Author Topic: tBOC protecting group acceptable pharmacologically?  (Read 55 times)

Tsathoggua

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tBOC protecting group acceptable pharmacologically?
« on: July 25, 2010, 10:22:14 PM »
Title says it really, I had the idea for forming a novel prodrug of MDxx the other day, [edited - Enkidu], then forming the isocyanate followed by reaction with tert-BuOH to give a tBOC protected MDMA derivative, which as a formal amide should not be listed in the UK misuse of drugs act, and be therefore legal to posess, yet to open up into MDMA in stomach acid.

Two concerns :

1-will stomach acid prove concentrated enough to deprotect the amine.

2-is it possible for the hydrolysis to form a carbocation that goes on to alkylate the crap out of the next thing it meets with? under aqueous conditions, will it happen? tert-carbocations are the stablest of the lot so should at least be less reactive than a primary or secondary carbocation, but still one would wish I think, to avoid it, as one does with epoxides, quinones and the like as prooxidant nasties.


2-B-assuming it does form a carbocation from the  tBOC group, is it likely A-to first alkylate water forming tert-butanol (which is harmlessly metabolised into acetone and CO2) and B-what about likely forms of other metabolism, I.E possible metabolism to t-BuOH via amidases or esterases competing with any formed carbocation route to the same end product(s) ?

Viable thought?  what do you guys and gals think?
« Last Edit: July 26, 2010, 01:27:54 AM by Enkidu »
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Enkidu

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Re: tBOC protecting group acceptable pharmacologically?
« Reply #1 on: July 26, 2010, 01:30:29 AM »
Won't work, your end product would be a carbamate, which I don't think would be hydrolyzed. R-N-C(=O)-O-t-Bu

Trash, if nobody else has anything to say.

Tsathoggua

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Re: tBOC protecting group acceptable pharmacologically?
« Reply #2 on: July 26, 2010, 01:55:04 AM »
I'm not so sure, TFA is usually used, but wikipedia also references use of HCl.

I'm going to go bone up on the metabolism of carbamate muscle relaxants and nerve agents...should be abundant tox data on those insecticides and the likes of meprobamate, carisoprodol etc.
Nomen mihi Legio est, quia multi sumus

I'm hyperbolic, hypergolic, viral, chiral. So motherfucking twisted my laevo is on the right side.

jon

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Re: tBOC protecting group acceptable pharmacologically?
« Reply #3 on: July 27, 2010, 12:44:29 PM »
just n-benzylate it like they do with amphetamines.

Tsathoggua

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Re: tBOC protecting group acceptable pharmacologically?
« Reply #4 on: July 27, 2010, 03:31:41 PM »
The idea to avoid actually touching MDxx themselves, bypassing ever handling an illegal compound.
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I'm hyperbolic, hypergolic, viral, chiral. So motherfucking twisted my laevo is on the right side.

jon

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Re: tBOC protecting group acceptable pharmacologically?
« Reply #5 on: July 27, 2010, 04:43:50 PM »
tall order

Tsathoggua

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Re: tBOC protecting group acceptable pharmacologically?
« Reply #6 on: July 27, 2010, 05:14:02 PM »
The UK law is different from the US, its just as fascist, but bloody incompetent, having a drug in ones system doesn't count as posession in UK law, and unless a compound is either specifically named, or caught in one of several catch-all (read 'catch the odd few') clauses, it is legal.

Don't think there is anything covering wierd arsed carbamates like the potential MDxx variant, not something they would expect haha, hell, for a laugh, read the misuse of drugs act text some time, it reads like it was written by a dyslexic chimp on a solid dose of PCP, who happens to have prescisely zero grasp of chemical nomenclature.

around 1/4 to 13rd of the time, entries aren't even spelled correctly.

The filth still wouldn't like it one bit, but hey, I am not their biggest fan after all, after the repeated trumped up 'offences' that they have tried to invent against me, false charges and other such shite.
« Last Edit: July 27, 2010, 05:16:46 PM by Tsathoggua »
Nomen mihi Legio est, quia multi sumus

I'm hyperbolic, hypergolic, viral, chiral. So motherfucking twisted my laevo is on the right side.