R57 (Stranger)
01-23-02 04:54
No 259833
      Silicon amphetamine???  Bookmark   

A bit of a wild idea but anyway...does anyone know if it would bee possible to incorporate a silicon atom in a benzene ring? (ie replace a carbon to make C5 Si H6). Coz then we could make silicon amphetamine, and if it worked it would be legal(at least in Europe!)laugh
 
 
 
 
    PrimoPyro
(Hive Prodigy)
01-23-02 05:25
No 259840
      Re: Silicon amphetamine???  Bookmark   

Interesting idea. I do not know enough chemistry to answer your question, but I am curious as well. Remember that silicon chemistry is only similar to carbon chemistry, not identical.

As for incorporating it into the ring, that's not really economic. There is nowhere to buy such a ring, and if you can synthesize a custom benzene ring, you can synthesize a standard one. Therefore, just buy aliphatic reagents and make rings of them.

But perhaps a silicon atom in the propyl chain? Or in place of the methylamine carbon?

Hmmm, silenation of catechol with SiH2Cl2? laugh Does that even exist?

Interesting.

                                                      PrimoPyro

Vivent Longtemps la Ruche!
 
 
 
 
    malvaxman
(Hive Bee)
01-23-02 05:29
No 259842
      Re: Silicon amphetamine???  Bookmark   

It would be legal yes. I would rather go for incorporating nitrogen. You maybee would like be the first to try?
It does“nt sound to helthy to have silicone in the blood.. Are there any substances in the human body with silicone?
(Tit-filling not counted)smile
 
 
 
 
    PrimoPyro
(Hive Prodigy)
01-23-02 05:49
No 259846
      Re: Silicon amphetamine???  Bookmark   

Silicon not Silicone. One is an element, the other a carbonic polymer.

I think there was a debate about nitrogen being too polar to sub as anything but nitrogen.

                                                     PrimoPyro

Vivent Longtemps la Ruche!
 
 
 
 
    R57
(Stranger)
01-23-02 06:51
No 259859
      Re: Silicon amphetamine???  Bookmark   

Well I know phenethyltrichlorosilane is available, maybe if this could bee somehow turned into P2P with the SiH3 instead of the Methyl group...any ideas?
 
 
 
 
    Rhodium
(Chief Bee)
01-23-02 07:40
No 259869
      Re: Silicon amphetamine???  Bookmark   

You cannot have any free Si-H bonds on a compound that is supposed to be stable in air, it spontaneously reacts with oxygen. A more interesting avenue to explore would be F atoms substituted for oxygen just anywhere on the molecule.
 
 
 
 
    PrimoPyro
(Hive Prodigy)
01-23-02 08:26
No 259890
      Re: Silicon amphetamine???  Bookmark   

But how would one incorporate Fluorine into a compound like methamphetamine, where there are no oxygen atoms to substitute for? You would have to add onto the ring and such.

But for MDMA and other analogs, I like the idea. Fluorine will form two bonds like oxygen? Is coordinate valency at work to accomplish this?

                                                    PrimoPyro

Vivent Longtemps la Ruche!
 
 
 
 
    hest
(Hive Bee)
01-23-02 09:24
No 259904
      Re: Silicon amphetamine???  Bookmark   

The carbon annalog og E shuld act the same way as the real stuff
 
 
 
 
    Rhodium
(Chief Bee)
01-23-02 09:36
No 259909
      Re: Silicon amphetamine???  Bookmark   

Fluorine forms only one bond, just like all the other halogens.

To incorporate it into the ring, start with a fluorinated benzaldehyde, and to add it to the side chain, fluorinate ephedrine (1-fluoro-meth) or methcathinone (1,1-difluorometh), or phenylalanine could be reduced to phenylalaninol, and the terminal alcohol fluorinated to give alpha-fluoromethylamphetamine (which can be methylated). Alkylating P2P with fluoromethylformamide would give N-fluoromethylamphetamine. The possibilities are endless, and all compounds are legal, as long as they aren't sold for human consumption.

Most of them should have VERY similar pharmacology to methamphetamine.
 
 
 
 
    R57
(Stranger)
01-23-02 11:37
No 259963
      Re: Silicon amphetamine???  Bookmark   

Thanks Rhodium!smile I knew my plan would be too good to bee true but fluorination sounds just as fun! Would chlorination/bromination work as well? I wouldnt fancy messing around with fluorine it sounds a bit nasty... As for :
           all compounds are legal, as long as they aren't sold for human consumption
Ah, if only. We have different laws in the U.K - any compound structurally based on phenethylamine, with  substitution in the ring by alkyl, alkoxy, alkylenedioxy(sob) or halide substituents is illegal to manufacture! According to the Misuse of Drugs Regulations 1985. Grr.mad
 
 
 
 
    Rhodium
(Chief Bee)
01-23-02 12:02
No 259970
      Re: Silicon amphetamine???  Bookmark   

No, chlorine/bromine would change the pharmacology of the compound too much, and possibly even make the compound toxic. Organic fluorides are unreactive an in many ways similar to hydrogen, that's why substitution may work in this case.
 
