3',4'-Methylenedioxy-α-pyrrolidinobutiophenone

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]

3',4'-Methylenedioxy-α-pyrrolidinobutyrophenone
Legal status
Legal status
  • CA: Schedule I
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
  • Illegal in China and Poland
Identifiers
IUPAC name
  • 1-(2H-1,3-Benzodioxol-5-yl)-2-(pyrrolidin-1-yl)butan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC15H19NO3
Molar mass261.321 g·mol−1
3D model (JSmol)
SMILES
  • CCC(C(=O)C1=CC2=C(C=C1)OCO2)N3CCCC3
InChI
  • InChI=1S/C15H19NO3/c1-2-12(16-7-3-4-8-16)15(17)11-5-6-13-14(9-11)19-10-18-13/h5-6,9,12H,2-4,7-8,10H2,1H3
  • Key:OLVLMDVPMCIBQW-UHFFFAOYSA-N

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]

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

See also

References
  1. DE 1545591, Koeppe H, Zeile K, Ludwig G, "Verfahren zur Herstellung von α-Aminoketonen mit heterocyclischer Aminogruppe", published 28 May 1965, issued 7 August 1969, assigned to Boehringer Ingelheim
  2. Kolanos R, Solis E, Sakloth F, De Felice LJ, Glennon RA (December 2013). ""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. doi:10.1021/cn4001236. PMC 3867964. PMID 24116392.
  3. Westphal F, Junge T, Klein B, Fritschi G, Girreser U (June 2011). "Spectroscopic characterization of 3,4-methylenedioxypyrrolidinobutyrophenone: a new designer drug with α-pyrrolidinophenone structure". Forensic Science International. 209 (1–3): 126–32. doi:10.1016/j.forsciint.2011.01.016. PMID 21316166.
  4. Wiergowski M, Woźniak MK, Kata M, Biziuk M (August 2016). "Determination of MDPBP in postmortem blood samples by gas chromatography coupled with mass spectrometry". Monatshefte für Chemie. 147 (8): 1415–1421. doi:10.1007/s00706-016-1780-0. PMC 4971041. PMID 27546909.
  5. Brandt SD, Freeman S, Sumnall HR, Measham F, Cole J (September 2011). "Analysis of NRG 'legal highs' in the UK: identification and formation of novel cathinones". Drug Testing and Analysis. 3 (9): 569–75. CiteSeerX 10.1.1.687.9467. doi:10.1002/dta.204. PMID 21960541.
  6. Gannon BM, Galindo KI, Mesmin MP, Sulima A, Rice KC, Collins GT (May 2018). "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. doi:10.1016/j.neuropharm.2017.08.018. PMC 5809320. PMID 28811192.
  7. Meyer MR, Mauer S, Meyer GM, Dinger J, Klein B, Westphal F, Maurer HH (July–August 2014). "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. 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 Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.


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