• N&PD Moderators: Skorpio | thegreenhand

  • Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

I Like to Draw Pictures of Random Molecules

Status
Not open for further replies.
JacksinPA said:
You have the structure wrong for this molecule. See https://psychonautwiki.org/wiki/Cyclazodone. You've drawn it with the side group as oxetan-3-amine rather than cyclopropyl amine. It's also said to be hepatotoxic. Here is the correct structure for cyclazodone:
Cyclazodone.jpg


I did a brief Google search & see it available as a 'research chemical'. Caveat emptor.
Click to expand...

This thread is titled "draw pictures of random molecules" - in case you haven't noticed, the 4-fluorophenyl group doesn't exist in Cyclazadone either :p

I draw a different molecule which "might increase fun & potency" (compared to, yes, Cyclazadone!).
 
Fluorine & novel side chain or not, pemoline & likely its derivatives are nothing to play around with except to draw. See: Liver toxicity In some patients pemoline is suspected of causing hepatotoxicity,[8] so the FDA recommended that regular liver tests should be performed on those treated with it.[9] Since receiving FDA approval in 1975,[10] it has been linked with 21 cases of liver failure, of which 13 resulted in liver replacement or death.

In March 2005 Abbott Laboratories and generic manufacturers withdrew pemoline from the American market due to concerns about the liver toxicity risk.[11] See https://en.wikipedia.org/wiki/Pemoline Perhaps fun & potency before you die of liver failure.

Regarding cyclazodone:
toxicity and harm potential

The toxicity and long-term health effects of recreational cyclazodone use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown. This is because cyclazodone has a very limited history of human usage.
There exists a history of liver failure in children taking the structurally related compound pemoline[8], which resulted in its removal from the market. Another compound related in structure, 4-methylaminorex, has been associated with pulmonary hypertension[9]; though, it is reported to induce far stronger stimulation than that of cyclazodone. While cyclazodone is 5-10x more potent than pemoline, it is not known if it possesses the same level of hepatoxicity.
In rodents and primates, sufficiently high doses of monoamine releasing agents cause dopaminergic neurotoxicity, or damage to dopamine neurons, which is characterized by reduced transporter and receptor function. There is no evidence that releasing agents are directly neurotoxic in humans. However, large doses of releasing agents may cause indirect neurotoxicity as a result of increased oxidative stress from reactive oxygen species and autoxidation of dopamine.[citation needed]
It is strongly recommended that one use harm reduction practices when using this substance.
Tolerance and addiction potential

Addiction is a serious risk with heavy recreational stimulant use but is unlikely to arise from typical long-term medical use at therapeutic doses. Notably, the structurally related compound pemoline fails to demonstrate a potential for self-administration in primates and is considered to have reduced risk of dependence relative to those more typical dopaminergic stimulants. Caution is nonetheless advised, as with other monoamine releasing agents.
Tolerance to many of the effects of cyclazodone develops with prolonged and repeated use. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about 3 - 7 days for the tolerance to be reduced to half and 1 - 2 weeks to be back at baseline (in the absence of further consumption). Cyclazodone presents all dopaminergic stimulants, meaning that after the consumption of amphetamine all stimulants will have a reduced effect.
Psychosis

Main article: Stimulant psychosis
Based on its pharmacological similarity to other stimulants, it is likely that misuse of this compound can result in state of psychosis marked by a variety of symptoms (e.g., paranoia, hallucinations, or delusions).[10][11] A review on the treatment for amphetamine and methamphetamine abuse-induced psychosis states that about 5–15% of users fail to recover completely.[11][12] The same review asserts that based upon at least one trial, antipsychotic medications effectively resolve the symptoms of acute amphetamine psychosis.[11] Psychosis very rarely arises from therapeutic use. The combination of the prolonged use of high doses combined with sleep deprivation significantly increases the risk of stimulant psychosis.[
https://psychonautwiki.org/wiki/Cyclazodone
 
Last edited:
26f93JP.png


can anyone tell me what dangers would arise from something like this?

I was thinking the Br would leave the magnesium pretty easily, which could brominate things that shouldn't be brominated. Is there more to it?
Click to expand...

Grignard reagents are strong bases, they are incompatible with proton-bearing groups (-OH, -NRH or -NH2, -SH) and anything that's even slightly acidic will end up converting R-Mg-X to R-H and Mg(OH)X where X=Cl, Br, I.

So unless you had protected the amine as a phthalimide or something the Grignard would not be formable. And even if you could form it, working in anhydrous ether solvents (ethyl ether and THF are two common ones) is mandatory, with dry glassware and a stream of N2 or argon purging any moisture and oxygen out.
 
Yeah JacksinPA, Pemoline itself is a metabolite of Levamisole iirc. Certainly not one suited for regular use.

Back on topic:

methyl%20N-(1%2C2-diphenylethyl)carbamate.png
 
Roi

Does this have a trivial or non-commercial name besides its chemical name(s)? I don't recognize it off hand but carbamates are known to be carcinogenic & mutagenic.
 
AM4054.jpg


Potent CB1 agonist. There were 2 errors in the earlier drawing which I have corrected.
 
Last edited:
JacksinPA said:
What you've drawn is called a Grignard Reagent. Firstly, it couldn't exist as you've drawn it because the Ar-Mg-Br would react with the free amine on the end of the ethyl chain. I don't believe this would act as a brominating reagent even if you protected that amine first with groups that could be removed in a later step, like benzyl groups with can be removed via hydrogenation. I'm not familiar with any application of these reagents as brominating agents. There are simple, commercially available molecules like N-bromosuccinimide & even elemental bromine for doing that.

