Question Protected Amines?

[CryoThio]

This article got my attention and curiosity.

Identification and characterization of N-tert-butoxycarbonyl-MDMA: a new MDMA precursor - PubMed

In September 2015, 80 litres of a viscous, light-red liquid, described as hair product, was seized by the Australian Border Force (ABF). Initial testing by ABF indicated that the liquid was the 3,4-methylenedioxymethamphetamine (MDMA) precursor chemical safrole and custody of the material was...

pubmed.ncbi.nlm.nih.gov

Apparently, in 2015, authorities seized tert butoxy Carbonyl mdma, which is just mdma with protecting group stuck on the amine.

I think this might be a great way forward toward drug smuggling, and consumption in general. It was found that this t boc mdma was a prodrug for mdma when ingested. So one can consume illicit substances legally.

I doubt this would fly in the US, and doesn't fly in Australia, legally speaking, but many other countries could possibly benefit from this.

Question is, why is this not more common and known? I'm guessing because one has to use the illegal drug to make the legal drug, basically.q

 

[KokosDreams]

It's indeed interesting to think about. Similar things are done with cocaine smuggling currently, liquifying cocaine and mixing it with other substances like ceramic or concrete.
When groups use techniques like this I would assume each group has their own ways which they try to keep as hidden as possible.

In most cases it will make more sense to build a lab and produce the drugs 'on sight' instead of moving bulk around the world, punishment for precursors is not that high as for drugs, depending on the case.

 

[CryoThio]

Absolutely, the ”standard” ways of drug distribution are the standard for a reason.

The only way this would make sense is if someone was trying to sell them in countries with analogue laws, or trying to have a shred of legal hope for say transporting person use amounts across borders.

 

[CryoThio]

the Only way it Would make sense is if one could attach the amine group AND the protection group at the same time, technically avoiding making the illegal drug at any point. But that seems unlikely.

 

[Osmosis Vanderwaal]

You'd be surprised what some prodrugs are. This was a low effort campaign, there are metabolic processes that are nearly impossible to recreate chemically, that turn benign chemicals into drugs. Your liver is a master chemist that can, for instance, turn horse dewormer (levamisole ) into aminorex, a strong stimulant.. there are prodrugs to lsd meth and many others that have to be msgc to know because they don't test positive for drugs

 

[CryoThio]

Would you be so kind as to dm me about some of said drugs? Thank you

 

[Osmosis Vanderwaal]

Generally speaking, by the time illicit prodrugs are named, they are illegal. This patent at the bottom has many routes to prodrugs of illicit substances, this link talks about a lot without laying out the chemical names https://www.mdpi.com/1420-3049/13/3/519
Here's some other info;
1p-lsd
GBL 1-4 butanedione
N,t-boc-mdma
"A variety of prodrugs of amphetamine and/or methamphetamine exist, and include amfecloral, amphetaminil, benzphetamine, clobenzorex, D-deprenyl, dimethylamphetamine, ethylamphetamine, fencamine, fenethylline, fenproporex, furfenorex, lisdexamfetamine, mefenorex, prenylamine, and selegiline

1-Aryl-3-phenethylamino-1-propanone hydrochlorides 1-10, which are potentialpotent cytotoxic agents, were synthesized via Mannich reactions using paraformaldehyde,phenethylamine hydrochloride as the amine component and acetophenone, 4’-methyl-, 4’-methoxy-, 4’-chloro-, 4’-fluoro-, 4’-bromo-, 2’,4’-dichloro-, 4’-nitro-, 4’-hydroxyacetophenone or 2-acetylthiophene as the ketone component.

N,N-dipropargyl-2-phenylethylamine and N-propargyl-2-phenylethylamine

US20080318905A1 - Prodrugs and methods of making and using the same - Google Patents

Prodrugs of parent drugs and methods of making and using the same are described. The prodrugs comprise an amine-containing parent drug moiety and a prodrug moiety, such as methoxyphosphonic acid or ethoxyphosphonic acid. The prodrugs may be employed in therapy for the treatment of various...

patents.google.com

 

[HerrHaber]

Note that it should be taken care whenever the word “cytotoxic” appears in the same group of sentences. The meaning is vague from antibacterial to hardcore chemotherapy and why not refer to 4-chloroamphetamine that exterminates serotonergic neurons (it is argued to give the most euphoria but clearly it would be the last time getting high). The point is in documenting very well the known data about all compounds to see if it does worth obtaining them before you do. You may be a great synthetic organic chemist but don’t let biochemistry kill you.

 

[Osmosis Vanderwaal]

I'm not a chemist at all. Not even close. I just wanted to respond to his request with some information that was relevant. L-dopa and aspirin are prodrugs but not that interesting. People ask me about chemistry way more than they should, and off I go hunting for references, which I am really good at. CHEMISTRY, I have thought about for maybe 2 years.

 

[HerrHaber]

Getting the right references is pretty much chemist in my eyes. You also need to speak the language in order to extract the relevant informations and before interpreting them, just sprinkle some sense of chemistry for your interpretation to make sense until it does. Getting the right references for chemistry containing topic is uncommonly the first trait but it can be used to unlock the door to the sacred corridor where some doors will still be locked at least for some while, but most will be open and quite a few will be other corridors. Getting lost needs to be assumed before worrying about it and the light you gathered will shine your path. Allow me to disagree with that “not even close” of yours without boosting your self esteem more than needed for me to regret, and the right way is promised from me. For as far as I have the knowledge to help, the good referencing is apart for the brick by brick nature of efficiency in teaching yourself chemistry or to others (where I deem it mandatory). A chemist is also good in spotting the notions you need to assimilate starting from the basics, the experimentalist is rather hard to describe and a complex character but the way I see it: “as long as you make honey you are a bee”. I just surprised the biologist I am to say a big mistake, but the insect corridor of mine is in my entomology gallery in the invertebrate department I hate getting lost into. Cheers
P.S. the above text is for all readers and I hope everyone gets to where he wants. I expect, say “German quality chemistry” just from the one almost there.

 

[HerrHaber]

tBOC and FMOC are well known amino protecting groups but also acyls will normally do if harsher conditions are involved (greater losses depending on acyl). You may also peek on their enzymatic hydrolysis which may be cool due to reusability and specificity if deprotection should be performed (1pLSD is also a prodrug but needs not to be deprotected, this will happen after ingestion).