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Author Topic: Drugs that can be made from paracetamol(and other OTC drugs)  (Read 418 times)

Naphyrone

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Drugs that can be made from paracetamol(and other OTC drugs)
« on: February 18, 2011, 08:26:07 AM »
So lately i've been trying to think of decent drugs that can be made from paracetamol as a starting material and thought that this subject could use it's own topic for others to contribute. The easier to make, less steps, less non-otc reagents the better however I'm curious to see what some brainstorming can do.

The first one I came up with is a benzodiazepine.
7-methoxy-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one



You would start with the paracetamol, methylation with halomethane then deesterify the amide.
The rest is the rhodium benzoylchloride and chloroacetyl chloride procedure.

The next is N-[2-(dimethylamino)ethyl]-N-(4-hydroxyphenyl)acetamide which im guessing would be a weak opioid.



However i'm thinking if you have the chloroacetyl chloride from the first reaction you could make an amide with phenethylamine then react with the paracetamol but the problem is with the reduction of the ketone, do it before maybe? then carry out a methylation of the secondary amine and hydroxy group to decrease polar surface area.
That's all i've come up with for now.
« Last Edit: February 18, 2011, 10:44:33 AM by Naphyrone »

pyramid

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Re: Drugs that can be made from paracetamol(and other OTC drugs)
« Reply #1 on: February 18, 2011, 04:57:48 PM »
"The easier to make, less steps, less non-otc reagents"
Haha
Well benzoyl chloride, chloroacetyl chloride...not too otc at all, and if they are to be otc it will take a lot of work.
Hwever you can make benzoquinone and Hydroquinone from paracetamol. This chemical just is not a very good precursor in my opinion though

akcom

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Re: Drugs that can be made from paracetamol(and other OTC drugs)
« Reply #2 on: February 18, 2011, 07:01:54 PM »
Everyone wants a drug they can make from paint thinner and draino.  If that's your bag then start crushing up some PSE pills and get to work.

Interesting idea Naphyrone.  Is that benzo known to be active?

Naphyrone

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Re: Drugs that can be made from paracetamol(and other OTC drugs)
« Reply #3 on: February 18, 2011, 08:17:37 PM »
Akcom, I don't see why not, it's diazepam with the 7-chloro subbed for a methoxy. Any analogs of drugs that are schedule 3 can't be prosecuted by the dea however, the fda can still get you for selling an unapproved drug for human consumption.

guyp

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Re: Drugs that can be made from paracetamol(and other OTC drugs)
« Reply #4 on: February 18, 2011, 09:41:08 PM »
Quote from: Naphyrone on February 18, 2011, 08:17:37 PM
Akcom, I don't see why not, it's diazepam with the 7-chloro subbed for a methoxy. Any analogs of drugs that are schedule 3 can't be prosecuted by the dea however, the fda can still get you for selling an unapproved drug for human consumption.

Continue your research, with paracetamol being inexpensive I see no reason why you shouldn't. It probably will not come to fruition but it will certainly be a fun side project and you will learn much from it.

The Chloroacetyl Chloride (refs on Google) can be subbed and you should look into a substitute for the Rhodium Benzoyl Chloride. Would Sodium Benzoyl Chloride be a suitable replacement?

Most are just looking for quick and easy reagents from the aisle and ignore that there are many things unwatched that can be acquired with proper planning and a little imagination.

As I heard once some time ago:

"If it ain't Fake and Shake and it ain't from Wally World then they ain't having it".

2bfrank

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Re: Drugs that can be made from paracetamol(and other OTC drugs)
« Reply #5 on: February 18, 2011, 09:57:01 PM »
I haven't checked the chemistry here, to see for myself if its sound, as I'm just buzzin through here real fucking fast, but that said, its nice to know you can, but is such a benzo derivative worth such a fucken effort. For me it aint, and as for selling shit, man, hahaha, yeah they'd like to paint that little picture, but we all know that shit aint what were about. So listen up motherfuckers.

micro

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Re: Drugs that can be made from paracetamol(and other OTC drugs)
« Reply #6 on: February 18, 2011, 10:14:18 PM »
Well the obvious 2C-x and DOx series come to mind.
I'm not terribly good at novel compounds.

jon

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Re: Drugs that can be made from paracetamol(and other OTC drugs)
« Reply #7 on: February 19, 2011, 02:54:13 AM »
benzodiazepienes are'nt worth the bother they are uninteresting drugs.
you can just but the appropriately substituted 2-amino benzophenones from china.
chloro acetyl chloride is acetic anhydride and chlorine gas the rest is a cakewalk.
if you want to get on something interesting from something available try tweaking around codeine.
the 14-methyl codiene is ridiculously potent 10,000 times that of morphine.
14-cinnamoyl codeinone is 118 times stronger than morphine here are a couple of good books.
also look at bird repellant it contains methylanthrilanilate.
« Last Edit: February 19, 2011, 02:56:50 AM by jon »

Happyman

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Re: Drugs that can be made from paracetamol(and other OTC drugs)
« Reply #8 on: February 19, 2011, 04:17:06 AM »
4-Methoxy PCP seems like the best idea, any idea on going about it?

