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    hest
(Hive Bee)
04-19-01 11:07
No 185131
      New Amph. more potent than LSD   Reply  
   
In J.Med.Chem. 2001,44, 1003-1010, there is an article abouth some very potent sub. amphetamines

The TM is this one (pic 1)

[

they both make the R form and the S form

For thr most potent form, the R form, the strenght is:

When x is H the A is a bit stronger than DOB
When x is Br the A is app. 10-20 times stronger than DOB
When x is CF3 the A is app. 5-10 times stronger than DOB

The S form of the TM has app. the ½ strenght of the R form (that's still a lot:)
The synt in the article start with l alanine, and introduce the opt.act. center from the beginning. Nice but hard to do at home. But if we start with this one, it become much easyer

[

All the steps is standardt chem.
The following steps should also bee posible

[

Mabye the bromination should bee the last thing to doo.

The oxidation with DDQ is also posible with NBS or Pd/C in wacum (dehydrogenation). It is this oxidation that makes the TM so potent, the non oxidated molecule has also been made (J.Med.Chem.1996,39,2953-2961)


Some bioassayes on human would bee nice, but i'l guess we have to do the hard work :-)
 
   
 
   
    Rhodium
(Chief Bee)
04-19-01 20:43
No 185224
 
      Re: New Amph. more potent than LSD   Reply  
   
Great find!

The bromination cannot be done as the last step, or the furan rings will be brominated. Are all the steps in the synth of the benzo-bisdihydrofuran in the article? It seems a lot better than their original synth using bromochloroethane and BuLi...
http://rhodium.lycaeum.org/
 
   
 
   
    hest
(Hive Bee)
04-19-01 21:32
No 185229
      Re: New Amph. more potent than LSD   Reply  
   
Yes. all the steps is in the article, if 'the beehive' wants it i'l make a nice writup after the weg.
 
   
 
   
    savestheday
(Hive Bee)
04-20-01 00:37
No 185262
 
      Re: New Amph. more potent than LSD   Reply  
   
Very interesting...
anymore information would be greatly appreciated. Shulgin doesn't mention anything close to this?
 
   
 
   
    Lilienthal
(Moderator)
04-20-01 03:08
No 185293
      Re: New Amph. more potent than LSD   Reply  
   
See also Post No 122784 for a previous discussion on this topic smile.
 
   
 
   
    yellium
(Hive Bee)
04-20-01 06:13
No 185323
      Re: New Amph. more potent than LSD   Reply  
   
Another question is whether it is an interesting compound. F'r instance, the 2C-G compounds are not that potent, but they are very long lasting and don't seem to be very much `fun', compared to other compounds. 
 
   
 
   
    moo
(Stranger)
04-20-01 19:56
No 185431
      Re: New Amph. more potent than LSD   Reply  
   
But then again, receptor binding and resistance to metabolism are two different stories. The reports on DOTFM make me scared.
understanding is everything
 
   
 
   
    Rhodium
(Chief Bee)
04-21-01 01:07
No 185476
 
      Re: New Amph. more potent than LSD   Reply  
   
Everybody refers to scare stories with DOTFM, but I have never heard the actual stories. Tell me? Dosage, duration, effects?
http://rhodium.lycaeum.org/
 
   
 
   
    moo
(Stranger)
04-23-01 20:17
No 186117
      Re: New Amph. more potent than LSD   Reply  
   
It should have said "rumours". I'm referring to what drone told, but cannot be sure. I bet certain researchers we all know could provide more information on the subject.
understanding is everything
 
   
 
   
    hest
(Hive Bee)
04-25-01 06:08
No 186514
      Re: New Amph. more potent than LSD   Reply  
   
The fist step is posible, but i gues i'll have to tune it a bit :-)
[
The reaction was made in boiling methanol with NaOH as the base, reactiontime 2 h yeald 20% (yak)
I will try some other solvents and a longer reaktionstime
 
   
 
   
    Rhodium
(Chief Bee)
04-25-01 22:31
No 186707
 
      Re: New Amph. more potent than LSD   Reply  
   
Perhaps you should try using 2-bromoethanol instead of chloroethanol? Boiling ethylene oxide in 48% HBr should produce 2-bromoethanol. KOH is probably better than NaOH too.

Have you looked up any journal references on the synthesis of your product? It would probably help alot. 
http://rhodium.lycaeum.org/
 
   
 
   
    Osmium
(Stoni's sexual toy)
04-25-01 23:53
No 186728
      Re: New Amph. more potent than LSD   Reply  
   
In the older ref about this class of compounds they used 1,2-bromo-chloro-ethane, or 1,2-bromo-iodo-ethane, and had higher yields.
 
   
 
   
    Rhodium
(Chief Bee)
04-26-01 12:52
No 186901
 
      Re: New Amph. more potent than LSD   Reply  
   
Yes, but considering the price of bromochloroethane, and the special handling of the required BuLi in the former procedure, this alternative sounds better for most of us.
http://rhodium.lycaeum.org/
 
   
 
   
    hest
(Hive Bee)
04-29-01 05:51
No 187650
      Re: New Amph. more potent than LSD   Reply  
   
Disolve 6,16g(110mmol) KOH in 60mL wather, let the wather cool down ( 30°C), then add 5g(45mmol) hydroquinon and 8,85g(110mmol) 2-chloro-ethanol. Reflux the solution for 12 houers, cool it down (with ice) filter off the raw product.
Disolve the raw product in 100mL hot EtOAC, ekstract with 3*30mL 2M NaOH, dry the EtOAC with MgSO4, and remove the solvent in vaco.
yeald 3,5g (40%)
pure on TLC (Rf 0,44 with EtOAC as the solvent)
The same eksp. was done with 10g hydroquinon, and the yeald was again 40%

I think this is the way, the yeald is not high, but the starting materials is almost free.
I'll will now carye on withe the next step.
 
