DOC: Two attempts

tetraedr · Fri Mar 04, 2005 2:20 pm

I have got the Talking Asshole in my house. It follows me and whispers some shit things to my ear. Several days ago I heard very strange news about the synthesis of DOC using bubbling chlorine into GAA solution of 2,5-DMA-base. I just want to translate you some features of this story.
“One gram of DMA was dissolved in 10 mL of GAA, cooled down to 0C and chlorine gas was bubbled into this solution during 15-20 seconds. After that the flask was sealed with cork, stirred at 0C for 2-3 min, then these movements (bubbling and stirring) were repeated 2-3 times (until the chlorine stops react with solution). Bright yellow color appeared. Then this flask was kept for 20 min at r.t., poured into 80 ml of water, washed three times with DCM, (yellow color with mist was moved into organic layer). Obtained clear colorless water solution basified with KOH solution and extracted with ether. No product was there. Experiment was failed.”
Then Talking Asshole scratched his anal and continued.
“According PIHKAL #64, 0.76 g of 2,5-DMA was dissolved in 8 mL of GAA, cooled down to 0C and 0.5-1 mL of liquid chlorine was carefully added in one portion. The color becomes more dark-brown. This solution was kept at r. t. for one hour, poured into 60 mL of water, washed (3x30 mL) of ether, basified with KOH solution and resulting dark-grey solution was extracted (3x20 mL) of DCM. Combined organic layers washed with 20 mL of water, dried with sodium sulfate, concentrated under reduced pressure, obtained light-yellow oil dissolved in 5 mL of IPA, acidified with HCl (35%), concentrated under reduced pressure again, treated with ether and filtered off. Yield – 0.55g (53%) as a snow-white crystals with m.p. about 203C.”

Questions: Why the big difference in results for using gaseous or liquid chlorine? PIHKAL gives a different m.p.’s: 188C and 194C and 18% yield. Maybe, SWIM was wrong, and obtained substance is dichloro-derivative or something else?

sony · Tue Mar 08, 2005 4:00 pm

Yes it seems that shulgins method using chlorine is prone to give sidereactions and wont exclusiveley yield a monochlorinated product.

Perhaps sulfuryl chloride or NCS might be friendlier options for chlorinating.

tetraedr · Wed Mar 09, 2005 12:52 am

I am going to clear this situation by three ways.

1. I will run NMR-spectrum after several days.
2. I will try to use NCS (third attempt) later (NCS have been ordered)
3. I am going to find the volunteers to test this substance.

tetraedr · Mon Mar 14, 2005 7:04 pm

I have got the NMR today.

It is not a right compound - there are no CH-protons in aryl. I mean - it is a 2,5-dimethoxy-3,4,6-trichloramphetamine. What a pity!

But some people already tried this substance - it has psycho-activity, but so weak in 2 mg dosage.

tetraedr · Mon Mar 14, 2005 7:05 pm

I have got the NMR today.

It is not a right compound - there are no CH-protons in aryl. I mean - it is a 2,5-dimethoxy-3,4,6-trichloramphetamine. What a pity!

But some people already tried this substance - it has psycho-activity, but so weak in 2 mg dosage.

It is strange - I have found some info, that can be possible to made DOC using AcOH solution of chlorine. But my this attempt was also failed...

IndoleAmine · Dreamreader Deluxe

Maybe when you (read: your asshole) uses just a stoichiometric amount of chlorine? It would effectlively avoid overchlorination, but yield could be a bit on the low side... Laughing

Or with n-chlorosuccinimide or some other, more selective chlorinating agent? (edit: nevermind, I just saw that you had the same idea already)

i_a

tetraedr · Tue Mar 15, 2005 10:29 am

It is not a possible, to measure the right amount of liquid chlorine! It is evaporate so quickly!
Shulgin wrote, that he took the amount of chlorine using Pasteur pipette. It is not possible also - chlorine disappeared from pipette immediately.

So, will be only last attempt, with NCS. Watch our adertisement!

Guest · Tue Mar 15, 2005 11:53 pm

tetraedr · Mon Mar 21, 2005 7:05 pm

I have got the message from this substance (I decided to call it 3Cl-DOC) tester.

Dosage - 5 mg (he said, 10 mg should be better).

Increasing the action during 1,5 h.

Duration - about 6h.

This subsance very close to 2-CB, than to DOB. Light visuals, light euphoria. In conclusion, the Tester said, that he satysfied this substance and recommend it for next testers.

transistor child · gnome

It's probably just a small amount of monochlorinated product, hence the activity. Would really be interesting if you could post your results with NCS tho, when they're ready.

tetraedr · Tue Mar 22, 2005 9:51 am

IndoleAmine · Dreamreader Deluxe

You hear us Dr. Shulgin?

...one of us just found a new one..

(was it already on your to-do list maybe?) Very Happy

i_a

anime · Wed Apr 13, 2005 11:51 pm

Congrates tetraedr. you are a brave soul, I would have first fed it to my friends cat, glad to see that the product is active an non-toxic.

The NCS method should work, it is more selective to aryl halogenation, you could try Ammonium Chloride, H2O2 in GAA or NaCl and oxone to yield the DOC that you were originally looking at.

tetraedr · Thu Apr 14, 2005 12:32 am

I have not NCS in present, but somebody promised to bring it as soon as possible...

But one of the days I have got some little amount of NIS, and I think to make some experiment with it.

Does somebody here have the exact procedure for 2,5-DMA iodination witn NIS?

I mean to reflux it in chloroform. Is it right?

transistor child · gnome

Any follow up avaible?
Really interested in the halosuccinimides ability to halogenate amphetamines and phenethylamines. Did you ever tried it? According to a post on The Hive it should work on 2,4-dimethoxyphenethylamine in GAA with pretty good yields.