MDPHP

MDPHP
Legal status
Legal status	CA: Schedule I; DE: NpSG (Industrial and scientific use only); UK: Class B; Illegal in Japan and Hungary;
Identifiers
	IUPAC name 1-(2H-1,3-Benzodioxol-5-yl)-2-(pyrrolidin-1-yl)hexan-1-one;
CAS Number	776994-64-0;
PubChem CID	119057580;
ChemSpider	52085733;
UNII	7P3X2C24CS;
CompTox Dashboard (EPA)	DTXSID701018396 ;
Chemical and physical data
Formula	C17H23NO3
Molar mass	289.375 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCC(C(=O)C1=CC2=C(C=C1)OCO2)N3CCCC3;
	InChI 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

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.^[8]^[9]

Legal status

MDPHP is specifically listed as a controlled substance in Japan ^[10] and Hungary,^[11] 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.^[12] Another case has been reported, involving a 30-years-old male cocaine consumer, found dead on July 20th, 2023, in Florence, Italy.^[13]

References

^ DE 1545591, Koeppe H, Zeile K, Ludwig G, "Patent DE - Verfahren zur Herstellung von α-Aminoketonen mit heterocyclischer Aminogruppe", issued 28 May 1965
^ "Monkey Dust drug use 'an epidemic', emergency workers warn". BBC. 10 August 2018. Retrieved 16 August 2018.
^ Roberts M. Monkey dust drug clampdown could be coming in UK. BBC News, 11 May 2023
^ 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.
^ 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.
^ 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.
^ 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.
^ Kolaczynska KE, Thomann J, Hoener MC, Liechti ME (July 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.
^ Bassi M, Bilel S, Tirri M, Corli G, Di Rosa F, Gregori A, et al. (July 2024). "The synthetic cathinones MDPHP and MDPV: Comparison of the acute effects in mice, in silico ADMET profiles and clinical reports". Neurotoxicology. 103: 230–255. doi:10.1016/j.neuro.2024.06.014. PMID 38955288.
^ "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.
^ "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).
^ 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.
^ Croce EB, Dimitrova A, Di Milia MG, Pierotti S, Arillotta D, Barbaresi M, et al. (February 2025). "Postmortem distribution of MDPHP in a fatal intoxication case". Journal of Analytical Toxicology. 49 (2): 137–141. doi:10.1093/jat/bkae092. PMC 11982668. PMID 39604091.

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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.

[pmid28895757-6] 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 KE, Thomann J, Hoener MC, Liechti ME (July 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] Bassi M, Bilel S, Tirri M, Corli G, Di Rosa F, Gregori A, et al. (July 2024). "The synthetic cathinones MDPHP and MDPV: Comparison of the acute effects in mice, in silico ADMET profiles and clinical reports". Neurotoxicology. 103: 230–255. doi:10.1016/j.neuro.2024.06.014. PMID 38955288.

[10] "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.

[11] "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).

[12] 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.

[13] Croce EB, Dimitrova A, Di Milia MG, Pierotti S, Arillotta D, Barbaresi M, et al. (February 2025). "Postmortem distribution of MDPHP in a fatal intoxication case". Journal of Analytical Toxicology. 49 (2): 137–141. doi:10.1093/jat/bkae092. PMC 11982668. PMID 39604091.

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v t e Stimulants
Adamantanes	Adapromine Amantadine Bromantane Memantine Rimantadine
Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Istradefylline Paraxanthine SCH-58261 Theobromine Theophylline
Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane
Ampakines	CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram
Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine
Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958
Cathinones	3-FMC 3-MMC 3,4-DMMC 4-BMC 4-CMC 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-Methylpentedrone Amfepramone Benzedrone Buphedrone Bupropion Butylone Cathinone Dimethylcathinone Ethcathinone Ethylone Flephedrone Hexedrone Isoethcathinone Mephedrone Methcathinone Methedrone Methylenedioxycathinone Methylone Mexedrone N-Ethylbuphedrone N-Ethylhexedrone Pentedrone Pentylone Phthalimidopropiophenone
Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538
Convulsants	Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone
Eugeroics	Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil
Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-MMA 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Camfetamine Cathine Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethylnorepinephrine Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Fludorex Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methoxyphenamine MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine
Phenylmorpholines	3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine
Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 JJC8-088 MeOPP MBZP oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate Serdexmethylphenidate SCH-5472
Pyrrolidines	2-Diphenylmethylpyrrolidine 4-Cl-PVP 5-DBFPV α-PPP α-PBP α-PCYP α-PHiP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone
Racetams	Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide
Tropanes	4-fluorotropacocaine 4'-Fluorococaine Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33
Tryptamines	4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT
Others	2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine
ATC code: N06B

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Legal status	CA: Schedule I DE: NpSG (Industrial and scientific use only) UK: Class B Illegal in Japan and Hungary
Identifiers
IUPAC name 1-(2H-1,3-Benzodioxol-5-yl)-2-(pyrrolidin-1-yl)hexan-1-one
CAS Number	776994-64-0
PubChem CID	119057580
ChemSpider	52085733
UNII	7P3X2C24CS
CompTox Dashboard (EPA)	DTXSID701018396
Chemical and physical data
Formula	C₁₇H₂₃NO₃
Molar mass	289.375 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCC(C(=O)C1=CC2=C(C=C1)OCO2)N3CCCC3
InChI 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