Welcome to the Shroomery Message Board! You are experiencing a small sample of what the site has to offer. Please login or register to post messages and view our exclusive members-only content. You'll gain access to additional forums, file attachments, board customizations, encrypted private messages, and much more!
|
 mycelialfruit
Stranger
Registered: 01/04/09
Posts: 21
Last seen: 2 years, 2 months
|
 Interesting shulgin post mushrooms
#9803183 - 02/15/09 02:51 PM (3 years, 3 months ago) |
|
|
Wednesday, December 07, 2005
4-Hydroxy-5-methoxy-N,N-dimethyltryptamine, Psilocybe mushrooms, Psilocin
Dear Dr. Shulgin:
I have been puzzled, why this compound (4-HO-5-methoxy-N,N-dimethyltryptamine) wasnt included in TIHKAL -- for me it looks very appealing. Have you by the way, ever looked into cathinone (beta-keto-amphetamine) analogues of some of the psychedelic amphetamines (DOB, TMA-2, etc.) The MDMA-analogue (Methylone) is active indeed, do you think the 2,4-5-substitution pattern could be applied onto the CATs?
Anon
Dear Anon ,
I totally agree with you.
4-Hydroxy-5-methoxy-N,N-dimethyltryptamine would be a fascinating compound to explore. The reason its not in TIKHAL is that it is virtually unknown. The only report of it in the chemical literature was a paper published by Marc Julias group at the Pasteur Institute in 1965. They reported the synthesis and physical properties of the compound but to my knowledge it has never been explored in any way. The synthesis is quite a frightening thing. It starts with ortho-vanillin and takes approximately 10 steps to get to the 4,5-HO-MeO-DMT. Im not surprised that no one has pursued the compound.
However there is a very interesting study that took place in Leipzig about 15 years ago. Jochen Gartz, a mushroom explorer whom I know quite well, has done some fascinating studies with Psilocybe species by raising them on solid media containing strange tryptamines that are alien to the mushroom. Apparently the enzymes that are responsible for the 4-hydroxy group of psilocin are indifferent to what it is they choose to 4-hydroxylate. He has taken things like DPT or DIPT and put them in the growth media and the fruiting bodies that came out contain 4-hydroxy-DPT or 4-hydroxy-DIPT instead of psilocin. In fact, he has a patent on the process. These active compounds are made by the mushroom so they really are natural and yet they never have been observed in nature. Ill give you even odds that if you put spores of a psilocybe species on cow droppings loaded with 5-MeO-DMT you would come out with mushrooms containing 4,5-HO-MeO-DMT. This way you avoid a 10 step synthesis by growing a psychoactive mushroom that contains no illegal drug.
Your idea of making analogues of the psychoactive amphetamines with the carbonyl that is characteristic of CAT would probably be a disappointment. Cathinone itself is rather unstable because there is a primary amine and a ketone in the same molecule. It will tend to dimerize and become inactive. In the example of METHYLONE (as with methcathinone) the amine is a secondary amine and the compound is quite stable. But all of the psychoactive amphetamines (except for MDMA) are primary amines.
- Dr. Shulgin
posted by CCLE at 9:55 AM
I figured this belonged here...if not excuse me please.
|
RogerRabbit
Bans for Pleasure
Registered: 03/26/03
Posts: 36,974
Loc: USA Mountain Northwest
Last seen: 18 hours, 48 minutes
|
Re: Interesting shulgin post mushrooms [Re: mycelialfruit]
#9803203 - 02/15/09 02:54 PM (3 years, 3 months ago) |
|
|
 This thread has been closed.
Reason:
It's at least the 50th time someone has posted it here. Feel free to search the forum to find the responses for all the previous times it's been posted, but there's no need to rehash it all over again.
RR
| |
|
|
You cannot start new topics / You cannot reply to topics
HTML is disabled / BBCode is enabled
Moderator: Prisoner#1, RogerRabbit, EvilMushroom666
384 topic views. 0 members, 4 guests and 0 web crawlers are browsing this forum.
[ Toggle Favorite | Print Topic ]
| | |
|
|
|
Previous
Index
Next
Threaded
Edit 
Reply 
