2C-N

[dr_mabuse]

Hi there bees! This is my first post.  

After reading its PiHKaL entry, 2C-N triggered my attention. Dr. Shulgin describes similarities to MDMA but "it somehow comes up just a little short of expectations". Still he describes the material, despite having a greater body-load, as still being "okay".

There is nothing much to be found on the search engine either, except for what is mentioned in PiHKaL, and a recent post by Vitus Verdegast in General Discourse.

Inspired by Yellium's post

Post 439969

(yellium: ">I really can't figure out why this ...", Methods Discourse) I wanted to see if 2C-N also has that hidden potential that DON had, considering it's shadyness in the presence of the other more powerful 2C-X's.

And guess what: it sure holds potential!  


2,5-dimethoxynitrostyrene was prepared from the corresponding aldehyde, nitromethane and EDDA catalyst according to:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/edda.html

10 gr Nitrostyrene, recrystallised from EtOAc/EtOH as orange needles,  was submitted to the Zn/HCl reduction as described by Sunlight:

Post 406397

(Sunlight: "Test done", Novel Discourse)
I had a bad yield here, the cause of work up trouble, and this being the first time that I performed this reduction (as I always tend to fuck up the first time). I added the first portion of Zn over 2 hours instead of one, and after basifying and extracting with toluene I got a yelloworange organic phase.
I washed this repeatedly with water, performed an A/B with dil. sulfuric acid, basified this again and extracted with toluene. The yellow toluene layer was washed 2x with water, separated, dried over KOH, and gassed with dry HCl.

A dark coloured mess fell out of solution, which, after cleaning with ether and repeatedly with acetone, gave 1.2gr of an offwhite powder, 2,5-dimethoxyphenethylamine hydrochloride (2C-H).

2C-N
600mg of 2C-H.HCl were dissolved in 7 mL GAA, followed by dropwise addition of 2 mL 60% HNO₃. Cooling wasn't necessary for this small scale, as the mixture barely increased in temperature. Towards the end of the addition yellow solids separated, stirring was continued for 5 min after addition, 5 mL of dry ether was added and the mixture was filtered. The yellow solids were washed twice with dry ether and air dried, gave 500 mgs (63%) of a beautiful yellow powder.



The nitrate salt was used for all human titrations, as was done in PiHKaL

-

SWIMs results are similar but not quite the same of what it written by dr. Shulgin. He ingested the compound at 70mg, 100 mg and 120mg doses. There is a very rapid onset, effects are felt withing 30 min, like warm-and-cold sensations, pleasant body tingling and (armpit) sweating. SWIM was always giggly, good humoured and his mood was quite lifted. The body load is much bigger than the other 2C-Xs but not at all unpleasant or alarming. These are the MDMA similarities the doctor mentions. No increase in heartrate, no effects on breathing (except on 100mg my nose was suddenly cleared up), nothing.

What is different is that dr. Shulgin doesn't get any visual effects from it. For me, the compound has marked visual effects even at 70mg, and definately at 120mg, the colours and patterns reminded me of 2C-B.

Strange thing is that, at 70 & 100mg, the body load and visual effects were much more present than any psychological effects. No usual 'train of thoughts' running though my head, on contrary my thinking was suprisingly normal. Indeed a body +++ and mind ++.

But at 120mg SWIM did had profound effect on the mind which resulted in a marvelous +++ experience. The body load is always a bit heavier though.

The effects start to peak from 1 --> 2 hours, and start to wear off to be largely gone in 3 to 4 hours, depending on dose.

[Manichi]

You did good job dr_Mabuse!

As a matter of fact i am also interested in 2C-N, and i am about to synthetise some myself.  
Talk about coincidence!  

I must say that it is nice to meet you at hive, welcome!... as a matter of fact i am new too,
talk about coincidence!    

This look like a great forum this bee home, doesn´t it?

Liszt teach beauty.

[Vitus_Verdegast]

What a coincidence!    

Yep, SWIM actually tasted this material too in the last weeks and found it mighty interesting! Had a great time, the power of this substance should not be underestimated!

Also, considering the ease of its preparation, all is done within an hour starting from 2C-H.

Really nice, congratulations!

Notable thing is that 2C-N is apparantely a 5-HT₂ antagonist as opposed to the halogenated 2,5-dimethoxyphenethylamines and their DOx counterparts.

