5-Methoxytryptamine/Mexamine

[badjessejames]

I accidentally got a gram of this stuff and have no idea what to do with it...
I know it's not psychoactive but is there anything someone with very little chemistry knowledge could do with it to make itfun .

~WhatevA~

[Fuchicoma]

With mexamine you could put out the ol' iodine tinctures and grab some methanol and attack that molecule with some methyl iodide and you could possibly make some 5MeoDMT which is denfinitely an active tryptamine. I suggest you refer to Tihkal under 5Meo compounds and decide your goal. Then try to find a cost effect and accessible route.

[Rhodium]

Using Methyl iodide would probably make more of the quaternary ammonium compound than 5-MeO-DMT.

I suggest you use the procedure in the document below (for synthesis of DMT) and just substitute your mexamine for the tryptamine:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptamine2dmt.html

[cilliersb]

Rhodium...

In the synth proposed by Krz, wha are the implications of using NaBH4 in stead of NaCNBH3. There is quite a difference in price, more like 10 fold for swim.

Any ideas?

[Rhodium]

NaBH4 is untested. It could work with the use of a drying agent, like in the reductive amination of MDP2P with methylamine, but noone knows that yet. A possible problem is the reduction of the pyrrole double bond by formed triacetoxyborohydride in the presence of acetic acid. Maybe by omitting the acetic acid completely, it would work just fine, see

Post 243844

(Rhodium: "Tryptamine reductive alkylation with NaBH(OAc)3", Tryptamine Chemistry).

[cilliersb]

By omitting the GAA, I have no way of controlling the PH.

That would set us back to the original article at DMT world that also produced quaternary salts. The [problem with these is that experimenting, even at nano scale, can be very expensive and time consuming.

What was the verdict on that DMT synth 1 to 4 that was posted by  RDXHMX a while back. Were the crystals that he got DMT or not?

The Iodomethane route seems a lot smoother to perform and yeilds of 50% are acceptable. Any ideas Rhod (I need to either purchase NaCNBH3 or MeI) I only have 45g tryptophan to play with.

Thanks for the feedback Rhod, I can always count on you!!

[Rhodium]

Why do you need to control the pH with acetic acid?

I don't think MeI is a viable alternative.

[cilliersb]

I suppose that Cyano is the route to go, in spite of it's price.

One more thing that was mentioned about a week ago is the Methanolic Formaldahyde Vs. Aq. Formaldehyde. I think that yeilds will suffer dramatically if Aq. is used.

Any ideas about the solubility of Formaldehyde in MeOH? Depolymerizing Paraformaldehy and bubbling this into MeOH at Low Temps will work, but I'm not sure to what extent.

Let me do some reading.

[Rhodium]

5-Cyano-DMT from 5-Cyano-Tryptamine

0.121g (0.545 mmol) 5-Cyanotryptamine HCl was dissolved in 25ml methanol, and with good stirring 0.1ml 30% methanolic sodium methoxide (1 eq) was added, followed by 0.125ml HOAc (2.18 mmol, 4 eq) and  68mg (1.09 mmol, 2eq) NaBH3CN. Next 0.103ml 38% aqueous formaldehyde (1.36 mmol, 2.5 eq) in 10ml methanol was added over 30 minutes. The solution was allowed to stir for 3.5h at room temperature, and 25ml 4M NaOH was added and the methanol evaporated off under vacuum. The residue was extracted with 3x25ml Et2O, the organic extracts washed with 2x20ml brine, dried over MgSO4 and the solvent evaporated to give 5-Cyano-DMT in 75% yield.

Ref:

J. Med. Chem. 44, 3881-3895 (2001)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/reductive.tryptamination-1.pdf)

This method should be general for all tryptamines. The same article also describes the reaction of tryptophol with phenylsulfonylchloride to give the N,O-diphenylsulfonyl derivative in 50% yield, which is then reacted with a dialkylamine and K2CO3 in IPA to give the 1-phenylsulfonyl-N,N-dialkyltryptamine in 65% yield. Is there any way to deprotect that derivative in good yield?