4-isopropylamphetamine

[LabRatNW]

Any substance that has a lone substitution para- to the ethylamine or sec-propylamine chain tend to create nasty metabolites or cause heart problems because of the way they interact with the serotonin system.

 

[Rectify]

Not quite.

 

[IHateOpiophobes]

i was just thinking about it, BL, do you think this could be active? any ideas? bioessays? potency? or is it a stupid idea, if yes, why? tell me what you think about it!

Formula:

Possible...I think it would be reactive, but getting across BBB might be problem, but the three Pi bonds of benzene in the circular movement make those electrons fairly available. One of the reasonance structures would be a carbanion which is extremely reactive, even though the second poster was correct about being on a tiertiary carbon which would increase stability greatly so....

I guess I haven't answered your question, need more info, look at other amphetamine backbone structures and compare.

so the extra 2 carbon groups and their position. You should lose polarity on the Isopropyl group due to cancelling dipole forces.

Interesting...

 

[IHateOpiophobes]

interesting.

Possible...I think it would be reactive, but getting across BBB might be problem, but the three Pi bonds of benzene in the circular movement make those electrons fairly available. One of the reasonance structures would be a carbanion which is extremely reactive, even though the second poster was correct about being on a tiertiary carbon which would increase stability greatly so....

I guess I haven't answered your question, need more info, look at other amphetamine backbone structures and compare.

so the extra 2 carbon groups and their position. You should lose polarity on the Isopropyl group due to cancelling dipole forces.

Interesting...

Thinking about it, aminating one of the terminal carbons making amphet-p-amine, probably would be like heroin, di-actyl-morphine. Just two highly lipid soluable groups increasing potency and entry through the BBB into the brain. Not sure about the numbers I cant see the molecule from reply field. Chirality is an amazing concept. It might do nothing at all.

 

[Hammilton]

Why would it possibly make it harder to cross the bbb? It should be more lipophillic ie less polar and capable of crossing even easier than the parent.

No?

 

[Smyth]

what if u had 2 (diametrically opposed) 2-aminopropane chains attached to a single benzene ring.

I.e. 1,4-bis-substituted

Chemdraw name: 1,1'-(1,4-phenylene)dipropan-2-amine.

 

[MurphyClox]

Possible...I think it would be reactive, but getting across BBB might be problem [1], but the three Pi bonds of benzene in the circular movement make those electrons fairly available. One of the reasonance structures would be a carbanion which is extremely reactive, even though the second poster was correct about being on a tiertiary carbon which would increase stability greatly so....

I guess I haven't answered your question, need more info, look at other amphetamine backbone structures and compare.

so the extra 2 carbon groups and their position. You should lose polarity on the Isopropyl group due to cancelling dipole forces.

Interesting...

[1] Absolutely NOT. Amphetamine readily crosses the BBB and the presented p-propan-2-yl-derivative is even more lipohilic.

blue marked parts MAN! Do you even know what you are talking about?! Please elaborate what you wanted to point out, otherwise I can call your post plain bullshit. No offense intended, but it makes absolutely NO sense!*)

- Murphy


*) From both the pharmacological and chemical point of view!

 

[vecktor]

Lol ^

 

[Rectify]

I don't hate opiates, I just don't personally like large doses b/c they make me sick.

 

[MurphyClox]

what if u had 2 (diametrically opposed) 2-aminopropane chains attached to a single benzene ring.

I.e. 1,4-bis-substituted

Chemdraw name: 1,1'-(1,4-phenylene)dipropan-2-amine.

The idea in general is not this bad. I remember to have read that some GPCRs (just as one example) occur naturally as functional dimers. IIRC, there was some work about dimeric dopaminergic ligands that showed biological activity surpassing the one of plainly 2 times the monomer. And wasn't there some evidence that these dimers seem to be the predominant form, at least with GPCRs?! Damn, have to check my notes...

Anyway, if one intends to use Smyth's proposed molecule as some kinda dimeric ligand, I'm convinced that the intermediate linker has to be significantly longer (several -CH2-groups).

If this was not the idea behind Smyth's post, I don't get what such a molecule should be good for...

- Murphy

 

[Riemann Zeta]

1,1'-(1,4-phenylene)dipropan-2-amine

This is a profoundly wacky molecule....mesophetamine would be an appropriate name. However, if we put aside the coolness of having a symmetric molecule and think about activity: I cannot see how it could ever be a decent DAT/NET substrate--large steric bulk at the 4-position quickly drops affinity toward the DAT, with a traditional increase toward the SERT. Thinking the the 4-isopropyl-amphetamine mentioned above, considering the 1:1:1 DAT:SERT:NET affinity ratio of 4-methylamphetamine, I'm betting it is quite serotonergic.

 

[Hammilton]

Yeah, I don't think from a SAR standpoint mesophetamine is likely to be a winner as a stimulant, but might make for a decent serotonergic neurotoxin.

I think the structures Murphy talks about were more along the lines of bis(1-phenylpropan-2-yl)amine, but I may be off my rocker a bit.

 

[nuke]

[1] Absolutely NOT. Amphetamine readily crosses the BBB and the presented p-propan-2-yl-derivative is even more lipohilic.

blue marked parts MAN! Do you even know what you are talking about?! Please elaborate what you wanted to point out, otherwise I can call your post plain bullshit. No offense intended, but it makes absolutely NO sense!*)

- Murphy


*) From both the pharmacological and chemical point of view!

I think he was saying that alkyl groups on benzene rings are electron withdrawing... except they're electron donating. Not that being electron withdrawing is necessarily a problem, either.

edit: Actually, rereading it, I'm really not sure what he's talking about.

 

[MurphyClox]

edit: Actually, rereading it, I'm really not sure what he's talking about.

Me neither. Therefore my post.

Sorry for the rude choice of words, but after reading this post I checked other contributions of this user, and had to notice that he constantly spreads blatant nonsense. Errors are indeed excusable (nobody is perfect, except maybe Vecktor ), but his posts read like a campaign for misinformation.

Not good, no Sir. (or Ma'am...)

- Murphy

 

[IHateOpiophobes]

Yes, that what I mean. Sorry if I wasn't clear. Receptors are protiens that work similar to the anti-body anti-gen idea. Charges on the protien receptors and the molecule and location of the drug determine affinity and potency. My guess is that it would make it easier to get across being so similar tooo meth. I was really tired last night.

What if the fact that the molecule is trans-not cis (assuming di-amine) changes everything. Maybe the new group is too bulky, maybe it's even absorbed quickly than methylated amphetamine alone. Let me know if you find any scientific articles or journals on isopropylamine.

I remember one poster saying something about nasty metabolitez, maybe he has some documentation.

I have "Wiley's (famous chem text author)" ORGANIC GUIDE TO DRUG SYNTHESIS" I'll look into it.

 

[Hammilton]

There doesn't seem to be any such book.

And Wiley isn't an author, it's a publishing house. I think you're talking about a book written by Daniel Lednicer, who is actually a member here, though I doubt he comes by often.

 

[vecktor]

What if the fact that the molecule is trans-not cis (assuming di-amine) changes everything. Maybe the new group is too bulky, maybe it's even absorbed quickly than methylated amphetamine alone. Let me know if you find any scientific articles or journals on isopropylamine.

which molecule are we talking about, I can't see any cis trans stuff going on here, the bonds are sp 3.