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I Like to Draw Pictures of Random Molecules

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It likes to polymerize... per wiki apparently if you chill the fuck out of it, it'll stabilize enough to work with, so maybe someone out there dedicated enough could figure something out, but the Chinese are so lazy they don't even like synthesizing 6-xapb so I wouldn't get my hopes up. The MDxx derivative clock is kind of starting to run out, I'm curious as to what they'll push out next

Maybe they'll try to unload the rest of their postban APB stock as N-OH-5-MAPB, that wouldn't surprise me a bit



Yeah I was referring to benzphetamine or that atrocity benzedrone, but matter of fact I'll even lump NBOMes in with them. you are right about lysine coming off in a different manner, isn't that done in the bloodstream?

About the stability of isobenzofuran, I suspect keeping in base might lend some stability. I would think that pyrrole polymerises in a similar manner to how isobenzofuran does; pyrrole cannot be used in any reaction requiring a strong acid of pH<-4 or it will polymerise. It seems isobenzofuran is a lot more reactive than benzofuran and pyrrole (maybe because the benzene ring isn't really intact so it doesn't benefit in stability as much as it normally would) but removing any protons which could possibly catalyse (as well as react in) polymerisation might mean it is stable enough for reactions.

When Vynase is administered, lysine is cleaved off in the red blood cells to give dextroamphetamine. I'm not too sure why it happens in rbcs and why it couldn't just happen in the stomach itself; maybe because the stomach enzymes catalyse the breakdown of long chain peptides way faster and have much more selectively for them so that small molecule peptide bonds which require cission occurs elsewhere.
 
Ancient alt.drugs post archived on Erowid, on caffeine analogs

Probably not really viable recreational drugs (where does the methylenedioxy go? :p), but interesting and underlooked chemistry.

There are loads more, and a good bit of research since then on the subject which I'm just sort of delving into now for shits and giggles. I'm snagging a few papers. Could post more if I find interesting stuff and people are interested.

I don't think anyone here minds what kind of molecule it is, even if it doesn't cross the BBB, probably as long as it has a biological action will it remain interesting to me at least.
 
Ancient alt.drugs post archived on Erowid, on caffeine analogs

There are loads more, and a good bit of research since then on the subject which I'm just sort of delving into now for shits and giggles. I'm snagging a few papers. Could post more if I find interesting stuff and people are interested.

Hey, if any other such old gems you know where to dig for over there at erowid exist that don't have sufficient proper academic-chemistry-field coverage, please let me know, I just added that link in due course to the shamefully sparse 'analogs' section of the WP "caffeine" page (whose sole prior contribution, was also given by yours truly)
 
About the stability of isobenzofuran, I suspect keeping in base might lend some stability. I would think that pyrrole polymerises in a similar manner to how isobenzofuran does; pyrrole cannot be used in any reaction requiring a strong acid of pH<-4 or it will polymerise. It seems isobenzofuran is a lot more reactive than benzofuran and pyrrole (maybe because the benzene ring isn't really intact so it doesn't benefit in stability as much as it normally would) but removing any protons which could possibly catalyse (as well as react in) polymerisation might mean it is stable enough for reactions.

would the finished product not still have reactivity issues?

Looking at existing drugs that include isobenzofuran or pthalane -- https://en.wikipedia.org/wiki/Category:Isobenzofurans -- it looks like the big issue lies in the 1 and/or 3 position, on the benzofuran ring, as every example has a substitution sitting on there in some form or another... which in and of itself might be interesting. I wonder how VMAT would tolerate that if at all:

8lSuVEX.png


vloH5Dm.png


oYgkOHw.png


OD6wVao.png
 
If we're taking about hydrogenating isobenzufuran I think it would undergo this reaction pretty easily; I suspect the hydrogenated molecule is a lot lower in energy because now the benzene ring is stabilised. Ether bridges are normally strong. Maybe a substituent on the carbon next to the ether hinders electrophilicity at that carbon. The molecules above might not work at SERT (applies to bottom 2 more so), because a change in angle difference between the aromatic and the ring substituent appears to reduce SERT affinity. Top 2 are flat but then again there seems to be a lot of steric hindrance in the binding cleft. For DAT these molecules would be a lot better.

One hypothesis about how monoamine releasers release monoamines from vesicles is simply by altering the proton gradient simply because they are a base, and as such all of these molecules would act in this respect. Not too sure about how they could interact with VMAT.
 
Well the anhydride will be broken open by water (or saliva, as the case may be) upon contact into the following, and the lactone will be metabolized into the same thing:

1-(3,4-dicarboxyphenyl)-2-aminopropane.png


which is uber electron withdrawing.
 
Lactone would get hydrolysed to this wouldn't it? Maybe further oxidised once in the liver.
2-(1-hydroxymethyl)-5-(2-aminopropyl)benzoic%20acid.png

Still would be too polar probably, and yeah a poor ring as well.
 
Yeah, sucks, ah well

Could do benzothiophene derivatives I suppose but I bet your sweat would smell like utter ass

On a random note I'm still curious as to what MDPV metabolite it was that turned my skin oompa loompa orange after a hearty binge. Maybe I was just tripping out but it happened every time
 
Yeah, sucks, ah well

Could do benzothiophene derivatives I suppose but I bet your sweat would smell like utter ass

On a random note I'm still curious as to what MDPV metabolite it was that turned my skin oompa loompa orange after a hearty binge. Maybe I was just tripping out but it happened every time

Hmm, don't know a lot about sulphur chemistry but the compound should be bioactive most like the benzofuran series. Because sulphur is hypervalent it can be oxidised; when this happens it should lose all SERT affinity; that's if it even gets into the brain in fair amounts which I don't think it will.
 
2CT7 certainly gets into the brain:

2-(2,5-dimethoxy-4-(1-thiabutyl)phenyl)-1-aminoethane.png


It also killed a few people when it was making the rounds as one of the first modern day research chemicals, especially those unlucky enough to have combined it with MDMA.
 
I'm not disputing the fact that thioethers are lipophilic, but S-oxide thioethers are way less so however.
 
Speaking of S,

3-(2-hydroxy-4-(1-thiabutyl)-phenyl)cyclohexanol.png


and

6,6,9-trimethyl-3-(1-thiabutyl)-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-1-ol.png


I sure would like to get stoned.

10a-ethylamino-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-benzo[c]chromene-1-ol.png


I kind of outdid myself with that last one; note the structural skeleton of a classical dissociative afforded by the addition of the 10a-ethylamino substituent to plain ole THC.

Finally,

3-ethylamino-3-(2-hydroxy-4-pentylphenyl)cyclohexanol.png
 
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The first molecule is based on CP-(can't remember the numbers), thought to be the simplest active cannabinoid:

3-(2-hydroxy-4-pentylphenyl)-cyclohexanol.png
 
some 4-thioalkyl phenethylamines are thought to be MAOIs.... i wonder if its just one of the enatiomers that is an MAOI? interesting idea there^.
 
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