(Official Hive Translator)
10-17-02 16:27
No 369598
      Zealot: synthesis and bioevaluation of PCDE
(Rated as: excellent)

As usual, a verbatim translation - of Post 368814 (zealot: " PCDE", Russian HyperLab) (synthesis) and Post 368917 (zealot: " PCDE.", Russian HyperLab) (bioassay), with my comments in italics.

The synthesis of PCDE

1. Cyclohexenyl-diethylamine and its tosylate salt.

Into a 250 ml flask equipped w/a Dean-Stark trap there's placed 68mls (65g) cyclohexanone, 71,5mls (50g) diethylamine and 1,5g tosyc acid monohydrate. The mixtr is refluxed until water separation ceases and the distillate's drops beecome completely clear. That takes ~5-6hrs.

129g tosic acid monohydrate (117g pure p-TSA) is added to 150mls toluene and boiled w/Dean-Stark until unhydrous. Thus obtained solution is slowly, w/good stirring and cooling admixed into the above amine soln.

Edit (added on 10 March 2004)

The instructions from the synth above apply only for the higher-boiling amines.

Zealot said he'd accidentally mixed the things up when doing the write-up (since the actual synth was performed a long time ago) - the described variation was used for making the morpholine analogue of PCP.

Diethylamine needs to bee gradually introduced thru a narrow pipette extending beelow the liquid's surface. Otherwise it'll boil away bee4 it forms the imine.
Furthermore, the rxn proceeds for 12-16 hrs.

This trick works even for the amines that are gaseous at RT, e.g., diMe-amine.

Then, another detail, it's best to use unhydrous tosic acid, which has been dehydrated by boiling in toluene.

<end edit>

2. Phenylmagnesium bromide.

Into a 500ml flask there's added 100mls ether, 12,9g Mg turnings and several iodine xtals. Stirring is commenced and a soln of 83g bromobenzene in 200mls ether is added as fast as possible, but not too fast lest the condenser chokes.

3. PCDE (N,N-diethyl-l-phenyl-cyclohexylamine).

Into the solution of 221g 1-cyclohexenyl-N,N-diethylammonium tosylate prepared in Step 1 (containing 104 g amine) in toluene there's added w/good stirring and cooling at 0 C the Grignar solution (145g) from Step 2. The addition is carried out as afast as possible. the mixtr is stirred for 0,5-1 hr, allowing the temp to rise gradually to RT.
The rxn is quenched by pouring into a 2 l beaker containing 300g ice, 100g NH4Cl and 100mls conc. aq. NH3. The organic layer is separated, washed w/water, dried w/MgSO4. The solvts are distilled off, ether at ambient pressure, toluene in aspirator vacuum.
Yield - 82,7g (57%)

To obtain the HCl salt the red oil is dissolved in ether and sat'd w/HCl.

The bioassay.

What i am about to tell you, my friends, has a very close relation to my recent thread on psychotechnologies. Initially i even wanted to post this report in there, but then a new topic on cyclidines appeared, and i posted this synth, and Antoncho asked for a report - all in all, the Fate itself demands me to share with you what i once have seen THERE.

I've made many cyclidines but this compound turned out to bee the most potent of them all, after PCP - and at the same time, the easiest to make. And by the fortunate accident, it happens to bee the only one of them all (xcept for ketaminic analogues) that i still use to this day. And - it is THE compound on which i have experienced two of the four most shocking/frightening/mysterious/grandieuse/enchanting/unexplainable trips in my life. Almost half a year has passed since the last time, but up to this moment the very thoughts in my head stall frozen as i begin to think of it.

I can't recall when it happened for the 1st time, but i remember very vividly how it all began. It started as a barely noticable ringing inside my ears that resembled of a sound of a chainsaw - in which a rhythm soon appeared. As if the noise was periodically fading and strengthening again. The frequency of the pulsations was pretty high. Then another sound added to the cacophony - a drumbeat. The noise beecame louder and louder.

