phosphor and psychedelics

[Incunabula]

The only drug that I know of that has a phosphor containing functional group is psilocybin.

I was just wondering why we don't see more phosphor containing psychedelics?

 

[bloodshed344]

I've wondered the same thing. Wouldn't a compound like 5-po-dmt have less peripheral side effects than 5-ho-dmt

 

[DJHENRU]

http://en.wikipedia.org/wiki/Ethocybin Thinking of the 5meodmt to mushroom substrate theory producing 4-Hydroxy-5-methoxydimethyltryptamine, but why never this thery reiterated with 4-phosphoryloxy-5-methoxydimethyltryptamine?

"Though this method has never been explored with 5-MeO-DMT, it has been used successfully for changing DET into 4-HO-DET and 4-PO-DET, both of which had never before been found in nature."
http://en.wikipedia.org/wiki/4-Hydroxy-5-methoxydimethyltryptamine

 

[sekio]

organophosphorous compounds are not particularly friendly, toxicologically. most organophosphate "drugs" are things like tabun, soman, VX gas.

Wouldn't a compound like 5-po-dmt have less peripheral side effects than 5-ho-dmt

Not neccesarily. Most of the time they break down rapidly to the HO compounds again.

In humans as well as other mammals, psilocybin is transformed into the active metabolite
psilocin, or 4-hydroxy-N,N-dimethyltryptamine (C12H16N2O.) It is likely that psilocin partially or
wholly produces most of the subjective and physiological effects of psilocybin in humans and
nonhuman animals.

Psilocybin is detectable in plasma 20 to 40 minutes after oral administration (Hasler 1997) reviewed in (Passie et al. 2002). Psilocybin is metabolized in the liver, where it is chiefly transformed into the active metabolite psilocin, detectable in plasma 30 minutes after administration (Hasler 1997; Hasler et al. 1997; Lindenblatt et al. 1998; Passie et al.2002), with psilocin first appearing in plasma 15 to 50 minutes after oral administration of 0.2 mg/kg psilocybin.

http://www.maps.org/research/psilo/psilo_ib.pdf

(Note that psilocin shows up at T+15 but psilocybin at T+20)

 

[Limpet_Chicken]

Fluorophosphate esters/thioesters are a different kettle of fish from a simple phosphate ester.

Another few I can think of are baeocystin, and THC-O-phosphate ester.


And just to be a chem nazi, the currently used nerve agents are not gaseous, in particular, the V-series agents are known to be heavy, oily liquids, and are typically used as persistent, area-denial weapons, rather than tabun and the other G series agents (not sure about the hybrid GV in terms of consistency, I've never made any) which also come into use due to their volatility.

 

[DJHENRU]

I wonder if this is one of the better supported points that plants create hallucinogens as a defense(I don't see the claim substantiated as much with say ayahuasca but whatever) I'm pretty sure for something wanting to eat a large number of mushrooms that sprang up out of hinder could be incapacitated enough to possibly die do to something else in the ecosystem.

 

[Hammilton]

organophosphorous compounds are not particularly friendly, toxicologically. most organophosphate "drugs" are things like tabun, soman, VX gas.

DNA and RNA are also organophosphates. I think as far as actual drugs go there may be a few paralytics which have more in common with tabun than DNA, but I can't think of any off the top of my head.

but we're talking about simple phosphate esters in this thread- simply R-O-P(O)(OH)2, which isn't harmful.