Methiopropamine
Structural analog of methamphetamine
From Wikipedia, the free encyclopedia
Methiopropamine (MPA), also known as N-methylthiopropamine, is an organic compound structurally related to methamphetamine.[2] Originally reported in 1942, the molecule consists of a thiophene group with an alkyl amine substituent at the 2-position.[2][3] It appeared for public sale in the United Kingdom in December 2010 as a "research chemical" or "legal high", recently branded as Blow.[4] It has limited popularity as a recreational stimulant.[2][5][unreliable source?]
- BR: Class F2 (Prohibited psychotropics)[1]
- DE: Anlage I [citation needed]
- UK: Class B
- US: Schedule I
- Illegal in China, Finland, Florida
- 801156-47-8
7464-94-0 (hydrochloride)
| |
 | |
| Clinical data | |
|---|---|
| Other names | MPA; N-Methylthiopropamine; Methiopropamine; Methedrene; Syndrax |
| ATC code | |
| Legal status | |
| Legal status |
|
| Identifiers | |
| |
| CAS Number |
|
| PubChem CID | |
| ChemSpider | |
| UNII | |
| KEGG | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C8H13NS |
| Molar mass | 155.26 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
  (what is this?) (verify) | |
Pharmacology
Methiopropamine functions as a norepinephrine–dopamine reuptake inhibitor (NDRI) 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.[6][7]
Methiopropamine has the potential for significant acute toxicity with cardiovascular, gastrointestinal, and psychotic symptoms.[8]
Metabolism
For N-alkyl amphetamines, deamination and N-dealkylation are the major elimination pathways and renal excretion is a minor one.[9]
Methiopropamine is metabolized into active thiopropamine, 4-hydroxymethiopropamine and thiophene S-oxides.[10][11] 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.[12][13]
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.[14] Methiopropamine is off-white, yellowish powder.[15]
Legal status
China
As of October 2015 MPA is a controlled substance in China.[16]
Finland
Methiopropamine is illegal in Finland, it is scheduled in "government decree on narcotic substances, preparations and plants".[17]
Germany
Methiopropamine is explicitly illegal in Germany. [citation needed]
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[18] 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.[19] 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.[20]
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.[21] 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.[22]
Florida
Methiopropamine is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[23]
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. [citation needed]
See also
- 5-MMPA
- α-Pyrrolidinopentiothiophenone (α-PVT)
- Thiopropamine, demethylated counterpart
- Propylhexedrine, another ring substituted stimulant used as over-the-counter decongestant
- Thiothinone