There is a four-step synthesis of methiopropamine. It begins with (thiophen-2-yl)magnesium bromide, which is reacted withpropylene oxide, yielding 1-(thiophen-2-yl)-2-hydroxypropane which is reacted withphosphorus tribromide, yielding 1-(thiophen-2-yl)-2-bromopropane which is finally reacted withmethylamine, yielding 1-(thiophen-2-yl)-2-methylaminopropane.[14] Methiopropamine is off-white, yellowish powder.[15]
Four-step synthesis of racemic methiopropamine from (thiophen-2-yl)magnesium bromide.
Following the ban onethylphenidate, authorities noticed an increase in methiopropamine use by injecting users. TheACMD suggested it be banned on 18 November 2015[18] as it had similar effects to ethylphenidate. The government enacted atemporary 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.
Methiopropamine is scheduled at the federal level in theUnited 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]
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]
^abcBunaim MK, Damanhuri HA, Yow HY, Yaakob NS, Makmor-Bakry M, Azmi N (July 2024). "Understanding methiopropamine, a new psychoactive substance: an in-depth review on its chemistry, pharmacology and implications to human health".Int J Legal Med.138 (4):1295–1306.doi:10.1007/s00414-024-03201-7.PMID38424369.
^Angelov D, O'Brien J, Kavanagh P (March 2013). "The syntheses of 1-(2-thienyl)-2-(methylamino) propane (methiopropamine) and its 3-thienyl isomer for use as reference standards".Drug Testing and Analysis.5 (3):145–9.doi:10.1002/dta.298.PMID21770051.
^Yoon HS, Cai WT, Lee YH, Park KT, Lee YS, Kim JH (September 2016). "The expression of methiopropamine-induced locomotor sensitization requires dopamine D2, but not D1, receptor activation in the rat".Behavioural Brain Research.311:403–407.doi:10.1016/j.bbr.2016.05.060.PMID27265782.S2CID46731570.
^Vree TB, Gorgels JP, Muskens AT, van Rossum JM (September 1971). "Deuterium isotope effects in the metabolism of N-alkylsubstituted amphetamines in man".Clinica Chimica Acta; International Journal of Clinical Chemistry.34 (2):333–44.doi:10.1016/0009-8981(71)90187-2.hdl:2066/142600.PMID5113570.
^Treiber A, Dansette PM, El Amri H, Girault J, Ginderow D, Mornon J, Mansuy D (1997). "Chemical and Biological Oxidation of Thiophene: Preparation and Complete Characterization of Thiophene S-Oxide Dimers and Evidence for Thiophene S-Oxide as an Intermediate in Thiophene Metabolismin Vivo andin Vitro".Journal of the American Chemical Society.119 (7):1565–71.Bibcode:1997JAChS.119.1565T.doi:10.1021/ja962466g.
^Dansette PM, Thang DC, el Amri H, Mansuy D (August 1992). "Evidence for thiophene-S-oxide as a primary reactive metabolite of thiophene in vivo: formation of a dihydrothiophene sulfoxide mercapturic acid".Biochemical and Biophysical Research Communications.186 (3):1624–30.Bibcode:1992BBRC..186.1624D.doi:10.1016/S0006-291X(05)81594-3.PMID1510686.
^"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 fromthe original on 1 October 2015. Retrieved1 October 2015.
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