Chemistry:3',4'-Methylenedioxy-α-pyrrolidinobutiophenone

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Short description: Stimulant drug
3',4'-Methylenedioxy-α-pyrrolidinobutyrophenone
3',4'-Methylenedioxy-α-pyrrolidinobutiophenone.svg
3',4'-Methylenedioxy-α-pyrrolidinobutyrophenone.png
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC15H19NO3
Molar mass261.321 g·mol−1
3D model (JSmol)

3',4'-Methylenedioxy-α-pyrrolidinobutyrophenone (MDPBP) is a stimulant of the cathinone class developed in the 1960s,[1][2] which has been reported as a novel designer drug.[3][4] MDPBP is sometimes sold under the name "NRG-1" as a mixture with other cathinone derivatives, including flephedrone, pentylone, MαPPP and its higher homologue MDPV.[5] As with other cathinones, MDPBP has been shown to have reinforcing effects in rats.[6]

The main metabolic steps are thought to be demethylenation followed by methylation of one hydroxy group, aromatic and side chain hydroxylation, oxidation of the pyrrolidine ring to the corresponding lactam as well as ring opening to the corresponding carboxylic acid. CYP2C19 and CYP2D6 have been identified as the isoenzymes mainly responsible for demethylenation.[7]

Legal Status

(As of October 2015) MDPBP is a controlled substance in Poland and China.[8]

See also

References

  1. ↑ Koeppe H, Zeile K, Ludwig G, "Verfahren zur Herstellung von α-Aminoketonen mit heterocyclischer Aminogruppe", DE patent 1545591, published 28 May 1965, issued 7 August 1969, assigned to Boehringer Ingelheim
  2. ↑ ""Deconstruction" of the abused synthetic cathinone methylenedioxypyrovalerone (MDPV) and an examination of effects at the human dopamine transporter". ACS Chemical Neuroscience 4 (12): 1524–9. December 2013. doi:10.1021/cn4001236. PMID 24116392. 
  3. ↑ "Spectroscopic characterization of 3,4-methylenedioxypyrrolidinobutyrophenone: a new designer drug with α-pyrrolidinophenone structure". Forensic Science International 209 (1–3): 126–32. June 2011. doi:10.1016/j.forsciint.2011.01.016. PMID 21316166. 
  4. ↑ "Determination of MDPBP in postmortem blood samples by gas chromatography coupled with mass spectrometry". Monatshefte für Chemie 147 (8): 1415–1421. August 2016. doi:10.1007/s00706-016-1780-0. PMID 27546909. 
  5. ↑ "Analysis of NRG 'legal highs' in the UK: identification and formation of novel cathinones". Drug Testing and Analysis 3 (9): 569–75. September 2011. doi:10.1002/dta.204. PMID 21960541. 
  6. ↑ "Relative reinforcing effects of second-generation synthetic cathinones: Acquisition of self-administration and fixed ratio dose-response curves in rats". Neuropharmacology 134 (Pt A): 28–35. May 2018. doi:10.1016/j.neuropharm.2017.08.018. PMID 28811192. 
  7. ↑ "The in vivo and in vitro metabolism and the detectability in urine of 3',4'-methylenedioxy-alpha-pyrrolidinobutyrophenone (MDPBP), a new pyrrolidinophenone-type designer drug, studied by GC-MS and LC-MS(n.)". Drug Testing and Analysis 6 (7–8): 746–56. July–August 2014. doi:10.1002/dta.1559. PMID 24124065. 
  8. ↑ "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 zh). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 




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