Using phalaris with mushrooms (tryptamine cubensis

[myco_chemist5]

what if you grew Phalaris, extracted the DMT, and used it in some of the growth or casing on a batch of fungus. Would the DMT be converted to 4 OH DMT (psilocybin)?

[Rhodium]

Yes, and even tryptamine would be converted to Psiloc(yb)in. UTFSE in this forum for details. Also note that phalaris grass contains a lot of 5-MeO-DMT beside its DMT content.

[moo]

Biosynthesis of Psilocybin, Part II. Incorporation of Labelled Tryptamine Derivatives
Stig Agurell, J. Lars G. Nilsson
Acta Chemica Scandinavica 22, 1210-1218 (1968)

Abstract:
The biosynthesis of psilocybin has been investigated by feeding labelled precursors to Psilocybe Cubensis. The following specifially labelled compounds were synthesized: psilosin-³H, 4-hydroxytryptamine-¹⁴C, N,N-dimethyltryptamine-¹⁴C and -¹⁴C-³H, N-methyltryptamine-¹⁴C-³H and DL-tryptophan-³H. A number of other indoles were labelled by acid catalyzed exchange in tritiated water. The experimental data suggests a sequence: tryptophan --> tryptamine --> N-methyltryptamine --> N,N-dimethyltryptamine --> psilocin --> psilocybin. The fungus can also by an alternative route convert 4-hydroxytryptamine to psilocybin. Large differences in the rate of absorption of different closely related precursors has been observed.


A relevant quote from the article:

However, the results in Table 1 show that 4-hydroxytryptophan which so far has not been encountered in nature, in contrast to tryptophan does not function as a precursor of psilocybin. Tryptamine, which is readily formed from tryptophan by P. Cubensis, serves as a better precursor of psilocybin than tryptophan. If tryptamine is methylated to N-methyltryptamine, this is an even better progenitor of psilocybin with incorporations showing that more than half of the psilocybin was derived from the introduced labelled precursors (Expts. Nos. 38, 42). The corresponding dimethyl derivative N,N-dimethyltryptamine may, however, be considered as a poor precursor as judged from the incorporation percentages.

The culture conditions they used was a submerged culture, described in Acta Pharm. Suecica 3, 67 (1966). To find out why DMT was incorporated so poorly although it is a close relative to psilocin, they measured the amounts of uptake of precursors from medium by P. Cubensis. The uptakes are ordered as follows: psilocin (ca. 80%) > tryptamine (ca.65%) > 4-hydroxytryptamine (ca. 40%) > N-methyltryptamine (ca. 30%) > DL-4-hydroxytryptophan (ca. 25%) > DL-tryptophan (ca. 20%) > N,N-dimethyltryptamine (ca. 5%). The values are measurements after 26 hours, the time after which most of the uptake had already happened. If the DMT doesn't get absorbed, it is no wonder it's not incorporated into psiloc(yb)in. Scanning the whole article is also possible.

Therefore, it might be fruitful to find out plants that contain N-methyltryptamine or/and tryptamine.  

[Rhodium]

Here is the full article quoted from above:

Post 453575

(Rhodium: "Ref 12: Biosynthesis of Psilocybin", Tryptamine Chemistry)

[moo]

Great!