MDPHP

{{Short description|Chemical compound}}

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{{drugbox

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

| image = MDPHP.svg

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

| CAS_number = 776994-64-0

| ATC_prefix =

| 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

| SMILES = CCCCC(C(=O)C1=CC2=C(C=C1)OCO2)N3CCCC3

| bioavailability =

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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 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,{{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}} which has been reported as a novel designer drug. In the UK its slang name is monkey dust.{{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}}[https://www.bbc.com/news/health-65556046 Roberts M. Monkey dust drug clampdown could be coming in UK. BBC News, 11 May 2023] 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.{{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 }}{{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 }}{{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 }}{{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 }}

Pharmacology

File:Appearance of MDPHP powder.jpg

MDPHP acts as a potent norepinephrine-dopamine reuptake inhibitor. The IC50 values for MDPHP are 0.06 μM at NET, 0.05 μM at DAT and 9 μM at SERT.{{Cite journal |vauthors=Kolaczynska K, Thomann J, Hoener M, Liechti M |title=The Pharmacological Profile of Second Generation Pyrovalerone Cathinones and Related Cathinone Derivative |journal=International Journal of Molecular Sciences |date=2021 |volume=22 |issue=15 |page=8277 |doi=10.3390/ijms22158277 |doi-access=free |pmid=34361040|pmc=8348686 }}

Legal status

MDPHP is specifically listed as a controlled substance in Japan {{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}} and Hungary,{{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 }} 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.{{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 }}

Another case has been reported, involving a 30-years-old male cocaine consumer, found dead on July 20th, 2023, in Florence, Italy.{{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 }}

See also

References

{{Reflist}}

{{Stimulants}}

{{Monoamine reuptake inhibitors}}

{{Phenethylamines}}

Category:Butyl compounds

Category:Designer drugs

Category:Methylenedioxyphenethylamines

Category:Pyrrolidinophenones

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