MDPHP

{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | IUPAC_name = 1-(2''H''-1,3-Benzodioxol-5-yl)-2-(pyrrolidin-1-yl)hexan-1-one | image = MDPHP.svg | image_class = skin-invert-image | width = 250px | image2 = 3',4'-Methylenedioxy-α-pyrrolidinohexiophenone.png | image_class2 = bg-transparent | width2 = 250px | CAS_number = 776994-64-0 | ATC_prefix = None | ATC_suffix = | PubChem = 119057580 | UNII = 7P3X2C24CS | DrugBank = | ChemSpiderID = 52085733 | C=17 | H=23 | N=1 | O=3 | SMILES = CCCCC(N1CCCC1)C(=O)c2ccc3OCOc3c2 | StdInChI = 1S/C17H23NO3/c1-2-3-6-14(18-9-4-5-10-18)17(19)13-7-8-15-16(11-13)21-12-20-15/h7-8,11,14H,2-6,9-10,12H2,1H3 | StdInChIKey = OBLFRFGUZZRECT-UHFFFAOYSA-N | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | pregnancy_AU =  | pregnancy_US =  | pregnancy_category= | legal_AU =  | legal_CA = Schedule I | legal_DE = NpSG | legal_UK = Class B | legal_US =  | legal_status = Illegal in Japan and Hungary | routes_of_administration = | UNII_Ref = {{fdacite|correct|FDA}} }}

'''MDPHP''' ('''3',4'-Methylenedioxy-α-pyrrolidinohexiophenone''') is a stimulant of the cathinone class originally developed in the 1960s,<ref>{{cite patent | country = DE | number = 1545591 | inventor = Koeppe H, Zeile K, Ludwig G |title=Patent DE - Verfahren zur Herstellung von α-Aminoketonen mit heterocyclischer Aminogruppe |url=https://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19690807&DB=&locale=en_EP&CC=DE&NR=1545591A1&KC=A1|gdate =28 May 1965}}</ref> which has been reported as a novel designer drug. In the UK its slang name is '''''monkey dust'''''.<ref>{{cite web |url= https://www.bbc.com/news/uk-england-stoke-staffordshire-45144531 |title= Monkey Dust drug use 'an epidemic', emergency workers warn |work= BBC |date= 10 August 2018 |access-date= 16 August 2018}}</ref><ref>[https://www.bbc.com/news/health-65556046 Roberts M. Monkey dust drug clampdown could be coming in UK. ''BBC News'', 11 May 2023]</ref> It is closely related to the potent stimulant MDPV though with slightly milder effects, and has been used as an alternative in some countries following the banning of MDPV.<ref>{{cite journal | vauthors = Zaitsu K, Katagi M, Tsuchihashi H, Ishii A |s2cid=25604845|doi=10.1007/s11419-013-0218-1|title=Recently abused synthetic cathinones, α-pyrrolidinophenone derivatives: A review of their pharmacology, acute toxicity, and metabolism|journal=Forensic Toxicology|volume=32|pages=1–8|year=2013 }}</ref><ref>{{cite journal | vauthors = Kaizaki-Mitsumoto A, Noguchi N, Yamaguchi S, Odanaka Y, Matsubayashi S, Kumamoto H, Fukuhara K, Funada M, Wada K, Numazawa S | s2cid = 45890497 | title = Three 25-NBOMe-type drugs, three other phenethylamine-type drugs (25I-NBMD, RH34, and escaline), eight cathinone derivatives, and a phencyclidine analog MMXE, newly identified in ingredients of drug products before they were sold on the drug market. | journal = Forensic Toxicology | date = January 2016 | volume = 34 | issue = 1 | pages = 108–14 | doi = 10.1007/s11419-015-0293-6 }}</ref><ref name="pmid28895757">{{cite journal | vauthors = Beck O, Bäckberg M, Signell P, Helander A | s2cid = 3401681 | title = Intoxications in the STRIDA project involving a panorama of psychostimulant pyrovalerone derivatives, MDPV copycats | journal = Clinical Toxicology | location = Philadelphia, Pa. | volume = 56 | issue = 4 | pages = 256–263 | date = April 2018 | pmid = 28895757 | doi = 10.1080/15563650.2017.1370097 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Fowble KL, Shepard JR, Musah RA | title = Identification and classification of cathinone unknowns by statistical analysis processing of direct analysis in real time-high resolution mass spectrometry-derived "neutral loss" spectra | journal = Talanta | volume = 179 | pages = 546–553 | date = March 2018 | pmid = 29310273 | doi = 10.1016/j.talanta.2017.11.020 | doi-access = free }}</ref>

