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🌟🌟 Social 🌟🌟 Rectify's molecular poetry thread

1-dimethylamino-1-(3-methoxyphenyl)--4-(4-hydroxyindole-3-yl)cyclohexane.png


PATAGONIA
1-dimethylamino-1-(3-methoxyphenyl)--4-(4-hydroxyindole-3-yl)cyclohexane
 
New Order, "Here To Stay."

Who is this man that follows me?
This blue-eyed boy who wants to be
This worthy cause of humankind
This pawn set up by time

[Chorus]
Like a bright light on the horizon
Shining so bright, he'll get you flying
He'll drive you away, he'll drive you insane
But then he'll remove all of your pain

Like a bright light on the horizon
Shining so bright, he'll get you flying
He'll get you flying, he'll get you flying
He'll get you flying, flying, flying

[Verse 2]
This open book yet to be read
This second look, this leap ahead
The hope I held inside
With you, was kept alive

[Chorus]
Like a bright light on the horizon
Shining so bright, he'll get you flying
He'll drive you away, he'll drive you insane
But then he'll remove all of your pain

Like a bright light on the horizon
Shining so bright, he'll get you flying
He'll get you flying, he'll get you flying
He'll get you flying, flying, flying

[Bridge]
We're here to stay
We're here to stay
We're here to stay
We're here to stay
We're here to stay
We're here to stay
We're here to stay
We're here to stay
 
Cebranopadol is a rigid BDPC derivative. The latter a metabolite. I don't know but would guess that the latter has lower MOR affinity given that N-desmethyl BDPC demonstrated that fact.
 
Cebranopadol is GRT-6005, Lexanopadol is GRT-6006 which makes sense as Grünenthal would likely have begun with the tertiary amine and then tested a potential metabolite.

BUT it looks like the patent is about to run out on both. I already mentioned that on average a company is only left with 7 years of patent protection as development takes 13 years. But with three (?) years left? Unless they can find some AMAZING advantage that will allow them to charge a fortune....

You might be witness to a hard lesson in drug development - unless someone can find a new way to obtain patent protection... all of that research will come to naught. The stuff might be amazing, but nobody produces for fun. Protit is king. Have you noted all the various code-names? It seems like the right have been sold on more than once... each time it had a POTENTIAL worth but as time goes on, that worth tends to ZERO.

I see no reference to testing since 2014.

Olinceridine was patented in 2012 and is IN USE. They HAVE a further 7 years of patent protection.

So no - this drug will never be used. NOP ligands clearly have their own issues. Of course, without www.alltrials.net, we don't know what those issues are. But many have been produced going all the way back to the 1960s. Janssem didn't know they had a NOP ligand but they certainly researched a lot more than they published and then gave up.
 
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Rectify said:
1-(3,4-methylenedioxy-5-methoxyphenyl)-2-aminocyclopentane.png


TEXACO
1-(3,4-methylenedioxy-5-methoxyphenyl)-2-aminocyclopentane
Click to expand...
This one, "BRUCE" and "PETER" remind me of the aminorex series. (Side note: All My Aminorexes Live In Reno, Texas is a live album I haven't recorded yet, but I digress.)

Point is: I'm willing to bet these are all likely active. What do you think? Hell there's even a very much active 3,4-methylenedioxyaminorex. Of course I'm talking about 2-amino-5-aryloxazolines.
 
Those are all cypenamine derivatives.

For a start their are 4 enantiomers and only one of them is active.

ibb.co

idiot hosted at ImgBB

Image idiot hosted in ImgBB
ibb.co ibb.co

cypenamine is sold as the trans-pair but that only has 25% the potency of amphetamine. Not DEXamphetamine, plain raecemic amphetamine. So one concludes that the N: isn't in the optimal spatial position relative to the aromatic.

Shulgin made TCB-2 and 2CB-Ind which only have one chiral centre. But 2CB-2 is significantly more potent so would seem a more fertile area to pursue. I note the NBOMe derivative has been made but that whole class concerns me. Too many deaths without anyone clearly stating what makes them dangerous.

