jim (Hive Bee)
08-26-01 19:34
No 207630
      Alkylating tryptamines...  Bookmark   

I have heard a lot of discussion that DRONE's suggestion of using PTC conditions and a slight excess of MeX won't work for tryptamines.

What is the consensus?

Does it, or doesn't it?
(Hive Bee)
08-26-01 20:22
No 207649
      Re: Alkylating tryptamines...  Bookmark   

Surely a few bees have tried and failed.  Only Drone can say for sure, and off to where he has gotten of late I do not know.
08-27-01 07:06
No 207711
      Re: Alkylating tryptamines...  Bookmark   


Why the method is bunk even W/ PTC's is because you yeild the quaternary ammonium salt of said product. Once that happens "a done bun can't be undone". Every attempt made by any of my sources (from Shulgin to Calamus and the rest of the B's)to try to decompose this into the desired active "goodies" have either failed or resulted in piss poor yeilds not even worth bothering to mention. From calculated bond enthalpy you can tell that the process is irreversable do to loss of Gibbs free energy. Entropy is such a bitch!

Yours in science

(Hive Bee)
08-29-01 00:20
No 208241
      Re: Alkylating tryptamines...  Bookmark   

Maybee you should check p 412 of TIHKAL.  Shulgin uses LiEt3BH
(Hive Addict)
08-29-01 15:18
No 208411
      Re: Alkylating tryptamines...  Bookmark   

They used to talk of ethanolamine being able to transform the quanternary amine salt to dimethyl amine however I have yet to hear anyone verify it or post a good reference.

Anyone know about this ethanolamine demethylation?
Tried it? Successfully or Unsuccessful?
Have a reference for it?

Somebody has to have attempted this

Do Your Part To Win The War
(Chief Bee)
08-29-01 17:01
No 208450
      Re: Alkylating tryptamines...  Bookmark   

JMC 13, 254 (1970) talks about using 15min reflux with ethanolamine to demethylate a quat.
(Hive Bee)
08-29-01 17:50
No 208462
      Re: Alkylating tryptamines...  Bookmark   

JMC?  I'm sorry my brain must not be working, What does JMC stand for?  Journal of Medicinal Chemistry?
(Chief Bee)
08-30-01 03:25
No 208595
      Re: Alkylating tryptamines...  Bookmark   

You are correct.