I beegan to grasp for air and suddenly realized that the drumbeat was actually the sound of my loudly pounding heart! About 120 bpm (here i can't resist noting that a healthy person's heart can safely stand the heartrate that is calculated as follows: 220 bpm minus one's age; that is, ~190 bpm in this case. Of course, the main reason of concern in such cases is blood pressure, not heartrate). And then i was literally flooded by the wave of FEAR - not even fear, but an unexplainable HORROR. I was lying on my bed unable to move even my eyes. The wallpaper's pattern beecame very sharp and beegan flowing from the left to the right. Actually, the whole room was covered with blurred horizontal stripes. The colors began to fade as if someone was slowly turning down a TVset's color control. The darkness thickened. The chainsaw's howling beecame unbearable.

And then the room started to assume a different shape. Ordinary it is a prolonged rectangle, with two doors on the opposite sides - one to the balcony, the other leading to the corridor. But now the corridor door disappeared and there suddenly appeared another one, where there used to bee a wall. The door itself was black but its corners were lit as if with a luminiscent light. I was close to fainting. That bluish-white light was pulsing in unison with the rhythm of my insanely racing heart. I would have screamed but my body ceased to obey me. The only thought circulating through my head was: "What if i don't return now, never return". Don't know - maybee beecause of the overwhelming fear, or something else, but i suddenly beegan to feel my body again. And i crawled along my bed - that was a purely instinctive action. I didn't even think what i was doing and why - it was only later that i realized that i'd turned myself on the stomach and crawled - but that was the salvation. The light's pulsations disappeared, darkness went away, the wallpaper stopped flowing. Colors came back. Consciousness began to reinstall itself.

And some time after that i came upon a psychiatric site dedicated to the borderline states of consciousness and - you can imagine my feelings - discovered a description of a temporal epileptic seizure syndrome that was almost identical to what i'd experienced on PCDE! The only xception was that i didn't feel any weird smells like burnt rubber, sulfur etc. - and of course, no mention of any doors and such. But the whole picture - flickering lights, sharp unpleasant sounds, paralizing fear - all fit in very well.

Half a year ago i decided to undertake one more trip into that dimension. Only this time i was prepared for everything and could manage my fear. And came almost all the way till the very end. Why 'almost'? I'll tell you.

When the room was immersed completely in the darkness and its corners and the doors beecame lit with that unearthly light, the chainsaw's screaming started to gradually soften. I couldn't move again, but strangely could see almost 270 degrees around myself. Possibly, it'd been like that the previous time, only then i could see just some limited space and all the rest was enveloped in grey striped fog.

Light's pulsations gradually ceased. And the silence came. There was nothing else - just the darkness and the horrible shining around the doors and the room's corners. And then i realized that the silence was absolute, even my heart wasn't beating! I lay on the bed, enchanted by this silence. It wasn't a 'ringing' silence - it was the ABSOLUTE silence.

And then thoughts started coming inside my head out of the air, of nowhere. I understood that where i was it was the 'space in between'. I stared at these doors and was frightened to approach any of them. I didn't know what was beehind them. But i realized very clearly my insignificance and smallness. Alone in this horrendous room. Alone - face to face with who-knows-what. I suddenly understood that the universe doesn't give a shit for any of us. That there exist worlds in it which are totally alien to the human world. Frightening in their incomprehensibility and their unintelligible laws. And what if i step into one of these worlds. And meet there something that will destroy me faster then i beecome conscious of myself. Something DIFFERENT. Not beecause it is evil, but simply beecause it won't even suspect any consciousness in me and smash me on the floor just like we smash cockroaches in our kitchens. We don't ever think cockroaches are capable of loving or writing poetry, do we? Funny, isn't it?  We here in this world of ours are so fond of 'Love', cherish it, make a cult of it, sing the beaty and power of human mind - but someone else will not even suspect a sparkle of consciousness in us. Will run us over and won't notice it.

And so i was there, lost in contemplating the meaninglessness of our lives, all the goals that seemed important and noble bee4 turned out to bee a fiction, imposed on us by social stereotypes and something else - i don't know what and whom. And in THERE i understood Ecclesiast's words: "...human life and animal life is one, and the breath for the both is one, and there is no advantage for a man to a cattle, for all is meaningless". It was horrible to realize this ABSOLUTE MEANINGLESSNESS OF LIFE. Horrible to realize the absolute freedom and unshelteredness. i never thought that freedom can bee so frightening and unwanted.

I didn't enter any of the doors.