FYI the O in the NBOMes overlays the O= of the amide function of LSD. The aromatic ring just fills the lopophilic pocket, as best as I can tell.

I would look at the -3-phenyl-norbornan-2-amine class. although technically it has three chiral centres thus 8 possible enantiomers, the trans isomer is more energetically favoured so you only end up with two. I doubt you can simply plonk the same ring-substituents as are seen on the simple PEAs but both fencamfamine (the prototype) and camfentamine (the RC homologue) are noted for having opioid activity. I presume because they overlay nortilidine rather well. So figuring out a way to add an ester moiety to the benzylic carbon would, I expect, produce something in the M range.

So if you figure out a way to do that, answers on a postcard to the usual address...
 
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cypenamine is not 4 enantiomers. it exists as a diastereomeric pair of enantiomers (or as a racemic pair of diastereomers).

TCB-2 was not discovered by Shulgin either, it was only discovered in 2006 by Thomas McLean working in the lab of David Nichols at Purdue University.

There's an agent based on cis-cypenamine called MDL-12330A.

Myself and 4DQSAR already had an interesting discussion on Cypenamine type analgesics.

Derek P. Reynolds, US4291059 (1981 to Glaxo Group Ltd).

The benzhydryl analog of cypenamine is also worth of a look at: 2,2-Diphenylcyclopentan-1-amine.

https://orgsyn.org/demo.aspx?prep=CV9P0362
https://doi.org/10.1002/recl.19620810303

Now the compound only contains one stereocenter so it is only 2 enantiomers to consider.

It's an isomer of Pub 105. This in turn is related to 3,3-Diphenylcyclobutanamine.
.
 
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I stand corrected - 4 stereoisomers. But I feel the number of unique spatial arrangements is the important bit - and that remains the same.

My memory is misty over these compounds because it's been decades since I looked at them - but my bad!

I guess positional isomer of Pub 105 would technically be the term. I always ask the same thing - have these compound been tested in man?
 
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Oh yeah - then you have conformers (which you can only visualize in 3D) as well as tautomers, zwitterions and mesoionics all of which aren't readily drawn as a single 'diagram' as they incerconvene between two or more states BUT all alter the stereochemical arrangement.

As a final note, axial chirality (Atropisomerism) and helicity.

In short - it's quite complex.
 
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THE BIG 6: Just Taking You Back To Tha Old Skool!

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


mda
1-(3,4-methylenedioxyphenyl)-2-aminopropane

1-(3,4-methylenedioxyphenyl)-2-methylaminopropane.png


mdma
1-(3,4-methylenedioxyphenyl)-2-methylaminopropane

1-(3,4-methylenedioxyphenyl)-2-ethylaminopropane.png


mde
1-(3,4-methylenedioxyphenyl)-2-ethylaminopropane

1-phenyl-2-aminopropane.png


amp
1-phenyl-2-aminopropane

1-phenyl-2-methylaminopropane.png


meth
1-phenyl-2-methylaminopropane

1-phenyl-2-ethylaminopropane.png


eth
1-phenyl-2-ethylaminopropane

With the exception of maybe amp, as of 2025 most of the Big 6 are illegal as Hail.
 
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I've often wondered about the dynamics of diphenylaminopropane derivatives like β-Phenylmethamphetamine. Also, when I look at a compound like Ipazilide, I can't help but notice how much it kinda resembles LSD…

But wait so is Cypenamine a psychostimulant or a opioid painkiller? Both? I see things that indicate either one…
 
unodelacosa said:
This one, "BRUCE" and "PETER" remind me of the aminorex series. (Side note: All My Aminorexes Live In Reno, Texas is a live album I haven't recorded yet, but I digress.)

Point is: I'm willing to bet these are all likely active. What do you think? Hell there's even a very much active 3,4-methylenedioxyaminorex. Of course I'm talking about 2-amino-5-aryloxazolines.
Click to expand...
It'd Say Bruce And Peter Are Active, Yes.
 
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