beta substituted tryptamines

[Plastic Soul]

how come we never see beta substituted tryptamines? Thinkin of something like beta-methyl tryptamine.

          CH3
          |
indole-CH-CH2-NH2

The concept seems to be conspicously absent from tihkal. In fact the only thing a quick google search returned was a reference to an old 60's italian synth of the rather toxic-sounding alpha-phenyl beta-methyl tryptamine.

[EDITED DUE TO SYNTHESIS COMMENTS]

Anyway, i think b-MT would be extremely interesting to compare with a-MT.
Would it be an MAOI? Would the duration be crazy long? Or would it be a
complete contrast with a-MT?


-Maitland

 

[Smyth]

Would it be an MAOI? Would the duration be crazy long? Or would it be a complete contrast with a-MT?

[EDITED DUE TO SYNTHESIS COMMENTS]

In future remember to do your homework before posting random shit off.

 

[Plastic Soul]

Smyth sez:

> Im not god.

haha, i didn't accuse you of being god!

[EDITED DUE TO SYNTHESIS COMMENTS]

*I'm* not a chemistry major! 8)

[EDITED DUE TO SYNTHESIS COMMENTS]

 

[fastandbulbous]

Actually, now that i think of it, I am also kind of curious as why we don't see the analogous sub on the phenethylamine skeleton
either.

Because it does nothing for the potency of phenethylamines. There's a paper by the people at Porton Down (the UK's chemical & biological weapons research facility) that examined altering the side chain of DOM, and what consequences it had on its activity.

From that study, the compound 2,5-dimethoxy-4, alpha, beta-trimethylphenethylamine (beta methyl DOM) only had about 6-7% of the activity of DOM (if does in mg/kg for rats holds true in humans, an effect equivalent to 3mg of DOM would require about 50mg of beta-methyl DOM; beta-methyl 2C-D had activity of about 2-3% that of DOM - that's over 100mg)

I've seen nothing about beta-methyltryptamines, despite looking for any refs for quite a few years now; if the beta-methyl group doesn't interfere with binding to the receptor, it might just turn out to be interesting. I've got a pet theory that while ring substituted 2-phenyl-3-aminobutanes might have a drastically reduced potency, ring substituted 2-phenyl-3-aminobutenes may well be highly active (poss moreso than their amphetamine equivalents).

More detailed explanation here

 

[Smyth]

There are a group of enzymes that break down neurotransmitters such as NE, DA, SER... in-vivo, by oxidizing the amine group [Bear in mind this is not coming from a trained biochemist or biologist]. Apparantly the alpha-methyl group makes the molecule more resistant to enzymatic degradation at this point of attack. Analogy: Warrior (neurotransmitter) uses shield (alphamethyl group) to block opponents sword. Therefore moving the alphamethyl group to the beta-position would be like guarding my legs as the opponent swings shots at my head.

 

[fastandbulbous]

Er... no

Beta-methylphenethylamine is a competetive inhibitor of monoamine oxidase (MAO) with a Ki not too different to that of amphetamine (it's highly potent competetive inhibitors - like harmaline - and non-competetive inhibitors - like phenelzine - that are dangerous in combination with other drugs); both have a similar sort of plasma half life, only beta-methylphenethylamine has no CNS stimulant properties; about the only use for betamethylPEA is as a decongestant or a pressor agent. If comparing alpha/beta methyltryptamines, it's quite possible that they will have similar Ki's as well (AMT's Ki is about a tenth of the concentration of amphetamine - effectivly 10x the competetive inhibition at the same concentration), but that's no guarentee that beta-methyltryptamine will have psychedelic activity, but we can live in hope.


Could the guinea-pigs form an orderly line please!

 

[Smyth]

Monoamine Oxidases are the enzymes responsible and I think the neurotransmitters are converted to their corresponding arylacetic acids as a result of this.

I am running out of steam to fuel these technical arguments since I am outside of an academic institution and dont have access to all the flash literature and computer search engines.

Is there a point to this babble or not?