Propylone

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| class = Monoamine releasing agent; Monoamine reuptake inhibitor

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| CAS_number = 201474-93-3

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| PubChem = 85764579

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| ChemSpiderID = 129433781

| UNII = TBJ4S8YF37

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| synonyms = 3,4-Methylenedioxy-N-propylcathinone; MD-PrC; PrONE; bk-3,4-MDPA

| IUPAC_name = 1-(1,3-benzodioxol-5-yl)-2-(propylamino)propan-1-one

| C=13 | H=17 | N=1 | O=3

| SMILES = CCCNC(C)C(=O)C1=CC2=C(C=C1)OCO2

| StdInChI = 1S/C13H17NO3/c1-3-6-14-9(2)13(15)10-4-5-11-12(7-10)17-8-16-11/h4-5,7,9,14H,3,6,8H2,1-2H3

| StdInChIKey = YFVKHKCZBSGZPE-UHFFFAOYSA-N

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Propylone, also known as 3,4-methylenedioxy-N-propylcathinone is a mixed monoamine releasing agent and reupake inhibitor of the cathinone family related to methylone and ethylone.{{cite thesis | vauthors = Sakloth F | degree = Ph.D. | title=Psychoactive synthetic cathinones (or 'bath salts'): Investigation of mechanisms of action | work = Theses and Dissertations | via = VCU Scholars Compass | publisher = Virginia Commonwealth University | date=11 December 2015 | doi=10.25772/AY8R-PW77 | url=https://scholarscompass.vcu.edu/etd/4041/ | access-date=24 November 2024}}

It acts specifically as a weak partial serotonin–dopamine releasing agent (SDRA) and serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI), with {{Abbrlink|EC₅₀|half-maximal effective concentration}} ({{Abbrlink|E_max|maximal efficacy}}) values for induction of monoamine release of 3,128{{nbsp}}nM (30%) for serotonin and 976{{nbsp}}nM (20%) for dopamine, and {{Abbrlink|IC₅₀|half-maximal inhibitory concentration}} value for monoamine reuptake inhibition of 2,462{{nbsp}}nM for serotonin, 28,540{{nbsp}}nM for norepinephrine, and 1,863{{nbsp}}nM for dopamine.

The drug was first described in the literature in a 1996 patent by Alexander Shulgin and Peyton Jacob III.{{cite patent | country = WO | number = 1996039133 | title = Preparation of novel N-substituted-2-amino-3′,4′-methylenedioxypropiophenones as anti-depressant and anti-parkinsonism agents. | pubdate = 12 December 1996 | inventor = Jacob III P, Shulgin AT | assign1 = Neurobiological Technologies, Inc. }} It was subsequently characterized more thoroughly by 2015 and was encountered as a novel designer drug in Europe by 2016.{{cite web | title=EMCDDA–Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA | website=Europol | date=23 October 2018 | url=https://www.europol.europa.eu/publications-events/publications/emcdda%E2%80%93europol-2016-annual-report-implementation-of-council-decision-2005/387/jha | access-date=11 March 2025}}{{cite journal | vauthors = Liu C, Jia W, Li T, Hua Z, Qian Z | title = Identification and analytical characterization of nine synthetic cathinone derivatives N-ethylhexedrone, 4-Cl-pentedrone, 4-Cl-α-EAPP, propylone, N-ethylnorpentylone, 6-MeO-bk-MDMA, α-PiHP, 4-Cl-α-PHP, and 4-F-α-PHP | journal = Drug Test Anal | volume = 9 | issue = 8 | pages = 1162–1171 | date = August 2017 | pmid = 27863142 | doi = 10.1002/dta.2136 | url = }}{{cite journal | vauthors = Pulver B, Fischmann S, Gallegos A, Christie R | title = EMCDDA framework and practical guidance for naming cathinones | journal = Drug Test Anal | volume = 16 | issue = 12 | pages = 1409–1435 | date = December 2024 | pmid = 38389255 | pmc = 11635063 | doi = 10.1002/dta.3662 | url = }}