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The Large and Nifty Not-quite-advanced Drug Chemistry, Pharmacology and More Thread

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^^^
its probably fine, titrate from a low dose and be aware of potential adverse reaction i assume they are just being super-cautious as there might be a chance of hypotension or something.


QUESTION: i have a vague memory of a paper (perhaps referenced by shulgin?) regarding an experiment that demonstrated claviceps fungus or something of that nature could biosynthesize LSD under certain (experimentally manipulated) conditions - does anyone know what im talking about?
 
hamhurricane said:
QUESTION: i have a vague memory of a paper (perhaps referenced by shulgin?) regarding an experiment that demonstrated claviceps fungus or something of that nature could biosynthesize LSD under certain (experimentally manipulated) conditions - does anyone know what im talking about?
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yes I know the paper you are thinking of, I think it is published somewhere unexpected like Nature, the researcher was English and I think the reference to it is in the Merck index, not got it to hand. They basically screwed around with the broth in submerged claviceps culture to get a mixture that included LSD I am pretty sure they were using C paspali.
 
Dresden said:
Hi. I have a quick and not so advanced chemistry ? that has nothing to do with drug synthesis per se for once.

benzene --> phenol

is a facile enough transformation i guess as it involves the thermodynamically favorable process, ie exothermic oxidative combustion of a simple HC by O (ie, 'burning'), but what about its reverse rxn?

benzene <-- phenol

I have always been under the impression that this pathway is all but impossible but <vecktor> has recently mentioned something involving OTT leaving groups and thallium that has my curiousity piqued. Is this reverse rxn feasible chemically and if so how specifically? thx.
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an example of phenol to benzene conversion, there are loads of variations and this chemistry is very useful in natural products chemistry.

http://linkinghub.elsevier.com/retrieve/pii/S0040403900852624

First the phenol is converted to its triflate ester prior to the reaction the triflate group is a good leaving group more importantly it cleaves off taking the phenol oxygen with it and is replaced by palladium, the palladium complex is then reduced to liberate the benzene in this case and is then free to react with another aryl triflate.

Ironically phenol from benzene is actually difficult!!!

thallium is used to selectively metallate the 4 position of indole as in the following example

http://www.erowid.org/archive/rhodium/chemistry/lysergic.hendrickson.html
 
Thanks, vecktor, palladium is just such a damned useful element.

Phenol can be had from benzene by formylation followed by treatment with hydrogen peroxide.
 
thanks vecktor, i found something quite similar in nature detailing the production of lysergic acid methylcarbinolamide and Lysergic acid hydroxyethylamide, but nothing referencing LSD just close relatives. if anyone is able to find this paper i would be very thankful for the ref.
 
hamhurricane said:
thanks vecktor, i found something quite similar in nature detailing the production of lysergic acid methylcarbinolamide and Lysergic acid hydroxyethylamide, but nothing referencing LSD just close relatives. if anyone is able to find this paper i would be very thankful for the ref.
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I remembered right, surprised really given the onset of senility here. entry 5665 in the Merck index 12th edition Lysergide, Microbial formation by Claviceps paspali over the hydroxyethylamide: Arcamone et al Proc. Roy. Soc (london) 155B 26 (1961)
The royal society has screwed around with its journals and I couldn't find the paper online, I once read a paper copy it was not very efficient if I remember right.
 
vecktor said:
I remembered right, surprised really given the onset of senility here. entry 5665 in the Merck index 12th edition Lysergide, Microbial formation by Claviceps paspali over the hydroxyethylamide: Arcamone et al Proc. Roy. Soc (london) 155B 26 (1961)
The royal society has screwed around with its journals and I couldn't find the paper online, I once read a paper copy it was not very efficient if I remember right.
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DOI: 10.1098/rspb.1961.0056

No access to me; therefore just the DOI and not the full paper.

- Murphy
 
Sorry if this has already been asked but what is the safety profile of the SSRE "Tianeptine" or brand-name of "Coaxil?" The Wikipedia entry has an entry about someone taking many hundreds of tablets a day for a 6-month period and it resulted in nothing more than a need to quickly stop administration of the drug as I can't even imagine what he/she was aiming for.

