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MDPHP

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3',4'-Methylenedioxy-α-pyrrolidinohexiophenone
Legal status
Legal status
Identifiers
  • 1-(2H-1,3-Benzodioxol-5-yl)-2-(pyrrolidin-1-yl)hexan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H23NO3
Molar mass289.375 g·mol−1
3D model (JSmol)
  • CCCCC(C(=O)C1=CC2=C(C=C1)OCO2)N3CCCC3
  • InChI=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
  • Key:OBLFRFGUZZRECT-UHFFFAOYSA-N

MDPHP (3',4'-Methylenedioxy-α-pyrrolidinohexiophenone) is a stimulant of the cathinone class originally developed in the 1960s,[1] which has been reported as a novel designer drug. In the UK its slang name is monkey dust.[2][3] 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.[4][5][6][7]

Pharmacology

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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.[8]

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MDPHP is specifically listed as a controlled substance in Japan [9] and Hungary,[10] and is controlled under analogue provisions in a number of other jurisdictions.

Documented fatalities

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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.[11] Another case has been reported, involving a 30-years-old male cocaine consumer, found dead on July 20th, 2023, in Florence, Italy; MDPHP and alpha-PHP were the only psychoactive substance found. [12]

See also

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References

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  1. ^ DE 1545591, Koeppe H, Zeile K, Ludwig G, "Patent DE - Verfahren zur Herstellung von α-Aminoketonen mit heterocyclischer Aminogruppe", issued 28 May 1965 
  2. ^ "Monkey Dust drug use 'an epidemic', emergency workers warn". BBC. 10 August 2018. Retrieved 16 August 2018.
  3. ^ Roberts M. Monkey dust drug clampdown could be coming in UK. BBC News, 11 May 2023
  4. ^ Zaitsu K, Katagi M, Tsuchihashi H, Ishii A (2013). "Recently abused synthetic cathinones, α-pyrrolidinophenone derivatives: A review of their pharmacology, acute toxicity, and metabolism". Forensic Toxicology. 32: 1–8. doi:10.1007/s11419-013-0218-1. S2CID 25604845.
  5. ^ Kaizaki-Mitsumoto A, Noguchi N, Yamaguchi S, Odanaka Y, Matsubayashi S, Kumamoto H, et al. (January 2016). "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". Forensic Toxicology. 34 (1): 108–14. doi:10.1007/s11419-015-0293-6. S2CID 45890497.
  6. ^ Beck O, Bäckberg M, Signell P, Helander A (April 2018). "Intoxications in the STRIDA project involving a panorama of psychostimulant pyrovalerone derivatives, MDPV copycats". Clinical Toxicology. 56 (4). Philadelphia, Pa.: 256–263. doi:10.1080/15563650.2017.1370097. PMID 28895757. S2CID 3401681.
  7. ^ Fowble KL, Shepard JR, Musah RA (March 2018). "Identification and classification of cathinone unknowns by statistical analysis processing of direct analysis in real time-high resolution mass spectrometry-derived "neutral loss" spectra". Talanta. 179: 546–553. doi:10.1016/j.talanta.2017.11.020. PMID 29310273.
  8. ^ Kolaczynska K, Thomann J, Hoener M, Liechti M (2021). "The Pharmacological Profile of Second Generation Pyrovalerone Cathinones and Related Cathinone Derivative". International Journal of Molecular Sciences. 22 (15): 8277. doi:10.3390/ijms22158277. PMC 8348686. PMID 34361040.
  9. ^ "指定薬物名称・構造式一覧（平成27年9月16日現在）" [List of designated drug names and structural formulas (as of September 16, 2015)] (PDF) (in Japanese). 厚生労働省 (Ministry of Health, Labour and Welfare). 16 September 2015. Retrieved 8 October 2015.
  10. ^ "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" [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.] (PDF) (in Hungarian).
  11. ^ Di Candia D, Boracchi M, Ciprandi B, Giordano G, Zoja R (September 2022). "A unique case of death by MDPHP with no other co-ingestion: a forensic toxicology case". International Journal of Legal Medicine. 136 (5): 1291–1296. doi:10.1007/s00414-022-02799-w. PMC 9375735. PMID 35169902.
  12. ^ NEWS-D "NEWS-D_16_24_Allerta di grado 3_decesso_MDPHP" July 16th, 2024 by the National Early Warning System on Drugs
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