Introduction
Tryptamine is an indolamine derived from the essential amino acid tryptophan. Its chemical structure consists of an indole ring system—a combination of a benzene and pyrrole ring—and a 2-aminoethyl group attached to the second carbon atom (the third aromatic atom, with the first being the nitrogen in the heterocyclic ring). This structural framework is a common characteristic of various aminergic neuromodulators, including serotonin, melatonin, bufotenin, and psychedelic compounds like dimethyltryptamine (DMT), psilocybin, psilocin, and others.
Difficulty rating: 3/10
Equipment and glassware:
- Round bottom flasks 2 L and 250 ml;
- Reflux condenser;
- Drip funnel;
- Separation funnel;
- Funnel;
- Vacuum distillation setup;
- Vacuum pump;
- Buchner flask and funnel;
- Beakers 2L x2; 500 ml x3; 100 ml x3;
- Measuring cylinder 200 ml;
- Magnetic stirrer with heating plate;
- Retort stand and clamp for securing apparatus;
- Laboratory scale (0.1 g-100 g is suitable);
- Freezer;
Reagents:
- Acetophenone 150 ml;
- l-Tryptophan 20g;
- Acetone 300 ml;
- Benzoic acid 12 g;
- Sodium hydroxide (NaOH) aq solution 20%;
L-Tryptophan Decarboxylation
1. To a 250 mL round bottom flask with a magnetic anchor on a securing apparatus with magnetic stirrer and heating plate, acetophenone 150 ml, l-tryptophan 20 g are added.
2. Reflux condenser is attached, the stirrer is switched on, heater is set 240°C. The mixture turns orange.
3. The mixture is refluxed for 4 h.
4. The mixture is turned red after 4 h, cooled down to a room temperature, vacuum distilled from an excess of acetophenone. The red liquid is amine with acetophenone.
5. Acetone 150 ml is added to the red amine solution. The solution is transfered to a larger 2 L round bottom flask.
6. Benzoic acid 12 g in acetone 100 ml is added to form benzoate salt of tryptamine.
7. The flask is moved into a freezer to crystallize out tryptamine benzoate salt.
8. The solid crystallized salt is filtred on a porous Buchner funnel and flask with help of vacuum and washed with acetone on the funnel giving off-white solid 19.1 g.
2. Reflux condenser is attached, the stirrer is switched on, heater is set 240°C. The mixture turns orange.
3. The mixture is refluxed for 4 h.
4. The mixture is turned red after 4 h, cooled down to a room temperature, vacuum distilled from an excess of acetophenone. The red liquid is amine with acetophenone.
5. Acetone 150 ml is added to the red amine solution. The solution is transfered to a larger 2 L round bottom flask.
6. Benzoic acid 12 g in acetone 100 ml is added to form benzoate salt of tryptamine.
7. The flask is moved into a freezer to crystallize out tryptamine benzoate salt.
8. The solid crystallized salt is filtred on a porous Buchner funnel and flask with help of vacuum and washed with acetone on the funnel giving off-white solid 19.1 g.
Tryptamine Free Base Formation
9. To the off-white solid salt of tryptamine, some distilled water is added.
10. An excess of NaOH aq solution is added there.
11. The mixture is heated to near boiling temperature and stirred until an oil forms and no more solid is floating.
12. After that, the mixture is filtered through a cotton to remove the oily layer. The mixture is immediately become cloudy from crystallizing tryptamine.
13. The flask with the mixture is moved into a fridge to cool down. When that’s done, more tryptamine is crystallized out.
14. Next, the mixture is vacuum filtered and than air dried.
The reaction yield is 3 g (19%).
10. An excess of NaOH aq solution is added there.
11. The mixture is heated to near boiling temperature and stirred until an oil forms and no more solid is floating.
12. After that, the mixture is filtered through a cotton to remove the oily layer. The mixture is immediately become cloudy from crystallizing tryptamine.
13. The flask with the mixture is moved into a fridge to cool down. When that’s done, more tryptamine is crystallized out.
14. Next, the mixture is vacuum filtered and than air dried.
The reaction yield is 3 g (19%).
Source
- youtube.com/watch?v=tqbkJHRpiWQ
