I Like to Draw Pictures of Random Molecules

[SKL]

4-MAR analogues anyone?

I only had access to 4-MAR once, and I have to say it was amazing, not very good for you apparently, but one of the few over-hyped drugs that lived up to the hype.

Stimulus properties of some analogues of 4-methylaminorex. - PubMed - NCBI http://www.ncbi.nlm.nih.gov/pubmed/7667356

4,4'-dimethylaminorex via EMCDDA (apparently this has circulated in Eastern Europe at least)

As suggested by another Bluelighter here, 2-flouro-methylaminorex?

2,4-dimethylaminorex? 4-ethylaminorex? (apparently some people have tasted this one)

 

[crmt28]

I'm not a specialist, but isn't that benzyl cyanide attached to the amine? I feel like this could have some toxicity issues. According to Wikipedia, benzyl cyanide produces hydrogen cyanide when burned.

(And trust me, people will try to smoke it)

 

[roi]

Not that many people smoke MDMA!

Attemppt at a sane potency fentanyl analogue with longer duration:

 

[neurotic]

i've been thinking about fentanyl too these last few days...

here's one based on carfentanil. just tweaked it a little in an attempt to stop obvious metabolic attacks. that bridge where it was the phenethyl was daring but who knows... carfentanil is pretty potent

 

[Dresden]

Not that many people smoke MDMA!

Attemppt at a sane potency fentanyl analogue with longer duration:

That looks something like Zantac.

 

[crmt28]

N,N-di(trifluoromethyl)tryptamine / N-methyl-N-trifluoromethyltryptamine
DTFMT / MTFMT.

Is that possible? I wonder why nobody ever tried to put any halogen in there. Fluroine seems small enough to me, but I'm no chemist.

 

[Dresden]

I don't know if those can exist or not, but these two sure could:

and

These next ones probably don't do anything much, but you never know. Possible alien neurotransmitters.

The Melatonin Series:

 

[Midnight Sun]

An effort to introduce the DET skeleton into LSD. I guess in a way it really isn't, though. More like EiPT if you ignore everything else. Random molecules right?

 

[Dresden]

It's hard to say without testing it, but the synthesis looks really really hard. It would have to be made from scratch if what I'm thinking is right. But I don't want to discuss synthesis of course.

I think this LSD analogue looks interesting though:

12-CF3-LSD.

On second thought, this one looks much yummier:

BAM! Note the DMT and MDMA pharmacophores in one molecule.

 

[aced126]

i've been thinking about fentanyl too these last few days...

here's one based on carfentanil. just tweaked it a little in an attempt to stop obvious metabolic attacks. that bridge where it was the phenethyl was daring but who knows... carfentanil is pretty potent

If the rigidified structure is in the correct binding conformation it could increase affinity by degrees.

 

[aced126]

I don't know if those can exist or not, but these two sure could:

Why do you think so? The aromatic nitrogen won't attack anything because the lone pair is involved in aromaticity isn't it? So just trifluoromethylation of the aliphatic amine.

 

[aced126]

BAM! Note the DMT and MDMA pharmacophores in one molecule.

Something makes me think this could block SERT really well.

 

[crmt28]

Uh, no idea what to call these tryptamine/phenethylamine hybrids. Inspired by lysergamide.

 

[Dresden]

Why do you think so? The aromatic nitrogen won't attack anything because the lone pair is involved in aromaticity isn't it? So just trifluoromethylation of the aliphatic amine.

I can't think of a reason why they couldn't exist, but I also haven't seen any before, and I've been at this for 20 years now. Like I said, I just don't really know for sure either way.

 

[Solipsis]

Isnt it because of the same reason why 2C-D with a chloro on the para methyl isnt stable?
I forgot the mechanism of degradation reactivity unfortunately..
Fluoro might be exception as leaving group.. Also its only with methyls apparently cause 2C-EF is a thing..

Am i way off here?

I might be confusing this with terminal halo or chloro alks being toxic..?

Or the fact that simply chlorinating 2C-D with UV light via radicals is unfortunately not a good idea..

Sorry to confuse..

I just thought something isosteric to 2C-E but analogous to 2C-D and 2C-C was a good idea..

: (

Edit:
Forget what i said : p
Apparently primary and secondary amines can be trifluoromethylated in good yield
using this 20b reagent:
http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-6-65

Protect the indole N first though right?

 

[pharmakos]

would you want that end of the molecule to be that electronegative?

 

[neurotic]

If the rigidified structure is in the correct binding conformation it could increase affinity by degrees.

where's clubcard when you need him

 

[aced126]

N indole doesn't need protecting I don't think, because the lone pair isn't available as a nucleophile because it is participating in forming the aromatic indole cloud. Halo alks could be toxic alkylating agents however the heavily electronegative trifluoro group should shield the carbon from nucleophilic attack. Furthermore fluorine is the worst halogen leaving group because it is so small, making it less able to delocalise the negative charge it gains if it leaves.

 

[belligerent drunk]

N indole doesn't need protecting I don't think, because the lone pair isn't available as a nucleophile because it is participating in forming the aromatic indole cloud. Halo alks could be toxic alkylating agents however the heavily electronegative trifluoro group should shield the carbon from nucleophilic attack. Furthermore fluorine is the worst halogen leaving group because it is so small, making it less able to delocalise the negative charge it gains if it leaves.

You're right about the nitrogen in the indole. It usually is protected though, just as a precaution, but normally it needs activation with a strong base (hydride for example) to deprotonate it, so the nucleophilicity is greatly increased (I hope I'm not going into synthesis discussion here, if I am, I apologize) for it to participate in a reaction. AFAIK trifluoromethyl moiety does not behave as an alkylating agent, and yes fluoride is the worst leaving group. Perfluoroalkanes are an interesting class of molecules, chemically very inert and typically not keen on interacting with anything.

 

[crmt28]

Silly bonus molecule.

N,N-Diperfluroisopropyltryptamine. (Tree-ptamine)