I am going to be in the Russian Federation this summer and am trying to find a semi-comprehensive list of what exactly is more legal in the C.I.S. states than perhaps in the USA or Europe even. I am looking forward to both large amounts of Carphedon/Phenyl-Piracetam which is a nootropic-style stimulant, and the aforementioned Tianeptine/Coaxil. Any comments on these two choices or very-obvious other drugs I should be dipping my nose towards?

Edit: Want to know a bitch about travelling to Russia? I can't bring my methadone into the country without a special note of exception which I refuse to bribe an official to get; so here's to a taper of awesome speed~!
 
ebola? said:
Obvious, but dude, if you 'need' mephedrone, you should take a break from mephedrone.
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Methadone is not equal to mephedrone. I've done it before too, don't worry; they are very much too-similar. I vote a name change and/or we will start using 4-MCC as its proper chemical classification!
 
I feel kind of foolish for asking this being an ED moderator and all, but I have a few questions about MDMA that have been bothering me for a while. Some of them are more assumptions than questions, so I'll just state those and you can disagree with them if they're wrong.

I'm also going to ignore MDMA's effect on DA and NE for the time being, because I assume that those systems are less likely to be significantly disturbed by occasional MDMA use.

First off, what exactly does it mean for SERT to be "reversed" by MDMA? Does 5-HT just start spilling out of the transporter or is some other action required (for instance, 5-HT binding with the transporter on the outside for reuptake)? Does this "5-HT dump" only in the brain or in the PNS as well, and if it does occur outside the brain does it have any known side-effects? I imagine that it would cause some gastronomic and vascular issues, since 5-HT also mediates those systems.

Also, is the amount of 5-HT released proportional to the dose, or is there a critical dose over which a "serotonin-releasing cascade" begins, releasing some percentage of one's total 5-HT reserves regardless of additional dosage? Is it even correct to think of MDMA as releasing a percent of one's 5-HT, or is it better to think of it as tipping the scale toward greater release over production? Since 5-HT is constantly being produced, it seems unlikely that one could "run out of serotonin". Is it even possible to function with no serotonin left? Does the brain somehow increase serotonin production after depletion?

I think I'll stop there, but I have a few more questions which I'll pose depending on the response to these ones. I greatly appreciate any answers at all. :) Thanks!
 
Well I'm not an expert but AFAIK it goes like this: SERT moves serotonin from the synaptic cleft into synaptic vesicles, and MDMA binds on the SERT protein and changes it's conformation so that this action reverses, and SERT will start moving serotonin from the vesicles to the synaptic cleft. As a side-effect some MDMA molecules will find their way in the vesicles, which causes neurotoxicity...

I might be completely wrong here, that's just the impression I got.
 
That makes sense, thanks. :)

I suppose I'm just not clear on the "reversal" bit -- what does that mean in a functional sense? As far as I understand, once the reuptake transporter into a vesicle it floats around freely inside the cell until an action potential causes the vesicle to merge with the cell wall, releasing its contents outside the cell. Does the transporter in its reversed state actually attract serotonin-filled vesicles and release their contents outside the cell? This seems strange to me, but would be a "reversal" of its usual action.

On the topic of neurotoxicity, is it known that it's a direct metabolite of MDMA that causes neurotoxicity? Has the dopamine theory been discounted by now? We're a little behind the times on interpreting the research on ED, unfortunately.

Perhaps this warrants its own thread on second thought...I'm not too clear on the ADD protocol. :\
 
Yes, it is known that a direct metabolite of mdma causes the purported neurotoxicity. Mdma itself directly added to the brain does not cause neurotoxicity at recreational doses. The metabolite is 3,4-dihydroxy-methamphetamine.
 
AFAIK (not a pro in this area), there's some sort of synergy of mechanisms that effect MDxA's neurotoxicity. Basically, conditions that combine to promote the formation of free-radicals and those free-radicals' entry into neural cell bodies are to blame. So these include increased body-temperature (hence the lack of neurotoxicity of MDMA administered to the brain directly (5ht and the catecholamines increase body temperature...as does dancing to up-tempo music :/)), toxic metabolites of MDxA itself, and then entry of toxic metabolites of dopamine into cell bodies via SERT (these metabolites formed either within or without the cell). The latter explains why selective 5ht releasers don't exhibit neurotoxicity.

But I'm less of an expert than the above people claiming a lack of expertise. ;)

ebola
 
What do we know about the neurological effects of 2-aminoindane (unsubstituted)? To the extent that we remain ignorant, what do y'all speculate?
 
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