4-PO-Tryptamines?

[Ballz_Trippington]

Sorry if this has been asked before I remember reading a similar thread a while back but could not find it in the search engine.
I was wondering why there only seems to be 4-PO-DMT and not any other Tryptamines like 4-PO-MET or 4-PO-DPT or any other 4-PO Tryptamines? I understand that the 4-PO's are supposed to turn into 4-HO version when it hits stomach acid but since there is some debate as to whether or not the 4-ACO and 4-HO versions are exactly identical when ingested I wondered why the 4-PO versions haven't been explored if the are active besides 4-PO-DMT?

 

[any major dude]

There are a few reasons I imagine. 1stly regarding economics of production, you're going to get fewer doses by weight, which is unattractive to both producers & users. Secondly, if you read the Nichols et al paper on the synthesis of 4-AcO-DMT he mentions problems with yield & the dangers of working with phosphorus.

Pharmacologically speaking, there isn't likely to be much difference between the PO's & HO's and the TiHKAL reports support this notion as well. Though admittedly they did not pick up the differences between the acetates & free phenols as we have. Could be an issue with sample size as his group was quite small.

 

[ZFC]

The psilocin part of Tihkal lumps together "the indolol [4-HO-DMT], the acetate [4-AcO-DMT] or the phosphate [4-PO-DMT = psilocybin]" and it is not quite clear in the individual reports which is the default one. 4-PO-DMT is explicitly referred to as "phosphate ester" and one report is on shrooms. But the five others could be either the free phenol or psilacetin...

 

[atara]

The phosphate esters are remarkably difficult to synthesize with known techniques. It's very rare to see phosphate esters of any sort produced synthetically, even though the transformation is very common in biological systems. It may just be a lack of interest, or, perhaps, phosphorylation is an inherently difficult transformation without enzymes around.

A desirable characteristic of the phosphates is that they're both stable (unlike the indolol) and quite hydrophilic (unlike the acetate). I doubt that'll be enough to motivate using something like dibenzylchlorophosphonate, though.

 

[Ballz_Trippington]

Thanks very much for the info, I have a much better understanding of this now.