ATC code N06AA PubChem CID 436156 Molar mass 155.261 g/mol | CAS Number 801156-47-8 ChemSpider 385727 | |
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Legal status DE: Anlage I (Controlled)
UK: Temporary Class
Illegal in China, Finland, Florida Synonyms MPA; Methiopropamine; Methedrene; Syndrax | ||
Methiopropamine (MPA) is a thiophene ring-based structural analog of methamphetamine originally reported in 1942. Chemically it is not a phenethylamine or amphetamine and is not their functional analog either. It originally appeared for public sale in the UK in December 2010 as a "research chemical" or "legal high", recently branded as Blow. It has limited popularity as a recreational stimulant.
Contents
Pharmacology
Methiopropamine functions as a selective norepinephrine-dopamine reuptake inhibitor that is approximately 1.85 times more selective for norepinephrine than dopamine. It is approximately one third as potent as dextroamphetamine as a norepinephrine reuptake inhibitor and one fifth as much as a dopamine reuptake inhibitor. It displays negligible activity as a serotonin reuptake inhibitor.
Metabolism
For N-alkyl amphetamines, deamination and N-dealkylation are the major elimination pathways and renal excretion is a minor one. Methiopropamine is metabolized into active thiopropamine, 4-hydroxymethiopropamine and thiophene S-oxides. These N-demethylated metabolites are further deaminated by the cytochrome P450 enzyme CYP2C19 in the liver transforming them into inactive 1-(thiophen-2-yl)-2-propan-2-one which can be seen as a phenylacetone derivative.
Thiophene-2-carboxylic acid is the final major metabolic product. It is very hydrophilic and is excreted in urine. Methiopropamine and especially thiopropamine are also excreted renally, unchanged.
Synthesis
There is a four-step synthesis of methiopropamine. It begins with (thiophen-2-yl)magnesium bromide, which is reacted with propylene oxide, yielding 1-(thiophen-2-yl)-2-hydroxypropane which is reacted with phosphorus tribromide, yielding 1-(thiophen-2-yl)-2-bromopropane which is finally reacted with methylamine, yielding 1-(thiophen-2-yl)-2-methylaminopropane.
China
As of October 2015 MPA is a controlled substance in China.
Finland
Methiopropamine is illegal in Finland.
Germany
Methiopropamine is explicitly illegal in Germany.
United Kingdom
Following the ban on ethylphenidate authorities noticed an increase in methiopropamine use by injecting users. The ACMD suggested it be banned on 18 November 2015 as it had similar effects to ethylphenidate. The government enacted a temporary drug control order a week later which came into force on 27 November 2015. Though ordinarily the TCDO would only last 1 year, the ACMD reported that since its invocation prevalence of MPA had significantly decreased, and that it had been challenging to collect information about the drug. As a result of this, they requested that the TCDO be extended a further year.
United States
Methiopropamine is not scheduled at the federal level in the United States.
Florida
Methiopropamine is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.