02-15-02 18:06
No 270030
I'm no pharmacist, but i was wondering if anyone had ever heard of symmetrical amphetamines or phenethylamines, specificly the 4-isoproyplamino-2,5-meo-amphetamine substituted.
(Chief Bee)
02-15-02 19:38
No 270068
Are you talking about something that would look like this?
I'd believe that it would be inactive, as I don't know of any active psychedelics with two primary amino groups present. I have not seen the above made somewhere either, but I have seen 2,5-bis(ethylamino)-p-dimethoxybenzene, the phenethylamine analog, being made in a journal by the double addition of ethyl cyanoacetate to benzoquinone, followed by a few more steps.
(Stranger)
02-16-02 23:43
No 270584
why do you suppose that compounds with two primary amines present are inactive? Has anyone heard of any active symmetrical compounds?
(Chief Bee)
02-17-02 01:23
No 270627
All active psychedelics with a 4-substituent have one which is neutral or electronegative, because the serotonin receptor wants it to be that way for a good fit. Amines are (at least partly) positively charged at physiological pH, and thus not suitable as psychedelics. The 4-amino- and 4-acetamido- analogs of 2,5-dimethoxyamphetamine are inactive.
(Official Hive Translator)
02-17-02 20:33
No 270928
...... C_Nemo, a very respected & xperienced Russian bee , claimed to have made smth similar (bis-ethylamino-p-diMeO-benzene) by chloromethylation of p-diMeO-benzene followed by halogen/nitrile xchange and red'n.
There's no proof to the structure of what he made, but the properties of the comp'd he got were different, so he assumed it must've been bis-ethylamino thing (indeed seems to bee the only possibility). It was active though.
I can post the experimental details of his work if someone is interested.
Antoncho
(Chief Bee)
02-17-02 22:17
No 270972
That would be EXTREMELY interesting (together with bioassay too).
(Official Hive Translator)
03-01-02 17:50
No 275351
Please do not xpect much from this..... Jerry (that's his Russian pseudonym - a friend of Assholium's, BTW
) was very very sparse, as usual - those pro's, damn 'em!Anyway, here goes a verbatim transcryption of his notes:
1. In a 2-liter flask w/a gas absorption tube there are placed 64 g p-diMeO-benzene in 300 ml benzene and added ~30 g wet paraform (filtered from polymerized on standing formaline) and a stream of HCl is passed for 1,5 h. The precipitate is filtered through cottonwool. Filtrate is shaken twice w/cold water in a sepfunnel. Dried w/anh K2CO3 and evap off the benzene. The product crystallizes on standing (mp=69 C, lit. = 72 C). The obtained crude product is distilled in vacuo. Yield 16,3 g.
2. In a 150 ml flask there are dissolved 16 g of the above product in 60 ml acetone. Added 8 g KCN and 0,8 g NaI and refluxed for 24 h. The precip't't is filtered and washed w/acetone. After evap'n in vacuum there is left 7,2 g brown oil that crystallizes on standing.
3. For red'n of the bulk of the above crude product one takes 5 g LAH in 250 ml ether and treats as usual.
- see #20 (2C-B) in PiHKAL.
- 1 g of the product is obtained
- the product differs from the expected 4-bromo-2,5-diMeO-phenethylamine (!!)
- possibly, contains some 1,4-bis-(2-aminoethyl)-2,5-diMeO-benzene
I know that's not much - esp, details of bromination are missing. But i still think that's of significant value, since - while the yields are low, of course - that's the 1st known success w/chloromethylation of p-DMB - whatever the result might bee.
As you can see, Jerry wasn't particularly anal about purification of intermediates :) He's generally like that :)
Some additional info - the activity range, e.g. - can bee found in Post 15822 (C_Nemo: "Re: chloromethylation/formylationof 2,5-diMeO-somethin", Chemistry Discourse).
Antoncho
(Stranger)
03-03-02 21:42
No 276344
wow, so according to Post No 15822, there is a good possibility of increased activity there. the reason i brought this up was because i was wondering if activity (potency) would increase if there was a higher probibility of binding to receptors. thanks for the feedback.