Methcathinone peptide analogs

[paracelsius]

this from pubchem db:

This is a regulated substance. Complete access to the full Controlled Substances Squared application for 24 hours - Scitegrity database ....compound controlled in 7 jurisdictions

anybody knows which jurisdictions .. cant find any info anywhere on legal status of that one..

sure it looks like the equivalent of propylhexedrine/meth pair

for cathinones

with the aryl ring replaced by a piperidine..(sorry that stupid program likes to draw it upside down when switching from phenyl to piperidyl..but you got the point!

so is it analog laws jurisdictions they talking about?? or is it specifically scheduled?
any link for infos would be appreciated... thx

 

[clubcard]

Benzene and other aromatics are planer (flat). When cyclohexane replaces a benzene in (meth)amphetamine or bk-PEA, potency is much lower. On a related topic, I have read stories of people making methamphetamine analogues with a 4-pyridine in place of the benzene. What the N: at the p would do, I don't know. I'm sure I read some BS on it being the same in some paper from the 90s. Pyridine won't undergo hydroxylation as readily so metabolism will be via the terminal alkane -CH3. Well, experience has taught me that a terminal -CH2F not only gets around the law but it also prevents THAT metabolic pathway. Just so people know, analogs with a -CH2F are less soluble so you need to check the phosphate & sulfate salt. In every case, one of them was soluble to make snorting practical.
Nitrocaine died because the lazy chemists insisted on making the hydrochloride addition salt and REFUSED to make the phosphate & sulfate. Anyone who has put nitrocaine on foil knows it works if smoked.

 

[Nagelfar]

yeah when a cyclohexane is present it's likely to twist and take other conformations, the arene benzene I think the word is planar, as described by the extra bonds and having a "π-symmetry". Though my chemical knowledge, being self-taught, has huge gaps in the otherwise mundane early level facts of chemistry, am I correct in having gleaned the benzene being alternatingly double-bonded, though effectively what's taking place as depicted, due to how it is sterically placed is more circular, and is what's meant by pi symmetry? Some use the 'circle' inside the cyclohexane to convey it being an arene.

 

[Skorpio]

Is that first compound a peptide? It does have an amide bond (piperamde?), but it isn't a polymer of amino acids.

Thread title got me excited for something way cooler tbh.

 

[paracelsius]

Benzene and other aromatics are planer (flat). When cyclohexane replaces a benzene in (meth)amphetamine or bk-PEA, potency is much lower....

yeah sure meth aromatic ring is planar but doesnt mean much in term of resulting pharmacological profile: propylhexedrine is about half potency of meth as reuptake inhbitor (similar to dextroAMPH) but more potent than meth as monoamines releaser(both 3) which is why it is more empathogen, much closer to mdma than meth.. I suspect the same with the OP compounds. replacing the alfa-methyl of OP with a propyl or butyl or pentyl or the Nmethyl with pyrrolidine will be even more potent.. but the question is why are this class scheduled? I have yet to find anything in literature (patent or general) about those..

yeah when a cyclohexane is present it's likely to twist and take other conformations, the arene benzene I think the word is planar,

only 3 conformations that are stable: chair (1), boat (4) and twisted (2&3) in that order of stability but depend really the specific molecule, but much of the time chair 1 is favored:

Is that first compound a peptide? It does have an amide bond (piperamde?), but it isn't a polymer of amino acids.

I guess it is a matter a semantic. yeah sure it is not a polymer of amino acids but a monomer of N-methyl-Valine...

Thread title got me excited for something way cooler tbh.

Would be pretty sexy to have polymer of amino acids (ie peptides or proteins) that are psychoactive SDRI/A.. but I am afraid polymers of aminoacids (peptides/proteins) make horrible drugs (pretty much zero bioavailability). Unless one is prepared to have intracranial injection straight to the brain limbic system to have the intended effect!.. but yeah would be nice to see useful peptides/proteins stim.

 

[Skorpio]

Would be pretty sexy to have polymer of amino acids (ie peptides or proteins) that are psychoactive SDRI/A.. but I am afraid polymers of aminoacids (peptides/proteins) make horrible drugs (pretty much zero bioavailability). Unless one is prepared to have intracranial injection straight to the brain limbic system to have the intended effect!.. but yeah would be nice to see useful peptides/proteins stim.

All those 2040 junkies will be absolutely squirming for intrathecal dope pumps. I bet if that took off it wouldn't be too hard to use beta endorphin or enkephalin as decent leads.

I guess it is a matter a semantic. yeah sure it is not a polymer of amino acids but a monomer of N-methyl-Valine...

I don't really see that either. I see the n methyl but there is nothing at the alpha carbon (that line could be a thin methyl group I guess) but thy makes it like n methyl piperido glycine/alanine (I'm making this name up for a saturated 6 member amide ring. Fuck iiupac). (valine has an isopropyl group on the alpha carbon).

A monomer of n methyl valine would look like this

N-Methylvaline | C6H13NO2 | ChemSpider

Structure, properties, spectra, suppliers and links for: N-Methylvaline, 2566-32-7.

www.chemspider.com

 

[Nagelfar]

only 3 conformations that are stable: chair (1), boat (4) and twisted (2&3) in that order of stability but depend really the specific molecule, but much of the time chair 1 is favored:

I understand binding can favor one conformation over another, and additions can make one position more likely. The tropane ring system is similar, and various phenyltropanes diverge from the more common conformations.