And upon passage of some time i bought a CD w/an underground techo music - usually i never buy techno, always 'dance' or 'techno-dance', but this time decided to take a look. And in one of the tracks i recognized that unmistakable howling of the chainsaw. The composition's name is 'Die Offenbarung.mp3' by Johannes Heil.(this composition, found in the web by Hellowin of HyperLab, can bee downloaded at (10,6 Mb)). If someone happens to find this record, he'll know approximately what i heard then. Since that time i call such music 'the music of temporal epileptics'. I often wonder what made Johanness Heil create this rhythm and instrumentals.

Hope you find this interesting, bees,

(Hive Bee)
10-17-02 16:59
No 369603

Double wow!..Thats all I can say.

Brains and balls wink

Catalytic hydrogenation freak
(PVC-Analog Taste-Tester)
04-27-03 19:03
No 429774
      Thanks for the trip report!     

Thanks for the trip report! I've done a lot of phencyclidine analogues, and ripped my mind apart several times over, but that sounds unique.. Sounds like a good time!smile Yes, tosic acid = p-toluenesulfonic acid. The Schiff base has to be converted to a tosylate or some other type of similar salt, or else you'll get no yield. It's another story when using lithium instead of Mg. Peace!cool

Love my country, fear my government.
(Hive Bee)
03-10-04 14:18
No 494184
      High! First thanks for the report....     


First thanks for the report.... PCDE is a Compound swim is interested in for a long thime :)

But now as he tries to do the synthesis problmes come up at the first step:

In your procedure you dont use any solvent like Toluene - SWIM accidently overread this and added Toluene - result:

As Diethylamine boild at a lower temperature as the Toluene/Water-Azeotrope the water seperation doesnt workt and only diethylamin distills into the dean stark receiver...

Now a second trial is running without any solvent - but: Diethylamine is miscible with water, so how could there ever be some water seperation?

I think using benzene might be the only solution.... any ideas/comments? crazy

best wishes,
(The Archetypical "Good Guy")
03-10-04 14:30
No 494186

I can see where your "complaints" about the solvent issues are coming from smile...

How about using molecular sieves for the reaction? It's on 3/4 mole scale. So if we just say that it will separate about a mole of water, it's well above what is actually needed. The water containing capability of 3A mol. sieves is 21%, so you'd need about 85 g's of the little suckers for the reaction given above...

Nuke the whales!
(Hive Bee)
03-10-04 14:46
No 494191
      High bandil! thanks for the quick response....     

High bandil!

thanks for the quick response.... Swim has some Molecular sieves available, but i think the following might be a problem:

Molecular sieves dont absorb water good enough when hot....
But the reaction might be too slow when the mixture is cold...

What do you think?

Should i just add the sieves to the toluene solution and stir for some time (days ?)

best wishes,
(Official Hive Translator)
03-10-04 15:02
No 494196

The instructions from the synth above apply only for the higher-boiling amines.

Zealot said he'd accidentally mixed the things up when doing the write-up (since the actual synth was performed a long time ago) - the described variation was used for making the morpholine analogue of PCP.

Diethylamine needs to bee gradually introduced thru a narrow pipette extending to the bottom of the flask. Otherwise it'll boil away bee4 it forms the imine.

This trick, according to Zealot, works even for the amines that are gaseous at RT.


P.S. This, along with some other comments from Post 437560 (zealot: "", Russian HyperLab), has been edited into the starting post of the thread.
(The Archetypical "Good Guy")
03-10-04 15:05
No 494198

Yes i suppose if you actually want to reflux the solventless reaction, it would require quite high temperatures. But the reason in this case for using reflux is to remove the water (as i see it). I don't know anything about the reaction kinetics in this case, but if it follows that of an imine formation, for instance, it shouldn't require that drastic reaction temperatures. Maybe it's even sped up by the presence of the molecular sieves?

Perhaps you could try it out on microscale at 50oC, 100o, 150oand follow the progress with TLC? It sure would be an interesting experiment smile


Nuke the whales!
(Hive Bee)
03-10-04 15:34
No 494206
      High! @Antacho: It would be rather important...     


@Antacho: It would be rather important if changed reaction conditions, etc that come up after the original writeup would also be translated and transferred into the english threads...

SWIM has now put everything together and added 4A molecular sieves... swim will stir the mixture for a few days and then distill....

Do you think it may be possible to get to the enamine via this way? Since the reaction is a equilibrium-reaction the water that gets absorbed by the sieves should cause the formation of more enamine...

thanks for the help, bees!

