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Catuabine

DadeMurphy

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"In vitro, T. catigua extract concentration-dependently inhibited the uptake and increased the release of serotonin, and especially of dopamine, from rat brain synaptosomal preparations...The present study provides convincing evidence
for a dopamine-mediated antidepressant-like effect of the active principle(s) present in the hydroalcoholic extract of T. catigua in mice and rats when in vivo and in vitro strategies were employed. Therefore, a standardized T. catigua extract or its purified constituents could be of potential interest for the treatment of depressive disorders."

From "Antidepressant-like effects of Trichilia catigua (Catuaba) extract:
evidence for dopaminergic-mediated mechanisms," Campos et al., Psychopharmacology, 2005.

So, looks like SOMETHING in there is a DARI, and based on structure it would be reasonable to guess it was one of the Catuabines.
 

Reminisant B

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^Interesting.

Do you think it is readily broken down in vivo? Possibly a reason why its success has been limited.
 

vecktor

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Reminisant B said:
^Interesting.

Do you think it is readily broken down in vivo? Possibly a reason why its success has been limited.
just going to type as I think..
this comes from some kind of coca plant
almost certainly the 1-methyl pyrrole 2-carboxylic esters would be cleaved as it is possible for the nitrogen to interact with the carboxylic acid making cleavage much more likely, pyridine 2-carboxylates behave similarily. it is also an amino acid making it a target for specific peptidases. this acid is the aromatic version of n-methyl proline does it have a common name it is also a sort of alanine analog.

just ges to show that the requirements for DAT inhibition are pretty broad. this looks like a benztropine type DAT inhibitor.
 

hussness

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vecktor said:
this comes from some kind of coca plant
how do you know they are related?
almost certainly the 1-methyl pyrrole 2-carboxylic esters would be cleaved as it is possible for the nitrogen to interact with the carboxylic acid making cleavage much more likely, pyridine 2-carboxylates behave similarily. it is also an amino acid making it a target for specific peptidases.
What does the nitrogen have to do with its lability?
just ges to show that the requirements for DAT inhibition are pretty broad. this looks like a benztropine type DAT inhibitor.
Definitely right about that. Any information as to whether or not it binds to the same site on DAT as cocaine?
 

vecktor

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hussness said:
how do you know they are related?

What does the nitrogen have to do with its lability?

Definitely right about that. Any information as to whether or not it binds to the same site on DAT as cocaine?

3 questions 3 answers, might be completely wrong and I might be lying...

I believe that catatuba is still the same genus as coca ie erythoxylum, it certainly has been classified in that genus in the past.

I am not going to go into the details of the mechanism, but essentially the nitrogen atom can increase the lability of the ester by supplying or withdrawing elecrons making the ester bond much more likely to hydrolse chemically. biologically having a nitrogen alpha to a carboxylic acid group makes it much more likely to be recognised and hydrolysed by amidases and esterases as it is close to the normal substrate for these enzymes.

benztropine I believe does not bind the exact same site as cocaine, however ther may be overlap between the sites as benztropines can displace radiolabel phenyltropanes.
 

DadeMurphy

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According to wikipedia:
"It is often claimed that catuaba is derived from the tree Erythroxylum catuaba, but this tree has been only described once, (in 1904), and it is not known today to what tree this name referred. The name E. catuaba is therefore not a recognised species (Kletter et al; 2004)."

Also, correct me if I'm wrong but the nitrogens aren't alpha to the carboxyllic group, and aren't necessary for acid catalyzed hydrolysis anyways.
I'm not sure about enzymatic mechanisms for hydrolyzing these bonds though...
If those bonds do indeed hydrolyze, I would think the resulting compound would be less active at the DAT, since it's basically a tropane + a couple alcohol moieties. But I'm no expert....
 

vecktor

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DadeMurphy said:
According to wikipedia:
"It is often claimed that catuaba is derived from the tree Erythroxylum catuaba, but this tree has been only described once, (in 1904), and it is not known today to what tree this name referred. The name E. catuaba is therefore not a recognised species (Kletter et al; 2004)."

Also, correct me if I'm wrong but the nitrogens aren't alpha to the carboxyllic group, and aren't necessary for acid catalyzed hydrolysis anyways.
I'm not sure about enzymatic mechanisms for hydrolyzing these bonds though...
If those bonds do indeed hydrolyze, I would think the resulting compound would be less active at the DAT, since it's basically a tropane + a couple alcohol moieties. But I'm no expert....

the queastion is that a botanist identiefied it as a erythroxylum so morphologically it must be closely relatede. and it turns out that phytochemically it is also related.

the nitrogen in 1-methyl pyrrole 2-carboxylic acid are most certainly are alpha to the carboxylic acid group.
 
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