 

[4meSM]

yeah when a cyclohexane is present it's likely to twist and take other conformations, the arene benzene I think the word is planar, as described by the extra bonds and having a "π-symmetry". Though my chemical knowledge, being self-taught, has huge gaps in the otherwise mundane early level facts of chemistry, am I correct in having gleaned the benzene being alternatingly double-bonded, though effectively what's taking place as depicted, due to how it is sterically placed is more circular, and is what's meant by pi symmetry? Some use the 'circle' inside the cyclohexane to convey it being an arene.

Correct, the benzene ring is planar because it's an aromatic system. Hypothetically speaking the benzene ring could adopt other non-planar conformations, but that doesn't happen because the aromatic conformation is infinitely more stable than all the other "possible" ones, so the ring stays aromatic.


For aromaticity to take place, the system needs to allow for the delocalization of its π-electrons. And that only happens when the 6 π-orbitals are parallel to one another, and perpendicular to the C-C bonds. Those π-orbitals also need to be in the same "phase".

It's just that π-orbitals have 2 symmetric lobes, usually represented by a + and - or by different colors (black and white) as a convention. Being in-phase just means that all the black lobes are on the same side and vice versa for the white lobes, as seen bellow. So the electrons can move freely from one orbital to the other, and so on.

This is all possible thanks to being a cyclic molecule, and having 3 alternating double bonds (6 π electrons), so: simple-double-simple-double-simple-double. Said alternation, between simple and double bonds, is called conjugation.
By the way, each double bond has 2 π electrons.

The formula (π-2)/4 from Huckel's rule can be used to determine if a cyclic (conjugated) molecule is aromatic. You replace π with the number of conjugated π electrons, if the result is an positive integer then the system is aromatic.

So for benzene: (6-2)/4 = 1 which is a positive integer <=> aromatic <=> planar

To understand why orbitals have 2 lobes, and why there are bonding and anti-bonding components to all molecular orbitals, one would have to read a bit about orbital molecular theory, particularly the "linear combination of atomic orbitals (or LCAO)" approach. I don't have the skills to explain it properly lol.

 

[Nagelfar]

…the system needs to allow for the delocalization of its π-electrons. …Those π-orbitals also need to be in the same "phase".

…Being in-phase just means that all the black lobes are on the same side and vice versa for the white lobes, as seen bellow. So the electrons can move freely from one orbital to the other, and so on.

…
To understand why orbitals have 2 lobes, …

Do you know whether the electrons are shared between the plane above and the plane below, or contrary to that do each set of electrons "stay on their own plane";

…or is the above an utter nonsensical question, being that in–fact the electron exchange takes place inside the faces of the ring, between the lobes?

Does the crossing between the 'orbitals' just mean of 'the same phase', as it were, or are the electrons responsible for the phases? (probably more of a question of atomic physics than molecular)

 

[4meSM]

Do you know whether the electrons are shared between the plane above and the plane below, or contrary to that do each set of electrons "stay on their own plane";

…or is the above an utter nonsensical question, being that in–fact the electron exchange takes place inside the faces of the ring, between the lobes?

Does the crossing between the 'orbitals' just mean of 'the same phase', as it were, or are the electrons responsible for the phases? (probably more of a question of atomic physics than molecular)

In this case orbitals just help us figure out the area where the corresponding electron may be, it's based on probability. For example those π-orbitals (and all p orbitals in general) are shaped like an infinity sign, which means the electron is likely to be on the area filled by one of the 2 symmetrical lobes (equal probability between the 2 IIRC) but you will almost never find it in the intersection between the 2 lobes.

Since all electrons are indistinguishable and interchangable I don't think you could say one particular electron stays on its plane, you might write it like that if you're trying to describe the system but in reality you could never tell if 2 electrons have interchanged their positions (sneaky bastards).

So I believe one electron may go from one side of the ring to the other, but it probably doesn't pass through the interception between the 2 planes. It's just in one of the 2 red circles:

How did the electron cross the road? No fucking idea...

 

[Nagelfar]

^pretty much like quantum tunneling.

That's good on me then: my first assumption was that they were all on either side and I was all about to post the question when I had doubt at the last moment and edited it before I posted in the case that the electrons were somehow on the plane with the carbon atoms. Glad to know my instincts were correct and I needn't have doubted myself.

 

[Gaffy]

Benzene and other aromatics are planer (flat). When cyclohexane replaces a benzene in (meth)amphetamine or bk-PEA, potency is much lower. On a related topic, I have read stories of people making methamphetamine analogues with a 4-pyridine in place of the benzene. What the N: at the p would do, I don't know. I'm sure I read some BS on it being the same in some paper from the 90s. Pyridine won't undergo hydroxylation as readily so metabolism will be via the terminal alkane -CH3. Well, experience has taught me that a terminal -CH2F not only gets around the law but it also prevents THAT metabolic pathway. Just so people know, analogs with a -CH2F are less soluble so you need to check the phosphate & sulfate salt. In every case, one of them was soluble to make snorting practical.
Nitrocaine died because the lazy chemists insisted on making the hydrochloride addition salt and REFUSED to make the phosphate & sulfate. Anyone who has put nitrocaine on foil knows it works if smoked.

Nitracaïne never was a thing, Just as dimethocaine, which is still better. I'vr had both, they just aren't good

 

[t_wrex]

Concerning propylhexedrine, would adding double carbon bonds to the ring confer more stability to the compound? e.g., a cyclohexenyl or cyclohexadienyl ring instead of a cyclohexane? Would these even be possible to make?

 

[Gaffy]

I expexted protein like compounds that act like methcath...

 

[clubcard]

Well aromatic rings act as hydrogen bond acceptors. They are also lipohilic so generally they fit into a lipophilic pocket.