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I Like to Draw Pictures of Random Molecules

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sekio said:
when there are a pair of chiral centers next to each other, there is a cis/trans or erythro/threo/meso relationship :)

you are correct about the swirly lines meaning the bonds can either stick out front or behind the paper. however only sp3 carbon bonds that are unconstrained can rotate - like the bond between the two carbons in ethane. if it's constrained in a ring then bond rotation would invert or pucker the ring and there can be a singificant energy barrier to that.
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Thanks, I get it now :)
 
Ajenks420 said:
How do you do this?? Always wanted to know if you can make like a mdma-dxm-psilocybin(or psilocin)? Anything like that haha
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Fortunately, not really.. DXM and MDMA are very dangerous to mix so having them combined in one drug if that were possible would be a recipe for disaster.

Hybrids of existing drugs, what you seem to be talking about, well you can draw them, you can even make them. But in most cases it won't act the way you want it to. The compromise you make by modifying a molecule so heavily is that it usually doesn't work anymore like the original drug, so combining 2 or 3 drug molecule structures you end up with a molecule that is likely to fail to act as either of them let alone as a combination of all of them.

However, sometimes there is a sort of overlap where different kinds of SAR seem to come together. (SAR is the relationship between structure of a drug and what it does)

For example, bk-2C-B involves making a psychedelic into a cathinone which is usually something done with stimulants. The overlap is that both various psychedelics as well as a lot of stimulants are phenethylamines and that 2C-B is forgiving of this modification to some extent.

@chirality / cis-trans isomerism: thanks for clarifying guys!
 
Raihiar said:
sorry, not really advanced but.. i don't immediately see the cis/trans isomerism - is it on the "piperidine" subunit where the two chiral centers are next to each other? i guess i can see it now, i was just conditioned to only see it on C=C bonds %)
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sorry I missed that thread re cis/trans, R S isomerism of piperidine fanta related. got kick out the shelter and trying to stay warm but anyhow, you got pretty concise answers from the guys for your question. Here is a picture to summarize:
marvinjs-output%202_zps7z9dslyn.png


The 2 groups COCH3 and NMePh can be cis (Z zusammen, same side) of the piperidine ring or trans (entgegen, opposite side) of the lateral plane of the ring. This is the commonly used nomenclature to describe their relationship just like with the cis-trans stereoisomerism of olefins. (@solipsis: actually, in general the E/Z or cis/trans nomenclature refers to the 2 "biggest" substituents (according to Cahn Ingold Prelog rules. But it is usually pretty loosely as it is obvious in general what one is talking about).

Since the C3 and C4 carbon are chiral you'll have, as already noted: RR, RS, SR and SS. Multiply that by 2 of course for each structure since the carbon alfa to the piperidine is also chiral. Therefore you ended up with 8 possible configurations.: RRR, RRS...etc

In term of OP activity, the reason why this is relevant is that in the case of fanta substitued at C3 by a methyl and a 2-fluoro on the Phenyl ring, only one isomer the cis 3R,4S,βS is active at about 18000X more potent than morphine; the others are pretty much "inactive". But this is not really an issue here because it is so potent it won't make a difference I mean the mixture of the 8 stereoisomers or a pure enantiomer! 1/8 of 18000 you still get 2250x more potent than morphine or about 20x more than fanta! Deadly shit!! so caution
 
Well thanks for the ton of answers!
I remembered that the same applies for different sugars (they are a mess in that regard)... I just didn't spot it right away, but i'll keep my eyes open next time ;)
 
Yeah only you'd link DXM onto the 4-position of psilocin rather than the 5 - and you could consider making it just one nitrogen where you link DXM and MDMA rather than a hydrazine.

Actually that does make me wonder about this compound somehow:

3-%5B2-(Dimethylamino)ethyl%5D-4-methoxyindole.png


3-[2-(Dimethylamino)ethyl]-4-methoxyindole

Do you think it could tell us something about the probability of 4-AcO-DMT being active itself or just a pro-drug?

Or instead a better ester bioisosteric group, without having it turn into psilocin:

3-%5B2-(Dimethylamino)ethyl%5D-indol-4-oxy(trifluoromethyl)ethane.png
3-%5B2-(Dimethylamino)ethyl%5D-indol-4-oxycyanoethane.png


However I can't get opsin to properly remove the ambiguity about where fluoros are if I were to use isopropane in the nomenclature instead of cheating by using trifluoromethylethane. 2' prime locant designation doesn't work. Any help with that?
 
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sekio said:
benzoylphenidate more like
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Agreed, but my rationale is the molecular "length" which is closer to isopropyl,
The ipso- position is the same place of Oxygen in mph. Where the rest aromatic bulky occupies approximately same space of isoporpyl group (apart from the flatness differences)

"Benzoyl" phenidate is one oxygen longer
 
Solipsis said:
Yeah only you'd link DXM onto the 4-position of psilocin rather than the 5 - and you could consider making it just one nitrogen where you link DXM and MDMA rather than a hydrazine.
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Thanks, yes I know. It was early and I hadn't had my coffee yet :)
 
^^ yes It looks much closer to iPr-phenidate in terms of steric factors. more like a bioisosteric replacement of the COOiPr with a COPh. Not a COO2Ph! But actually I was thinking more along the lines of replacing pipradol with one with a keto stuck in between the Phenyl ring and the benzylic tertiary carbon. That way may reduce the ridiculously long half-life of pipradol (up to 3 days!!) while retaining its activity. + adding a keto (or similar COOMe like in MPH) to stims seems to shift their activity from AMPH-like to cocaine-like as in MDPV, MPH....etc .. but who knows?

200px-Desoxypipradrol.svg.png

https://en.wikipedia.org/wiki/Desoxypipradrol
 
1-%5B1-(1-Benzothiophen-2-yl)cyclohexyl%5Daminoethane.png


beneticyclidine

(2-phenyl-1-(2-thienyl)ethyl)-N-isopropylamine.png


isophetenidine

2-(2-chlorophenyl)-2-methylamino-1-ethylidenecyclohexane.png


ketenamine

1-(1-phenyl-3-methylpent-3-enyl)piperidine.png


phenpentidine

1-methyl-1-phenyl-1%2C2%2C3%2C4-tetrahydroisoquinoline.png


mephentiquine

1%2C1-diphenyl-1-(ethylamino)ethane.png


diphendetamine

1-benzyl-1%2C2%2C3%2C4-tetrahydroisoquinoline.png


benzyltiquine (intriguing..)
 
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Who knows? but here is an old BL thread I dug up http://www.bluelight.org/vb/archive/index.php/t-361085.html.. the following dimethylamino congerner is supposedly an opioid equipotent to morphine NOT a dissociative!!.. very strange!

@fastandbulbous:
cyclohexanone.jpg


This much simpler molecule is supposed to be equipotent with morphine. Given that the synthesis is so simple, I can see this stuff turning up somewhere or other.


Now that is so close to being an NMDA antagonist that I'd reckon any analgesic effect in rats rtc would be due to it's dissociative effect. That structure is effectively covered in a paper on PCP SAR studies I read qute a while ago (mentions alterations in potency by a) changing the amine group from a 1-piperidyl & 2) moving the keto group of ketamine around the alicyclic ring .. http://www.bluelight.org/vb/archive/index.php/t-361085.html
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