My suggestion would be para-Methoxyphenylpiperazine. I don't know how you would approach it though. Do you think (2-chloroethyl)amine would cleave off the acetyladehyde? Well I drew a pretty picture, but it would be best to turn the hydroxy group into a methoxy group first.

« Last Edit: February 19, 2011, 04:19:08 AM by Happyman »

jon

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Re: Drugs that can be made from paracetamol(and other OTC drugs)
« Reply #9 on: February 19, 2011, 06:17:18 AM »
nitrogen mustards!!!

Methansaeuretierchen

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Re: Drugs that can be made from paracetamol(and other OTC drugs)
« Reply #10 on: February 19, 2011, 11:14:13 AM »
Quote from: Happyman on February 19, 2011, 04:17:06 AM
4-Methoxy PCP seems like the best idea, any idea on going about it?

My suggestion would be para-Methoxyphenylpiperazine. I don't know how you would approach it though. Do you think (2-chloroethyl)amine would cleave off the acetyladehyde? Well I drew a pretty picture, but it would be best to turn the hydroxy group into a methoxy group first.


Methylation of paracetamol should be easy. Make the sodium- or better potassium salt and react with methylating agent (DMS or TMP) in acetone or DMF. Destroy methylating agent with aq. NH3. Make acidic and extract with ethyl acetate etc.. Evaporate organic layer.

Saponify N-Acetyl-group with KOH in butanol under reflux for some hours. Evaporate butanol, add water an extract with toluene etc.. Destill the p-Methoxyaniline.

But working with (2-chloroethyl)amine seems to be a bad idea... sounds like a mild blister agent but yes it works...
Quote
1-(2,5-Dimethoxyphenyl)-piperazine Dihydrochloride

A mixture of bis(2-chloroethyl)amine hydrochloride (23.3g, 131 mmol), anhydrous K2CO3 (18g), freshly distilled 2,5-dimethoxyaniline (20.0g, 131 mmol) and diglyme (75 mL) was heated at reflux for 48 h, allowed to cool to room temperature, and then poured into water (200 mL). The aqueous mixture was made basic (about pH 12) by the addition of a saturated KOH solution and was extracted with ethyl acetate (3x200mL). The combined organic portions was washed with water (3x200mL), dried over MgSO4 and evaporated to dryness under reduced pressure to yield a dark oil.

Vacuum distillation afforded 18 grams (62%) of the amine as a light-yellow liquid, bp 142-146°C at 0.18 mmHg. A saturated soln of HCl gas in anhydrous diethyl ether was added to a solution of the freebase in a small amount of 100% ethanol (can use methanol) to give the title compound, mp 218-220°C after recrystallization from 100% ethanol.
Reference: J. Med. Chem. 29, 630 (1986)

http://en.wikipedia.org/wiki/Vesicant
http://en.wikipedia.org/wiki/Nitrogen_mustard
« Last Edit: February 19, 2011, 11:36:44 AM by Methansaeuretierchen »

Evilblaze

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Re: Drugs that can be made from paracetamol(and other OTC drugs)
« Reply #11 on: February 19, 2011, 07:45:49 PM »
Working with di(2chloroethyl)amine is not so bad at all, just be careful and don't drink it, but 4-hydroxy-BZP doesn't seems like something active, but if it is, than I can make a report from how to make it (4-nitrophenol is available) so I can easily make 4 hydroxy and 4 methoxy-BZP also.

Is there any BZP analouge that won't cause headaches, nausea? And it is active in lower dose like 1-20mg? If yes and it is not simply BZP (what is illegal at us) than I could make a report from it's synthesis.

atara

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Re: Drugs that can be made from paracetamol(and other OTC drugs)
« Reply #12 on: April 02, 2011, 05:48:36 AM »
Indapex, anyone? I'm in a pictoral mood. Starting from O-methylparacetamol:

http://its.goofyti.me/u/http://i.imgur.com/CH70G.png

The first step is a FC-acylation, the second is a Wolff-Kishner, and the third is a Madelung indole synthesis. Eschweiler-Clarke methylation gives indapex (cyclisation is a nonissue; 2-position is already substituted).
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