 
 
 
    R57
(Stranger)
01-23-02 12:31
No 259980
      Re: Silicon amphetamine???  Bookmark   

Ah I see. But alpha-fluoromethylamphetamine still sounds good...all the precursors seem OK - but for fluorination do I need fluorine gas? Or is there a fluorine equivalent to SOCl2/POCl3 to replace the OH group?
 
 
 
 
    Rhodium
(Chief Bee)
01-23-02 14:40
No 260026
      Re: Silicon amphetamine???  Bookmark   

Yes, DAST (dimethylaminosulfur trifluoride) is a very good alternative, it can be handled inside a fume hood, as opposed to a glove box. Do a websearch, and you'll find application examples.
 
 
 
 
    slappy
(Hive Bee)
01-24-02 04:09
No 260312
      Re: Silicon amphetamine???  Bookmark   

Silabenzene has been made and studied, problem is, it has only been made by flash thermolysis and studied by UV spectrosopy in the gas phase, or by matrix isolation at <80°K.

The problem with incorporating a Si atom into an aromatic ring is a larger one. First, there is distortion due to the larger radius of silicon, the longer C-Si bond length (~25% longer), and second, the C-Si bond energy is ~10kcal/mol less than C-C due in part to Si's increased electrophilicity. (In benzene, all of the C-C bond lengths are the same 1.4A)

A Si analouge of benzene is not truly aromatic. Aromatic (=delocalized pi systems with a continuous p-orbital overlap) sytems are usually planar rings, this due to the carbons sp2 hybridization. The thing is, Atomic Orbital hybridization is pretty much exclusive to the second row elements. This is due to the fact that the 2s & 2p orbitals occupy the same area of space, so that an electron can actually be in the 2s & a 2p orbital at the same time. This due to the unique shape of the 2s orbital which has a node in the center which pushes it farther out. This is due to pauli repultion from the core electrons in the 1s orbital. Third row main group elements such as Al, Si, P & S mainly use their 3p orbitals in bonding (They do have a d-orbital, but it does not participate in bonding). The 3p orbitals do not share the same area of space with the 3s, so hybridization does not occur. There is still p-orbital overlap between the sp2 C's and Si, but due to Orbital effects explained above the Si exhibits weak multiple bond character. It also usually (=not cyclic) adopts a trans-bent geometry due to decreased bonding angles as you go down the Group 14 elements.

On another note...

Perfluoroamphetamine would be fun! It would be volatile as hell, so you wouldn't even have to smoke it, just open the bottle and breath! Perfluoro hydrocarbons are generally pretty inert biologically. Safe, alot are being used in medicine and other fields.
 
 
 
 
    R57
(Stranger)
01-24-02 12:36
No 260423
      Re: Silicon amphetamine???  Bookmark   

Yeah, I had wondered about the longer Si-C bonds but I never thought about hybridisation. Thanks very much for explaining that to me Slappylaugh. I'm still dreaming about the fluoroamphetamine, because DAST is pretty expensive(£100/$160ish for 25g!!!)and until I get unhindered access to a fume hood I don't fancy messing around with it - if you've seen the MSDS you'll know what I mean...
 
 
 
 
    Rhodium
(Chief Bee)
01-24-02 14:01
No 260448
      Re: Silicon amphetamine???  Bookmark   

Begin here: ../rhodium/chemistry /fluoroamphetamine.html

No toxic fluorine chemicals, and an interesting result.
 
 
 
 
    yellium
(Hive Addict)
01-24-02 14:16
No 260458
      Re: Silicon amphetamine???  Bookmark   

But what about a 2,5-dimethoxy-4-silylsomething-phenethylamine?
 
 
 
 
    Rhodium
(Chief Bee)
01-24-02 14:41
No 260476
      Re: Silicon amphetamine???  Bookmark   

The only unreactive thing with a silicon on it that you could stick to the 4-position would be trimetylsilyl (Me3Si-), and as tert-butyl-dimethoxyamphetamine is (probably) inactive (or at least not very active), this probably is too, unfortunately. The 4-position is very sensitive to steric bulk.

I just can't get how all the 2C-G's can be so active when tert-butyl-dimethoxyamphetamine is not. Any ideas?