3',4'-Methylenedioxy-α-pyrrolidinobutiophenone

{{Short description|Stimulant drug}}

{{drugbox

| IUPAC_name = 1-(2H-1,3-Benzodioxol-5-yl)-2-(pyrrolidin-1-yl)butan-1-one

| image = 3',4'-Methylenedioxy-α-pyrrolidinobutiophenone.svg

| image2 = 3',4'-Methylenedioxy-α-pyrrolidinobutyrophenone.png

| CAS_number = 784985-33-7

| ATC_prefix =

| ATC_suffix =

| PubChem = 71300672

| DrugBank =

| ChemSpiderID = 52084589

| C=15|H=19|N=1|O=3

| smiles = CCC(C(=O)C1=CC2=C(C=C1)OCO2)N3CCCC3

| StdInChI = 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

| StdInChIKey = OLVLMDVPMCIBQW-UHFFFAOYSA-N

| bioavailability =

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| metabolism =

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| pregnancy_AU =

| pregnancy_US =

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| legal_AU =

| legal_CA = Schedule I

| legal_DE = NpSG

| legal_UK = Class B

| legal_US =

| legal_status = Illegal in China and Poland

| routes_of_administration =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 979L917V7T

}}

3',4'-Methylenedioxy-α-pyrrolidinobutyrophenone (MDPBP) is a stimulant of the cathinone class developed in the 1960s,{{cite patent | inventor = Koeppe H, Zeile K, Ludwig G | assign1 = Boehringer Ingelheim |title = Verfahren zur Herstellung von α-Aminoketonen mit heterocyclischer Aminogruppe | country = DE | number = 1545591 | pubdate = 28 May 1965 | gdate = 7 August 1969}}{{cite journal | vauthors = Kolanos R, Solis E, Sakloth F, De Felice LJ, Glennon RA | title = "Deconstruction" of the abused synthetic cathinone methylenedioxypyrovalerone (MDPV) and an examination of effects at the human dopamine transporter | journal = ACS Chemical Neuroscience | volume = 4 | issue = 12 | pages = 1524–9 | date = December 2013 | pmid = 24116392 | pmc = 3867964 | doi = 10.1021/cn4001236 }} which has been reported as a novel designer drug.{{cite journal | vauthors = Westphal F, Junge T, Klein B, Fritschi G, Girreser U | title = Spectroscopic characterization of 3,4-methylenedioxypyrrolidinobutyrophenone: a new designer drug with α-pyrrolidinophenone structure | journal = Forensic Science International | volume = 209 | issue = 1–3 | pages = 126–32 | date = June 2011 | pmid = 21316166 | doi = 10.1016/j.forsciint.2011.01.016 }}{{cite journal | vauthors = Wiergowski M, Woźniak MK, Kata M, Biziuk M | title = Determination of MDPBP in postmortem blood samples by gas chromatography coupled with mass spectrometry | journal = Monatshefte für Chemie | volume = 147 | issue = 8 | pages = 1415–1421 | date = August 2016 | pmid = 27546909 | pmc = 4971041 | doi = 10.1007/s00706-016-1780-0 }} 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.{{cite journal | vauthors = Brandt SD, Freeman S, Sumnall HR, Measham F, Cole J | title = Analysis of NRG 'legal highs' in the UK: identification and formation of novel cathinones | journal = Drug Testing and Analysis | volume = 3 | issue = 9 | pages = 569–75 | date = September 2011 | pmid = 21960541 | doi = 10.1002/dta.204 | citeseerx = 10.1.1.687.9467 }} As with other cathinones, MDPBP has been shown to have reinforcing effects in rats.{{cite journal | vauthors = Gannon BM, Galindo KI, Mesmin MP, Sulima A, Rice KC, Collins GT | title = Relative reinforcing effects of second-generation synthetic cathinones: Acquisition of self-administration and fixed ratio dose-response curves in rats | journal = Neuropharmacology | volume = 134 | issue = Pt A | pages = 28–35 | date = May 2018 | pmid = 28811192 | pmc = 5809320 | doi = 10.1016/j.neuropharm.2017.08.018 }}

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.{{cite journal | vauthors = Meyer MR, Mauer S, Meyer GM, Dinger J, Klein B, Westphal F, Maurer HH | title = 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.) | journal = Drug Testing and Analysis | volume = 6 | issue = 7–8 | pages = 746–56 | date = July–August 2014 | pmid = 24124065 | doi = 10.1002/dta.1559 }}