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7-substituted-tryptamine & B-dragonfly

Reminisant B

Reminisant B

Greenlighter
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Nov 3, 2005
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Ok so I might be slightly slow off the mark here, possibly this has been mentioned before.

If you look @ bromo-dragonfly & lsd simulating 5-HT as shown in the diagram [and talked about in the nichols paper] would 7-substituted trptamine not be tryptamine equivalents of 2C's?

I.e you could have 7-ethyl-thio-tryptamine being the tryptamine equivalent of 2c-t-2
 

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Is there a reason why shulgin would not have tested any 7-subst-tryptamines?

I'm not 100% on chemistry so would the chemistry involved be complex or impossible>?
 
The chemistry shouldn't be a problem, infact some of it has been done. A quick google turned up a few things, such as:

http://www3.interscience.wiley.com/cgi-bin/abstract/113323216/ABSTRACT?CRETRY=1&SRETRY=0

You'll need journal access to view the article (I hate wiley interbastards I never seem to be able to access half their stuff, even with university logins, I need to get/remember my ATHENS password!)

Interesting structures though, I'd not noticed the similarity before.
 
oops just realised I have drawn 5-ht with an extra methyl group. Still the analogy still holds up. [EDIT should now be correct]

Possibly 5-meo-7-subst-tryptamines to follow the eq 2C.
 
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7-Chloro- and 7-methyl-alpha-methyltryptamine are claimed in some patents as stimulants. 7-Methyl-alpha-ethyltryptamine is similar to alpha-ethyltryptamine (aET) in that it is a serotonin releaser, but it's about 10x as potent and also more efficient (higher maximum serotonin release).
 
^^^

Now that is interesting. I had just assumed that the 7-substituted tryptamines were inactive, but on a quick flick through TIHKAL it looks like Shulgin tested 6-substituted compounds (which were all inactive) but never made any 7-substituted analogues at all.

The only thing I would be wary about is that 5,7-dihydroxytryptamine is a known compound that is a selective serotonergic neurotoxin, used to preferentially destroy serotonergic neurons for research, in the same way that MPP+ or 6-hydroxydopamine are used to destroy dopaminergic neurons in the study of parkinsons disease.

But so long as you avoid hydoxyl groups at the 7-position it looks like it may have potential. I see that 7,N,N-trimethyltryptamine is a known compound, CAS#65882-39-5. Seeing as 2,N,N-TMT, 5,N,N-TMT and alpha,N,N-TMT are all active it would be interesting looking at 7,N,N-TMT as well....
 
...but exactly this made the 2,4,5 subsitution the best on phens!!! (6-ho-dopamin is actually 2,4,5-trihydroxiphenethylamin!)

Now you can see why a 7-Ethylthio with a 5-Methoxi could be the winner-why the hell didn't anyone come up earlier with this??A whole new series starts here,fuck!Even the releasers 10x more potent,some day we will HAVE 10mg MDMA (see the other thread about MDMA susbtitutes!).And the 2-bromobenzyl also fitting in there.And why haded the 5-Tweetios an intact potency,and why the 4-ho needed to suck the amine in its direction with H bridge,look at potencies of MMDA-2 and 3a compared to 3b, 6 versus 2 MADAM, and watch the (stimulant) 2,3-MDA's entry etc

Ah 7-Methoxi-AMT and 6,7-MDO-AMT and many more,here we come!GUTH (Great Unified receptor Theory) for the phens and tryps coming home,we are here,we are complete!

End of manic rant,please rain on my parade now!
 
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That's interesting about 5,7-Dihydroxytryptamine - if a bit worrying about 5-HT's MPTP equivalent.

7-Methyl-alpha-ethyltryptamine sounds an interesting compound.

If only one had the means to investigate these compounds :\ [or ask Shulgin or Nichols]
 

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Possibly 7-subst is the HOT spot for tryptamine much like the 4-subst for PEA's

[? or possibly not]
 

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Great minds think alike...I had drawn this up this morning.

I would bet the analogue 5-MeO-7-MeS analogue of a-MT would be active. Perhaps 5-MeO-7-EtO analogue would be even more potent.

7-sub-tryp.bmp


hugo24 said:
...but exactly this made the 2,4,5 subsitution the best on phens!!! (6-ho-dopamin is actually 2,4,5-trihydroxiphenethylamin!)

Now you can see why a 7-Ethylthio with a 5-Methoxi could be the winner-why the hell didn't anyone come up earlier with this??A whole new series starts here,fuck!Even the releasers 10x more potent,some day we will HAVE 10mg MDMA (see the other thread about MDMA susbtitutes!).And the 2-bromobenzyl also fitting in there.And why haded the 5-Tweetios an intact potency,and why the 4-ho needed to suck the amine in its direction with H bridge,look at potencies of MMDA-2 and 3a compared to, and watch the (stimulant) 2,3-MDA's entry etc

Ah 7-Methoxi-AMT and 6,7-MDO-AMT and many more,here we come!GUTH (Great Unified receptor Theory) for the phens and tryps coming home,we are here,we are complete!

End of manic rant,please rain on my parade now!
Click to expand...
 
What about:

Tryp-2C's - 5-Meo-7-Subst-Tryptamine
Tryp-3C's - 5-Meo-7-Subst-aMethyl-Tryptamine

8)
 
fastandbulbous said:
God I'm so hip it's painful sometimes =D =D =D =D
Click to expand...

This is very true. %)

I can completely understand your excitement now I understand the chemistry & concept. At least we can rest knowing PIHKAL & TIHKAL are far from finished - isoquinolones were sounding a bit dry but wouldn't it be great to have a new book with a whole news series of compounds. [even if it's continued by shulgins apprentices - producing two books is legend enough for one man]

:D

Fast&B do you know how complex the chemistry of such compounds would be? I.e easy as 2c's or complex as dragonflys? [I couldn't access the chem patent link above & prob wouldn't entirely understand it anyway]
 
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certainly of interest purely from a a 'scientific' basis, but sadly does not do all that much for the US contingent with the analogue laws as to legal concerns

i still am surprised i have never seen 2,5-dimethoxy-MDMA assayed and as such curious as well to 6,7-MD-5-MeO-AMT
 
I vaguely remember some stuff from Glennon on 7 substituted tryptamines. there are definately some 7-methoxy tryptamines described by Troxler if I remember right and it is a long time since I read the paper there are human assays for the compounds it was 1959 and things were better then (or so I have heard :) ) and I am certain sandoz patented 7 hydroxy dmt (7 PSILOCIN)...
indeed they did:
http://v3.espacenet.com/origdoc?DB=EPODOC&IDX=CH375713&F=0&QPN=CH375713
 
Reminisant B said:
looks very interesing article 7-subst-T's. Shame I can't understand a word.:\
Click to expand...

it only describes the synthesis, however I am sure the Helvetica chim acta article that corresponds to this patent has assay info. it is in German too :-)
I have had a quick look at my notes
ok people don't hold out too much hope for the grand SAR of everything based on the 7 tryptamine 4 phenethylamine equivalency.

7 Methoxy NN MIPT is reported to have no hallucinogenic effects at 50mg by Repke and Shulgin. J med chem 1985 pp 892 onwards
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=4009612&dopt=Citation
this is the paper where 5meO MIPT and allies are described complete with human tastings, before the analog act
 
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You could always try to ask shulgin through the center for cognative liberty and see what he thinks:\
 
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