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⫸STICKY⫷ I Like to Draw Pictures of Random Molecules

sekio

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IUPAC for that is 8-methyl-7-phenyloctahydroindolizine. (the fused piperidine-pyrrolidine is known as indolizidine). Stereochemistry at 7, 8, 8a.

(7S,8S,8aR)-8-methyl-7-phenyloctahydroindolizine - just picked a random set of chirality to illustrate the 3 chiral centers.

A related compound: (+)-ipalbidine. No idea on its pharmacology, but it looks familar, no?


Also, aziridines are not the most stable things.
 

Gaffy

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Thank you Sekio! 😁🤩 I will update my signature.
Oh.. that's probably why I never came across any aziridine PEA..

Yes, it should be a metabolic compound of it?
 

Gaffy

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IUPAC for that is 8-methyl-7-phenyloctahydroindolizine. (the fused piperidine-pyrrolidine is known as indolizidine). Stereochemistry at 7, 8, 8a.

(7S,8S,8aR)-8-methyl-7-phenyloctahydroindolizine - just picked a random set of chirality to illustrate the 3 chiral centers.

A related compound: (+)-ipalbidine. No idea on its pharmacology, but it looks familar, no?


Also, aziridines are not the most stable things.
It seems ipalbidine comes from a plant! :) Could the ipalbidine be turned into 8-methyl-7-phenyloctahydroindolizine ? The phenyl version of ipalbidine could be good as well but just doesn't seem as good as the piperidine version.
Searching for it renders only one result from a book citing plant alkaloids. No other results.
Did you find it via STP? If so there must be a paper about it, maybe 8-methyl-7-phenyloctahydroindolizine has already been synthed and biotested as a derivative thereof.
 

sekio

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Could the ipalbidine be turned into 8-methyl-7-phenyloctahydroindolizine ?
Not easily: the phenyl group is on the "wrong" side of the indolizidine. It would yield 7-methyl-8-phenyloctahydroindolizine if you could hydrogenate it and somehow also pull the hydroxy off.

Did you find it via STP?
Nope, googling for indolizine alkaloids. I only found a structure, no idea what the activity might be.
 

Gaffy

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STP is taboo but I can tell you that my little finger told me it has mainly D2, D4, SER and overall DOPA action predicted by my little finger's best friend.

Efit: You're right, :'D, I didn't even pay attention to all the postioning that was going on.. My bad..
 
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sekio

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Your 8-me-7-ph-indolizine (in what I view as an example of the "monkeys on typewriters" experiment) actually is one of the better performing compounds when put into STP. I don't know whether to congratulate you or accuse you of plagarism... ;) The "magic 8 ball" suggests it should be some sort of triple monoamine reuptake inhibitor, affinity for VMAT as well, sigma receptor affinity, and possibly D2 receptor binding as well. To me, that sounds like a potential recreational drug candidate.

Now, don't go crowd funding a synthesis quite yet though :) If anything, try to come up with a synthetic route, from commercially availiable reagents if possible. Treat it like a retrosynthesis exam.


CHEMBL416959 and CHEMBL1743824, presumed serotonin transport inhibitors.

The similarity to McN5652 is well noted. The structure reminds me a bit of sertraline too.

(I will make a serious pharmacologist out of you yet!)
 

Gaffy

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On another topic; My bike just got assaulted by two hash-junkies blasting rap, who entered my residency.. Backbrakes stolen along with the suspension's screws, I think they where going for the whole suspension (worth around 150 bucka on its own, Fox suspensions, best there is.)
Lucky I live in a crowded residency where people are on the watch out, the thievers must've gotten spotted as they didn't get the whole set. Still, the brakes they stole are worth 50-100 bucks, they're hydrolic. I'll go to the cops to deposit a complaint tomorrow, as a good citizen, I'll have to check if my bike is insured. ;) There are probably cameras in my residency, at least there should be given they just spent around 800k on renovations. I'll make shure to ask the police to check for other residency cameras, maybe it's not their first go at it. I somehow suspect either my father (lol?) who once told me he was a thief, and warned me just two days ago to stash my bike, or my residency's guard, who has been (weirdky not these last few days) quite impolite and once even agressive with me (and arabian, just like the thiefs, which I sae from my balcony as they left). Anyway..
These might just be what are just speculations.

Next step is getting the Chinese to start pushing GAFFY and the likes, maybe 2025? When iHexen and other caths will have gone out!
Can't wait to try it! :D

At least, a worthwhile design; and guess how.. carrying my name ! 👽
Heh!
 

Gaffy

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Ethyl 2-(Piperidino)-1-3'-hydroxyphenylcyclohex-3-ene-1-carboxylate

I also like this one. Can't post STP results but it seems lile a winner.

 
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clubcard

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I THINK you need a ketone next to that N. Tertiary amines only seem to be active due to the interaction of ⭕ & N:

Who knows if that Tocris ligand is any fun at all. Back in the day I had to tell someone to dump 10kg of 4-MTA that they accepted to clear a debt. I told him how dangerous it was and would he want his kids taking it... it was dumped.

Now, I DID do a deal of work into aminorex series and I am prepared to bet that the p-Me analogue of the McN compound will have potent SRI activity and thus won'tbe fun alone. a 2:1 mixture of p-Me & m-Me is likely good with or without 4-Me.

It's important to see how this class evolved and how a rigid analogue was developed. AFAIK it has yet to be tested in man. As long as Me oxidation is the overriding metabolic path, I would be dubious. For those looking for a high potency I would suggest that the (thiomorpholine analogue of desoxypipradrol is worth looking act. If I wanted it to be complicated, I would demand a p- or m- Me on them at least to begin with but I think the S will result in redistribution.... but I don't know, I am just giving an opinion. We didn't go down this path because (drum roll) it was too complex for the French.... and how many times have I had to say that!
 

Gaffy

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I THINK you need a ketone next to that N. Tertiary amines only seem to be active due to the interaction of ⭕ & N:

Who knows if that Tocris ligand is any fun at all. Back in the day I had to tell someone to dump 10kg of 4-MTA that they accepted to clear a debt. I told him how dangerous it was and would he want his kids taking it... it was dumped.

Now, I DID do a deal of work into aminorex series and I am prepared to bet that the p-Me analogue of the McN compound will have potent SRI activity and thus won'tbe fun alone. a 2:1 mixture of p-Me & m-Me is likely good with or without 4-Me.

It's important to see how this class evolved and how a rigid analogue was developed. AFAIK it has yet to be tested in man. As long as Me oxidation is the overriding metabolic path, I would be dubious. For those looking for a high potency I would suggest that the (thiomorpholine analogue of desoxypipradrol is worth looking act. If I wanted it to be complicated, I would demand a p- or m- Me on them at least to begin with but I think the S will result in redistribution.... but I don't know, I am just giving an opinion. We didn't go down this path because (drum roll) it was too complex for the French.... and how many times have I had to say that!
You do that, (ketone) , I'll keep it as it is :)
 
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