   
 
   
    yellium
(Hive Bee)
04-29-01 08:49
No 187690
      Re: New Amph. more potent than LSD   Reply  
   
Do you dare to ingest the final product?

 
   
 
   
    smiley_boy
(Hive Bee)
04-29-01 13:47
No 187760
      Re: New Amph. more potent than LSD   Reply  
   
The thing that sticks out in my mind about this is that the bromo-substituted analog is more potent in this series than its trifluoromethyl counterpart. I didn't see any discussion on this point in the paper, but it certanly warrants some sort of comment. Curious.
 
   
 
   
    hest
(Hive Bee)
04-29-01 21:30
No 187845
      Re: New Amph. more potent than LSD   Reply  
   
yellium- This might bee the new kitchen table 'lsd' synthesis (simple (compared to lysergacid) to manufacture, stabel product and strong enough to distribute at blotters). I think i'll firs try the phenetylamin, and a methoxy group instead of the Br would proberly make the product lighter and easyer for the metabolism to degrade.
 
   
 
   
    yellium
(Hive Bee)
04-29-01 21:47
No 187849
      Re: New Amph. more potent than LSD   Reply  
   
And without any substituent you also have a pretty active compound.
 
   
 
   
    weasil
(Hive Bee)
04-30-01 07:24
No 187933
      Re: New Amph. more potent than LSD   Reply  
   
NO, I strongly demand you to only produce the brominated product. To do otherwise would be undermining my authority.
 
   
 
   
    Rhodium
(Chief Bee)
05-11-01 10:26
No 193388
 
      Re: New Amph. more potent than LSD   Reply  
   
A VERY useful reference for the synthesis of the molecule below can be found in the journal Huaxue Shiji 15(4), 246-247 (1993). Unfortunately, I have no idea at all where to find that journal, or in what language it is written. Damn CAS Online, I don't want to be reminded of excellent reactions which are located in unreachable journals.


http://rhodium.lycaeum.org/
 
   
 
   
    dildoque
(Newbee)
05-11-01 19:22
No 193458
      Re: New Amph. more potent than LSD   Reply  
   
I found something:

Huaxue-shiji (Chemical Reactions) : shuangyuekan / Huaxue-shiji Bianjibu bianji. - Beijing : Huaxue Huaxue Shiji Keji Qingbao Zhongxinzhan, 1979-
ISSN:  0258-3283

smile
 
   
 
   
    hest
(Hive Bee)
05-24-01 03:02
No 196477
      Re: New Amph. more potent than LSD   Reply  
   
Subject: Re: New Amph. more potent than LSD
Well, the chlorination of the alcohol was not that easye. Boiling it with SOCl2 for 12 h. did nothing. Guess you hawe to use pyridine as well ( they doo that in the article )
But i can't stand the smell, so this was the next idea

[

It works werrye well.
Here is the cookbok

A mixture off 11g(0,1mol) hydroquinone, 16g(0,4mol) NaOH in 80mL wather was mixet with 2,2g(0,001mol) Benzyltriethylammoniumchlorid and 0,52g NaHSO3 in 80mL 1,2dichloroethane. The mixture was refluxet for 12 houers, made acid with HCl(aq). The org layer was sep. from the wather and the 1,2-DCE was removed in wac. The solid mass was then rextalised from ethanol (250mL)
Yeald app. 80%.
Pure on TLC Rf 0,68 1:1 ether:petr.ether
The org. phase is a 'mudy' one, but thats ok.

The ammonium compound is a phase transpher catalyst. almost anny org ammonium salt works, (tetrabutylammoniumbromid and so on) It should also bee posible to doo the reaction without the PTC.
the NaHSO3 makes the hydroquinone more stabel, but is not a must.
Some refs
Synthesis 1988 p.950-952
Cannadian j.chem. 1955 p.1442-1447 (withouth PTC) 


 
 
   
 
   
    Rhodium
(Chief Bee)
05-24-01 03:41
No 196490
 
      Re: New Amph. more potent than LSD   Reply  
   
Is this procedure from an article, or from SWIM's own experience? I don't get why the hydroquinone only reacts with the dichloroethane, and not with any 2-chloroethoxyphenyl-something forming di/polymers? Is it due to the large excess of DCE? Why the NaHSO3, an antioxidant for the hydroquinone?
http://rhodium.lycaeum.org/
 
   
 
   
    hest
(Hive Bee)
05-24-01 03:54
No 196496
      Re: New Amph. more potent than LSD   Reply  
   
From swims own experience, but the ide is from the article in synthesis. (they doo it on o-bromo-phenol)
The NaHSO3 is an antioxidant.
And yes, when the sodiumsalt off hydroquinon is transferet to the DCE with help from the ammonium thing, the large excess off DCE make polimer formation unlikley.
The ethanol, afther the xtalisation is a bit brown, so I gues that some polimers is formed.
I will go on with the bromination.
And i'v seen that the aromatisation is posible with NBS (yes). You brominate the hydrofuran and then eliminate HBr in one step due to the energi won by the aromatisation.
 
   

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