== Pharmacology == thumb|165px|MDPHP powder MDPHP acts as a potent norepinephrine-dopamine reuptake inhibitor. The IC50 values for MDPHP are 60-935 nM at NET, 8.4-50 nM at DAT and 9000 nM at SERT.<ref>{{cite journal | vauthors = Kolaczynska KE, Thomann J, Hoener MC, Liechti ME | title = The Pharmacological Profile of Second Generation Pyrovalerone Cathinones and Related Cathinone Derivative | journal = International Journal of Molecular Sciences | volume = 22 | issue = 15 | page = 8277 | date = July 2021 | pmid = 34361040 | pmc = 8348686 | doi = 10.3390/ijms22158277 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Bassi M, Bilel S, Tirri M, Corli G, Di Rosa F, Gregori A, Alkilany AM, Rachid O, Roda E, De Luca F, Papa P, Buscaglia E, Zauli G, Locatelli CA, Marti M | title = The synthetic cathinones MDPHP and MDPV: Comparison of the acute effects in mice, in silico ADMET profiles and clinical reports | journal = Neurotoxicology | volume = 103 | pages = 230–255 | date = July 2024 | pmid = 38955288 | doi = 10.1016/j.neuro.2024.06.014 | hdl = 11392/2573094 | hdl-access = free }}</ref>

== Legal status == MDPHP is specifically listed as a controlled substance in Japan <ref>{{cite web | url=http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf | title=指定薬物名称・構造式一覧（平成27年9月16日現在）| trans-title = List of designated drug names and structural formulas (as of September 16, 2015) | publisher=厚生労働省 (Ministry of Health, Labour and Welfare) | date=16 September 2015 | language=Japanese | access-date=8 October 2015}}</ref> and Hungary,<ref>{{cite web | title = A Daath.hu kiegészítése a BSZKI "designer jogi listáján" nem szereplő, de a C-lista 1.-4. szerkezeti leírásainak megfelelő, illetve a C-lista 5. felsorolásában szereplő néhány anyagról | trans-title = The addition to Daath.hu is not included in the "designer legal list" of the BSZKI, but C-list 1.-4. and some of the substances in list 5 of list C. | language = Hungarian | url = http://www.daath.hu/incoming/designer_jogi_lista_20150903_BSZKI_Daath_kieg.pdf }}</ref> and is controlled under analogue provisions in a number of other jurisdictions.

== Documented fatalities == A case of a "fatal acute intoxication caused by MDPHP" in a 48 year old male was reported in February 2022 by physicians at an Italian hospital.<ref>{{cite journal | vauthors = Di Candia D, Boracchi M, Ciprandi B, Giordano G, Zoja R | title = A unique case of death by MDPHP with no other co-ingestion: a forensic toxicology case | journal = International Journal of Legal Medicine | volume = 136 | issue = 5 | pages = 1291–1296 | date = September 2022 | pmid = 35169902 | pmc = 9375735 | doi = 10.1007/s00414-022-02799-w }}</ref> Another case has been reported, involving a 30-years-old male cocaine consumer, found dead on July 20th, 2023, in Florence, Italy.<ref>{{cite journal | vauthors = Croce EB, Dimitrova A, Di Milia MG, Pierotti S, Arillotta D, Barbaresi M, Focardi M, Vaiano F | title = Postmortem distribution of MDPHP in a fatal intoxication case | journal = Journal of Analytical Toxicology | volume = 49 | issue = 2 | pages = 137–141 | date = February 2025 | pmid = 39604091 | pmc = 11982668 | doi = 10.1093/jat/bkae092 }}</ref>

== References == {{Reflist}}

Category:Butyl compounds Category:Designer drugs Category:Methylenedioxycathinones Category:Pyrrolidinophenones