Grignard reagents are formed in solution of either dry ether or tetrahydrofuran & are not usually isolated but are reacted directly with things like ketones & aldehydes. With metal catalysis they can be made to couple with things like alkyl halides.

So yes, there is a lot more to it. Just being able to draw a structure doesn't mean it makes sense or can be made or exist in the real world.

I don't know what your educational background is in organic chemistry, but Grignard chemistry is usually first-year college organic 101. If you haven't already, order a good introductory organic textbook from Amazon or your local college bookstore. Or just read this: https://en.wikipedia.org/wiki/Grignard_reaction

Whatever you wind up doing, be very careful with Grignard chemistry. You're working with volatile & flammable solvents that have to be specially purified to remove peroxides & dried before using. The Grignard reaction itself, where magnesium metal reacts with the organic halide, are many times difficult to get started due to factors such as surface oxidation on the magnesium metal you are using. And once started, they can get pretty active, so you have to work under efficient reflux condensers for proper cooling. And most Grignard reactions are run under a continuous flow of dry nitrogen. Good luck!
Click to expand...

Ah, just learned in class today that there should be no protonated atoms like OH, NH, SH and so on with a Grignard Reagent. I wasn't actually planning on synthesizing any of this, I don't even know how -- I was just curious if it was even plausible since we went over the reaction in OChem.

Thanks for the insight!
 
aspiringdrugdesign said:
Ah, just learned in class today that there should be no protonated atoms like OH, NH, SH and so on with a Grignard Reagent. I wasn't actually planning on synthesizing any of this, I don't even know how -- I was just curious if it was even plausible since we went over the reaction in OChem.

Thanks for the insight!
Click to expand...

what makes the H on OH or SH different than the Hs connected to carbon atoms all througout the molecule? why don't those react while OH and NH2 do react? Always think about why something happens and you will ace organic chemistry.
 
For people thinking about NMDA antagonists, the spacial position of the basic amine's lone-pair is key. 8A-PDHQ has too many isomers so the metabolism could be complex so thumbs down. Dizocilpine has similar affinity but no DRI activity so isn't euphoric. The 1,2-diphenylethyl amines are non-rigid dizocilpine analogues. I cannot remember the 'magic angle'. I think it's 107.5? but this is thinking back 5 years. Dextrophan has the aromatic and 2 methylene spacer but seems too promiscuous. A French team took tiletamine, swapped cyclohexane for a 4-thiane and added an o-methyl. That obviously leads to 4 isomers but one was very potent indeed and who knows, maybe the sulphur is oxidised so by the time it reaches the bladder, it is inactive which may improve chronic bladder damage. It was published in a European (as a whole) periodical. They made a large set but both synthetic complexity and uncertainty of the metabolism of the 4 isomers (maybe you can racemize it so you just get the trans isomers?) made it another thumbs down. The space-filling methyl in dizocilpine may overlap the French set, who knows?

So, for the sake of keeping it real, the arylcyclohexyl (smaller and larger rings are inactive) and 1,2-diphenylethyl amines are the only 2 scaffolds worth tinkering. I DID wonder about affixing an extra carbon onto the 1,2-DEAs i.e. isopropyl but once again, isomers.....


I would appreciate someone confirming that angle. It was US research that discovered it,
 
LucidSDreamr said:
what makes the H on OH or SH different than the Hs connected to carbon atoms all througout the molecule? why don't those react while OH and NH2 do react? Always think about why something happens and you will ace organic chemistry.
Click to expand...

Well it'd be due to their relative electronegativities, right? Also I'd bet their pKa values impact how readily hydrogens are given up, and what is bonded to the carbons themselves.

What's that polymer looking thing with an opioid on it? Is that a delivery system?



mXNxAmS.png


Are there any alpha ketone phenethylamines with activity? I noticed modafinil and phenylpiracetam have this group (I know SARs don't work conveniently like that), and was curious if it had any certain role in binding to receptors
 
aspiringdrugdesign said:
What's that polymer looking thing with an opioid on it? Is that a delivery system?
Click to expand...

That "polymer thing" is a carbon nanotube, an extremely rigid carbon-based nanostructure. You've probably heard about this stuff already, and how it is supposed to be the wonder material of the future that we'll use to make anything from ultra-lightweight vehicles to computer circuitry to giant tethers for space elevators. I think LucidSDreamr was making a joke about wanting to inject his hydromorphone straight into the receptor :)
 
Last edited:
LucidSDreamr said:
^main lining is for pussies. main-receptoring is gonna be all the rage in the future
Click to expand...

Why stop at hydromorphone though? Reversible agonism? Pfffsh 8). If you truly want to get #redpilled (redneedled?), try CHLOROXYMORPHAMINE. This is oxymorphone with the 6-Oxo group replaced by a bis-chloroethylamine group, better known as "nitrogen mustard", a type of military-grade blistering agent and cytotoxic chemotherapy drug. In other words, you're irreversibly gluing that opioid into the receptor through chemical warfare.
313px-Chloroxymorphamine.svg.png
 
Last edited:
I can't find any reference to methyl (1,2-diphenylethyl)carbamate. Is this a known molecule or something you are just interested in?
 
Status
Not open for further replies.
Top