03-10-04 15:52
No 494207
      A few days sounds a bit too long :-) Shaking...     

A few days sounds a bit too long smile Shaking over night or 24 h might be enough. Avoid fast stirring if you don't want to sand your glassware. You can even do an azeotropic distillation after that to remove the last traces of water and of the amine.
(Hive Bee)
03-10-04 16:17
No 494211
      thanks lilienthal...!     

thanks lilienthal...! cool

 ill try to follow the reaction via hplc - that gives my ghetto HPLC-system a very useful purpose now :) the first practice-test blush
03-10-04 17:27
No 494217
      You have to take measures against imine ...     

You have to take measures against imine degradation during analysis, i.e. absolutely water and alcohol free conditions and/or strongly basic conditions. TLC is probably way better suited for this special task...
(Hive Bee)
03-23-04 17:56
No 496855
      High! I have to report that using molecular...     


I have to report that using molecular sieves in enamine-syntheis doesnt work to well!

Cyclohexanone (0,4mol), Diethylamine (0,4mol), 100ml Toluene and 500mg p-Toluene Sulfonic acid were combined in a 500ml Flask, and 50g of molecular sieves 4A were added. The mixture was slowly stirred for 4 days. (color change from a slight yellow to a darker yellow)

Afterwards the sieves were filtered off, and washed with some additional toluene. The excess diethylamine was evaporated at 760mmHg, and the toluene was removed on the rotovap under reduced pressure. The ressidue was distilled at aspirator vacuum to get a lot of unreacted cyclohexanone, and 16,2g of the enamine (bp.: 85C @ 14mBar) - a molar yield of 25% crazy

A better method would be to use a dean stark receiver and inject the Diethylamine slowly with a syringe into the boiling mixture, as suggested by antoncho!

The enamine was used in the synthesis of TCDE the day afterwards (enamine was sitting in freezer and changed colour from colourless to yellow within this 24 hours!), but no product could be recovered from this synthesis... i dont know if the (composed ?) enamine is the thing to blame for this...

ill hope the info is usefull anyway laugh

best wishes!
04-15-04 00:26
No 500855
      isopropylamine analogs of PCP     

is there a reason why there is no information on PCIp type drugs.  It seems like a logical choice, but I have been unable to find information on them.  Perhaps they are typically inactive?
05-18-04 04:30
No 507833
      nice i searched a long time before to find...     


i searched a long time before to find things on the imine pcp analogs synthesis.

i always wanted to know why use of PhLi whereas PhMgBr
now i know becose with PhMgBr you need the tosylate!
05-22-04 22:49
No 508840
      (1Gram Mg + H2SO4 ---> 3Grams MgSO4) MgSO4...     

(1Gram Mg + H2SO4  ---> 3Grams MgSO4)
MgSO4 works very well for imines synthesis.

1st: 1Gr MgSO4 (finely powdered, and microwaved), and 1Gr of the amine + the ketone are mixed, stirred in a closed test tube (stirred 4x10 min in 24h), then mixt is nearly not liquid, so toluene (5mL) is added, stirring again, and you get the imine (the MgSO4 completely separates when adding the toluene).

yield = more than 95% (you nearly dont smell the amine anymore)

Maybe it works only with imines! enamines: i completely dont know.

if you use too big amount of MgSO4, after adding toluene you'll still get some separated imine, but a big part of the imine will stay with the MgSo4, so use much toluene, or use mininum MgSO4 (start with 1gram MgSO4 for 2-3mL amine and then add more if needed).

anyway: if it smells the amine, add more MgSo4.
it must mainly smell the imine.
(Hive Bee)
07-20-04 19:46
No 520441
      temporal lobe epileptics brains have displayed     

temporal lobe epileptics brains have displayed similarities to that of meditating monks brains and preying nuns brains while they recall mystical/mediitative experiences.   some scientists have begun referring to this site of neural activation as the "god" part of the brain and this certainly makes sense when i consider the experiences i've had on NMDA antagonists.

not sure if this concerned you but i wouldn't bee to concerned about the common features the subjective experience has with TLE seizures.

just an interesting bit of second hand speculation,   there's supposed to be evidence that many famous religious figures suffered symptoms of TLE siezures!!!   i wouldn't be surprised if this is how modern christianity/catholicism got strarted