Author Topic: Midodrine: a 3-step way to 2C-B  (Read 737 times)

0 Members and 1 Guest are viewing this topic.

Antoncho

  • Guest
Midodrine: a 3-step way to 2C-B
« on: February 28, 2002, 09:16:00 AM »
There's a prescription anti-hypotensive prescription drug called Midodrine, aka ProAmatine. It is available as either tablets or 1% solution. And it is a three-step and very OTC precursor to either 2C-X's or BOX'es.


2-amino-N-(b-hydroxy-2,5-dimethoxyphenethyl)acetamide

Wow ;D

Anyone wants to comment or suggest smth on this? ;)

Antoncho

hest

  • Guest
Re: Midodrine: a 3-step way to 2C-B
« Reply #1 on: February 28, 2002, 09:34:00 AM »
I guess the body will hydrolyse the amide to the amine. Most of the alpha-hydroxy compounds is active so you just need to brominate it :-)
The prescripton agains to high blodpresure is 30mg/day that shuld bee enough :)

Osmium

  • Guest
Re: Midodrine: a 3-step way to 2C-B
« Reply #2 on: February 28, 2002, 02:26:00 PM »
Let's make this a one pot synth. Iodinate the 4 position, throw in some rP and additional I2, reflux the shit out of it and you might end up with 2C-I...  8)

Is this a brain fart? Didn't have much sleep last night, I'm not really awake today, so excuse me if that didn't make much sense.  ::)

I'm not fat just horizontally disproportionate.

Osmium

  • Guest
Re: Midodrine: a 3-step way to 2C-B
« Reply #3 on: February 28, 2002, 02:28:00 PM »
Shit doesn't work, the HI will eat the methoxies. Oh well. It sounded good for a second or two.

I'm not fat just horizontally disproportionate.

PolytheneSam

  • Guest
Re: Midodrine: a 3-step way to 2C-B
« Reply #4 on: March 01, 2002, 12:23:00 AM »
You could put the methoxy groups back on after the rp/I2 reaction.

Where can I get some red phosphorus?

http://www.geocities.com/dritte123/PSPF.html

Rhodium

  • Guest
Re: Midodrine: a 3-step way to 2C-B
« Reply #5 on: March 01, 2002, 02:00:00 AM »
How about the drug Methoxamine as a DOB precursor?


Antoncho

  • Guest
Re: Midodrine: a 3-step way to 2C-B
« Reply #6 on: March 01, 2002, 08:18:00 AM »
..... yep, both P/I2 and P/HI will ruin the methoxies.... :(  :(  didn't think of it bee4.

Putting them back would also bee problematic beecause of NH2 methylation. Of course, there's an amide protective group in midodrine (but not Methoxamine), but reduction of  the OH will cleave it as well :(

Birch is an option, obviously - but it is much harder to do.

The best one could w/these things is probably to make them into BOX compounds - they also seem to bee quite worthwhile, as well as unexplored.

What i don't know is - how does one methylate aliphatic hydroxies? I know they're much harder to methylate - DMS doesn't do that, ordinarily.

If there was an easiysh way - then after the methylation/halogenation one would have an active comp'd! (In case Lugh's most valuable suggestion about amides being cleaved by the body works out)

So, dear chemical gurus, can you help? ;)

Antoncho

Lilienthal

  • Guest
Re: Midodrine: a 3-step way to 2C-B
« Reply #7 on: March 01, 2002, 04:16:00 PM »
Just hydrogenate it off...

PolytheneSam

  • Guest
Re: Midodrine: a 3-step way to 2C-B
« Reply #8 on: March 04, 2002, 12:51:00 AM »
While looking through the Journal of Medicinal Chemistry I found in Vol. 13, No. 5 (1970) page 1022 the article "Derivatives of 2,5-dimethoxy-4-methylamphetamine (DOM)" which gives syntheses for DOM with an OH group on the carbon connected to the benzene ring and the phenethylamine (not amphetamine) homolog (analog?).  The second sentence of the article says:


These two compounds might possess hallucinogenic and/or sympathomimetic properties.




There's three foot notes with references.  I wonder if you could take 2,5-dimethoxyphenylpropanolamine (Methoxamine) and brominate it to get something like DOB in effects.


http://www.geocities.com/dritte123/PSPF.html

Antoncho

  • Guest
Re: Midodrine: a 3-step way to 2C-B
« Reply #9 on: March 04, 2002, 08:19:00 AM »
...... interesting, but in PiHKAL #16 BOHD; 2,5-DIMETHOXY-beta-HYDROXY-4-METHYLPHENETHYLAMINE is described as inactive and spectacularly hypotensive at 50 mg.

Antoncho