2C-N was a 5-HT2 receptor antagonist; the mechanism was competitive at the 5-HT2A, but non-competitive at the 5-HT2C receptor. The antagonism was time-dependent at the 5-HT2C receptor but independent of pre-incubation time at the 5-HT2A receptor subtype.

Post 457936 (missing)

(Vitus_Verdegast: "potency and efficacy of subst. PEAs at 5HT2A/2C", General Discourse)

[Bandil]

dr_mabuse>
You said it had quite a bodyload; could you elaborate a bit more on that? How stimulating was the compound compared to other 2C's? the propyl version(DON) seems to have a limit at 4-5 mg's where the stimulations get's to anoying to explore in higher dosages, so i was wondering how the ethyl version behaved with that property.

Regards
Bandil

[dr_mabuse]

Hi Bandil!   

The compound has a much greater body-load than 2C-B. My friend also agrees on this. I don't know if I would call it stimulating, I had the tendency to sit down all the time. Conversations were also a bit hard to concentrate on.

The first effects noticed are in fact physical euphoria, a tendency for stretching, a pleasant tingling of the skin, and a persistent sort of 'push' on the body, which lasts until the end of the experience.

That is why SWIM didn't dare to take a supplement, he was afraid that the push would become unconfortable in higher doses. Next time the plan is to take it to 150mg, but I suspect that the body load would become annoying too, as is also noted by dr. Shulgin.

DON looks very interesting too, I'd like to compare the effects between the two in the future.


PS Manichi: Yes, it sure is nice around here!  

[Chimimanie]

First let me say welcome to you both dr_Mabuse and Manichi.    I bet you will enjoy your stay at The Hive.  

Now that this is done, i can tell that I have found two patents listing 2C-N as an intermediate, here they are:

From

Patent US6171866

:

4-Nitro-2,5-dimethoxyphenethylamine:

45.5g (250 mmol) 2,5-dimethoxyphenethylamine was mixed with 40mL water and cooled to 0°C while 30 mL conc. HCl was added slowly. The resultant milky emulsion was cooled to 0 to 5°C, and 65 ml conc. HNO3 was added slowly and carefully within about 2 hours, keeping the temperature below 10°C. The mixture solidified when about half of the HNO3 had been added. 50 mL icy water was added to render the mixture stirrable. Then the rest of the HNO3 was added. The mixture was warmed up to room temperature and stirred at room temperature for 3 hours, was basified with 40% NaOH to pH > 12 and then extracted two times with CHCl3. The CHCl3 extraction was back washed three times with 0.5M NaOH and dried over K2CO3. The solvent was evaporated to afford 49.8g orange oil (yield: 88%), which crystallised when cooled.

And from

Patent US6525200

:

Synthesis of intermediate 33 (2,5-dimethoxy-4-Nitrophenethylamine):

To a 100mL Erlenmeyer flask equipped with a magnetic stirring bar were added 4.73g (26.1 mmol) of 2,5-dimethoxyphenethylamine and 4.2 mL water. The mixture was stirred and cooled to 0°C in an ice bath and 3.1 mL of conc. HCl was added slowly. To the resulting yellow solution 3.4 mL of conc. HNO3 was added dropwise at 0-5°C over a period of 1h. Then 12 mL of water was added to the solidified mixture and swirled to form a stirrable paste.Then another 3.4 mL of conc. HNO3 was added dropwise at 0-5°C over a period of 1h. The yellow mixture was refrigerated for 12h, then 20 mL of water was added and ultrasonicated to brake big chunks of solid. The suspension was cooled to 0°C in an ice bath and 10 mL of 40% NaOH was added slowly to achieve pH 12-13. The mixture was extracted with CHCl3 (3 x 10 mL) and the combined extract was washed with 0.5N NaOH (3 x 10mL), dried over K2CO3 (3g) and evaporated to dryness (15 mm) to give 5.4g (91%) of 2C-N as a brown oil which solidified after 0.5h at room temperature.

For microanalysis crude 2C-N was recrystallized from a 1:5 mixture of EtOAc/hexane and dried under vacuum (0.1 mm, RT) for 2 days; mp 64-66°C.

So the freebase is a solid   ... another interesting compound they made in this patent is the intermediate 37: 2,5-dimethoxy-4-dimethylaminophenethylamine. I wonder its activity.  

[Vitus_Verdegast]

Very interesting find, mr. Chimimanie!  

I have some doubts about the activity of 4-dimethylamino-2,5-dimethoxyphenethylamine, considering the inactivity of its 4-amino counterpart.

But hey, we will never know if no-one has tasted it yet.