) was heated with a flame to the reflux point and there was extensive bubbling. After 5 min, the light colored reaction mixture was cooled to room temperature, dissolved in 50 mL CH2Cl2, and extracted with two 25 mL portions of dilute HCl. These were pooled (pale yellow color), made basic with 5% aqueous NaOH and extracted with 3x25 mL CH2Cl2. After removal of the solvent from the pooled extracts, the residue (an amber oil, 1.04 g) was distilled at the KugelRohr. A white oil distilled over at 130-140 °C at 0.1 mm/Hg, and crystallized spontaneously. This distillate weighed 0.77 g, and was recrystallized from boiling hexane after decanting the solution from a small amount of insolubles. There was thus obtained 0.40 g of dimethyltryptamine (DMT) with a mp 67-68 °C. The distillate contained about 3% of 2-Methyl-1,2,3,4-tetrahydro-b-carboline (parent peak mass 186, major peak mass 186) as an impurity which was lost upon recrystallization.

(from tryptamine and ethyl formate) A suspension of 1.0 g tryptamine in 50 mL ethyl formate was held at reflux for 15 h during which time the mixture became homogeneous. The volatiles were removed under vacuum, yielding an oily residue of the formamide. This may be purified by distillation but this unpurified product can serve satisfactorily in the following reaction. This residue was dissolved in 50 mL anhydrous THF and added, dropwise, to a solution of 1.0 M LAH in THF (40 mL, 40 mmole) which had been diluted with another 50 mL THF. After the addition was complete the reaction mixture was heated under reflux for 15 hours. Reflux was continued as a solution of 40 mL 1.0 M freshly distilled ethyl formate in THF was added dropwise over the course of 2 h. Heating was discontinued and the reaction mixture was quenched by the addition of excess solid sodium sulfate decahydrate at room temperature. The reaction mixture was filtered and the filtrate was concentrated under vacuum to yield 1.15 g pure N,N-dimethyltryptamine as an oil which solidified upon storage in the freezer. The material can be recrystallized from hexane to give white crystals with a mp 67 °C.

(from indole) To a well stirred solution of 10 g indole in 150 mL anhydrous Et2O there was added, dropwise over the course of 30 min, a solution of 11 g oxalyl chloride in 150 mL anhydrous Et2O. Stirring was continued for an additional 15 min during which time there was the separation of indol-3-ylglyoxyl chloride as a yellow crystalline solid. This intermediate was removed by filtration and washed with Et2O. It deteriorates at a significant rate at room temperature, and should be used as soon as possible after preparation. The diethylether in this synthesis can be replaced advantageously with t-butylmethylether (TBME) which works well as a solvent in this reaction, but which avoids the potential danger associated with peroxide formation. The above indol-3-ylglyoxyl chloride was added to 20 g anhydrous dimethylamine in 150 mL cold, stirred anhydrous Et2O. When the color had largely been discharged, there was added an excess of 2N HCl, the mixture was cooled, and the resulting solids were removed by filtration. These were recrystallized from EtOAc to give, after air drying, 14.6 g (79%) indol-3-yl N,N-dimethylglyoxylamide with a mp of 159-161 °C.

A solution of 14 g indol-3-yl-N,N-dimethylglyoxylamide in 350 mL anhydrous THF was added, slowly, to 19 g LAH in 350 mL THF which was well stirred and held at reflux temperature under an inert atmosphere. After the addition was complete, reflux was maintained for an additional 16 h, the reaction mixture cooled, and the excess hydride destroyed by the cautious addition of wet dioxane. The formed solids were removed by filtration, washed with hot THF, the filtrate and washings combined, dried over anhydrous MgSO4, and the solvent removed under vacuum. The residue was dissolved in hot petroleum ether. On cooling, crystals of N,N-dimethyltryptamine (DMT) were formed, filtered free of solvent, and air dried, weighing 11.1 g (91%). There have been reports of byproducts from this LAH procedure when performed in Et2O that can compromise the purity of the final product. To obtain the HCl salt of DMT, the residue was dissolved in anhydrous Et2O and saturated with anhydrous hydrogen chloride. The resulting crystals were recrystallized from benzene/methanol to give N,N-dimethyltryptamine hydrochloride with a mp of 165-167 °C. The yield from 14 g of the amide was 13.3 g of the salt.

waste of time imo. i could easily extract an oz of purified white in less than a day.