Browsing some antique patents, I found something potentially interesting: the synthesis of 4-hydroxy-N,N-dimethyltryptamine-O-sulfates. I have some questions, and I hope somebody can answer them. I will commence by translating the patent.
Patent CH373382
- Verfahren zur Herstellung des bisher unbekannten 4-Hydroxy-N,N-dimethyltryptamin-O-sulfates. Dr Albert Hofmann und Dr Franz Troxler, Bottmingen, sind als Erfinder genammt worden. Sandoz AG, Basel. Zusatzpatent zum Hauptpatent
Patent CH371116
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The synthesis of 4-hydroxy-N,N-dimethyltryptamine-O-sulfates, a former unknown compound.
We found that 4-hydroxy-N,N-dimethyltryptamine-O-sulfate (psilocine-O-sulfate, POSO3) can be obtained if psilocine (P) is reacted as an alkaline salt in an inert organic solvent with chlorosulfonic acid.
Procedure: A solution of 58 mg Na in 30 mL absolute EtOH is charged with 510 mg P (N2 atmosphere). After 15 minutes, the solvent is evaporated and the residue is stored in vacuo for another hour (very low vacuum necessary) at 70°C. Subsequently, 20 mL 1,2-dimethoxyethane and 305 mg chlorosulfonic acid are added. The reaction mixture is damped in after one hour and the residue chromatographed with a 50x mixture of cellulose powder and water-saturated n-BuOH. When the fractions are damped in, POSO3 will crystallize. Crystallization from MeOH yields needles, mp 251-252.
Keller spot test: "koenigsblau"
Van Urk spot test: "dunkelblauviolett"
So far the short patent. Now, my question(s) and why it might be interesting. Psilocine and its phosphate ester psylocibine are both scheduled substances in most countries. In a handful of regions, magic mushrooms containing the substances are tolerated.
It is known that psylocibine is metabolized to psilocine in the human body, which gives rise to the belief that psilocine is the actual active component of magic mushrooms. However, does the same happen with POSO3? Will the sulfate metabolize in the human body to psilocine as well? If yes, then we might have a nice legal alternative. You see, many countries list psilocine, psylocibine and various species of magic mushrooms as scheduled substances, but not POSO3. You could synthesize POSO3 and sell it on the hallucinogenic market as such, without doing anything illegal (depends on the laws of your country. The US Analogue Act...). And the effects will be similar. So, anyone who can answer the question?