Methiopropamine

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Methiopropamine
N06AA
Legal status
Legal status
Identifiers
  • 1-(thiophen-2-yl)-2-methylaminopropane
JSmol)
  • CNC(C)CC1=CC=CS1
  • InChI=1S/C8H13NS/c1-7(9-2)6-8-4-3-5-10-8/h3-5,7,9H,6H2,1-2H3 checkY
  • Key:HPHUWHKFQXTZPS-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Methiopropamine (MPA) is an organic compound structurally related to methamphetamine. Originally reported in 1942, the molecule consists of a thiophene group with an alkyl amine substituent at the 2-position.[2] It appeared for public sale in the UK in December 2010 as a "research chemical" or "legal high", recently branded as Blow.[3] It has limited popularity as a recreational stimulant.[4][unreliable source?]

Pharmacology

Methiopropamine functions as a

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.[5][6]

Methiopropamine has the potential for significant acute toxicity with cardiovascular, gastrointestinal, and psychotic symptoms.[7]

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,

renal excretion is a minor one.[8]

Methiopropamine is

thiopropamine, 4-hydroxymethiopropamine and thiophene S-oxides.[9][10] 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.[11][12]

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.[13]

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.[14]

Finland

Methiopropamine is illegal in Finland.[citation needed]

Germany

Methiopropamine is explicitly illegal in Germany.

United Kingdom

Following the ban on

ACMD suggested it be banned on 18 November 2015[15] 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.[16] 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.[17]

Methiopropanine was made a Class B controlled drug under the Misuse of Drugs Act 1971 (as amended) (Amendment)(No.2) Order 2017 [SI 2017/1114], this came into effect on the 27th of November 2017.

United States

Methiopropamine is scheduled at the federal level in the United States.[18] The DEA had planned to place methiopropamine in Schedule I of Controlled Substances and was accepting public comments until October 4, 2021. Later, the compound was placed in Schedule I.[19]

Florida

Methiopropamine is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[20]

Tasmania (Australia) Methiopropamine is a "controlled substance" and therefore an "illegal drug" to import, possess or sell/traffic in without express authority of the relevant government agency.

See also

References

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. doi:10.1021/ja01255a001
    .
  3. PMID 21770051
    .
  4. ^ "Methiopropamine Thread". UKChemicalResearch.org. Archived from the original on 2015-07-04. Retrieved 2016-06-09.
  5. PMID 23261499
    .
  6. S2CID 46731570
    .
  7. PMID 24706157
    .
  8. PMID 5113570
    .
  9. doi:10.1021/ja962466g
    .
  10. PMID 1510686
    .
  11. PMID 9076658
    .
  12. S2CID 5470554
    .
  13. ^ Casale JF, Hays PA (2011). "Methiopropamine: An Analytical Profile" (PDF). Microgram Journal. 8 (2): 53–57.
  14. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  15. ^ Advisory Council on the Misuse of Drugs (25 November 2015). "Methiopropamine (MPA): A review of the evidence of use and harm" (PDF). UK Home Office. Retrieved 27 November 2015.
  16. ^ "The Misuse of Drugs Act 1971 (Temporary Class Drug) (No. 3) Order 2015". UK Government. 23 November 2015.
  17. ^ "Re: Temporary Class Drug Order on methiopropamine". 2016. Retrieved 2016-11-28.
  18. ^ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  19. ^ "Federal Register". Federal Register. National Archives. December 9, 2022. Retrieved December 28, 2022.
  20. ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
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