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Methiopropamine

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Title: Methiopropamine  
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Subject: Thiopropamine, Camfetamine, MPA, Cyclopentamine, Designer drugs
Collection: Amines, Designer Drugs, Ethylamines, Norepinephrine-Dopamine Reuptake Inhibitors, Stimulants, Thiophenes
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Methiopropamine

Methiopropamine
Systematic (IUPAC) name
1-(thiophen-2-yl)-2-methylaminopropane
Clinical data
Legal status
Identifiers
CAS Registry Number  N
7464-94-0 (hydrochloride)
ATC code N06AA
PubChem CID:
ChemSpider  YesY
Synonyms MPA; Methiopropamine; Methedrene; Syndrax
Chemical data
Formula C8H13NS
Molecular mass 155.261 g/mol
 N   

Methiopropamine (MPA) is a thiophene ring-based structural analog of methamphetamine originally reported in 1942.[1] 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.[2] It has limited popularity as a recreational stimulant.[3]

Contents

  • Pharmacology 1
  • Metabolism 2
  • Synthesis 3
  • Legal status 4
    • China 4.1
    • Finland 4.2
    • Germany 4.3
    • United States 4.4
      • Florida 4.4.1
  • See also 5
  • References 6

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.[4]

Metabolism

Methiopropamine metabolism is somewhat similar to methamphetamine. Hydroxylation, demethylation and deamination are in common. Formation of thiophene S-oxide is different, as is the end product which will probably be (substituted) thiophene-2-carboxylic acid. It is then excreted in urine. Compounds on red are inactive.

For N-alkyl amphetamines deamination and N-dealkylation are the major elimination pathways and renal excretion is a minor one.[5] Methiopropamine is metabolized into active thiopropamine, 4-hydroxymethiopropamine and thiophene S-oxides.[6][7] 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.[8][9]

Thiophene-2-carboxylic acid should be 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.[10]

Four-step synthesis of racemic methiopropamine from (thiophen-2-yl)magnesium bromide.

Legal status

China

As of October 2015 MPA is a controlled substance in China.[11]

Finland

Methiopropamine is illegal in Finland.

Germany

Methiopropamine is explicitly illegal in Germany.

United States

Methiopropamine is not scheduled at the federal level in the United States,[12] but it could be considered an analog of methamphetamine, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act. Methiopropamine's structure differs from methamphetamine's structure significantly more than with previous successful prosecutions under the same law.

Florida

Methiopropamine is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[13]

See also

References

  1. ^
  2. ^
  3. ^ Methiopropamine Thread at UKChemicalResearch.org
  4. ^
  5. ^
  6. ^
  7. ^
  8. ^
  9. ^
  10. ^
  11. ^
  12. ^ 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.
  13. ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
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