Chemical compound
Pharmaceutical compound
MDPHP (3',4'-Methylenedioxy-α-pyrrolidinohexiophenone ) is a stimulant of the cathinone class originally developed in the 1960s,[ 1] designer drug . In the UK its slang name is monkey dust [ 2] [ 3] 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 powder 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]
Legal status
MDPHP is specifically listed as a controlled substance in Japan [ 9] [ 10] 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.[ 11] [ 12]
See also
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 . 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 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 . ^ "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 .
DAT Tooltip Dopamine transporter (DRIs Tooltip Dopamine reuptake inhibitors )
NET Tooltip Norepinephrine transporter (NRIs Tooltip Norepinephrine reuptake inhibitors )
Others: Antihistamines (e.g., brompheniramine , chlorphenamine , pheniramine , tripelennamine )Antipsychotics (e.g., loxapine , ziprasidone )Arylcyclohexylamines (e.g., ketamine , phencyclidine )Dopexamine Ephenidine Ginkgo biloba Indeloxazine Nefazodone Opioids (e.g., desmetramadol , methadone , pethidine (meperidine) , tapentadol , tramadol , levorphanol )
SERT Tooltip Serotonin transporter (SRIs Tooltip Serotonin reuptake inhibitors )
Others: A-80426 Amoxapine Antihistamines (e.g., brompheniramine , chlorphenamine , dimenhydrinate , diphenhydramine , mepyramine (pyrilamine) , pheniramine , tripelennamine )Antipsychotics (e.g., loxapine , ziprasidone )Arylcyclohexylamines (e.g., 3-MeO-PCP , esketamine , ketamine , methoxetamine , phencyclidine )Cyclobenzaprine Delucemine Dextromethorphan Dextrorphan Efavirenz Hypidone Medifoxamine Mesembrine Mifepristone MIN-117 (WF-516) N-Me-5-HT Opioids (e.g., dextropropoxyphene , methadone , pethidine (meperidine) , levorphanol , tapentadol , tramadol )Roxindole
VMATs Tooltip Vesicular monoamine transporters Others
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted
1-Aminomethylindanes (e.g., 2CB-Ind , AMMI , bromojimscaline , jimscaline )2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CJP 2CLisaB 2CLisaH 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g., 3-phenylpiperidine , 3-PPP , OSU-6162 (PNU-96391) , LPH-5 , LPH-48 , Z3517967757 (Z7757) )6-AB AL-1095 Aminochromes (e.g., adrenochrome , adrenolutin )Benzazepines (e.g., fenoldopam , lorcaserin , SCHEMBL5334361 )Benzocyclobutenes (e.g., 2CBCB-NBOMe , bromotomscaline , S33005 , TCB-2 , tomscaline )Benzoxepins (e.g., BBOX , IBOX , TFMBOX )Butyltolylquinuclidine Camfetamine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g., LSD )Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g., NDTDI , RU-27849 , DEIMDHPCA , DEMPDHPCA , DEMPDHPCA-2C-D , RU-27251 )PF-592,379 Phenylcyclopropylamines (e.g., DMCPA , TMT , tranylcypromine )Phenylpiracetams (e.g., phenylpiracetam , MRZ-9547 , RGPU-95 )Pyridopyrroloquinoxalines (e.g., lumateperone , deulumateperone , IHCH-7079 , IHCH-7086 , IHCH-7113 , ITI-1549 )Tetrahydrobenzopyranylamines (e.g., CT-5126 )Tolazoline Tricyclics (e.g., AMDA , AMDH , benzoctamine , dizocilpine , SpAMDA )ZC-B
Related compounds
2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g., 1,3-DMBA Tooltip 1,3-dimethylbutylamine , 1,4-DMAA Tooltip 1,4-dimethylamylamine , heptaminol , iproheptine , isometheptene , methylhexanamine/1,3-DMAA , octodrine , oenethyl , tuaminoheptane )Benzylamines (e.g., benzylamine , α-methylbenzylamine , MDM1EA , ALPHA , M-ALPHA , pargyline )Benzylpiperazines (e.g., benzylpiperazine , MDBZP , fipexide )Cyclohexylaminopropanes (e.g., propylhexedrine , norpropylhexedrine )Cyclopentylaminopropanes (e.g., isocyclamine , cyclopentamine )Phenoxyethylamines (e.g., 3,4,5-trimethoxyphenoxyethylamine , CT-4719 , ORG-37684 )Phenylalkenylamines (e.g., phenylbutenamine )Phenylalkynylamines (e.g., phenylbutynamine )Phenylpiperazines (e.g., 1-phenylpiperazine , mCPP Tooltip meta-chlorophenylpiperazine , TFMPP Tooltip trifluoromethylphenylpiperazine , oMPP Tooltip ortho-methylphenylpiperazine , pFPP Tooltip para-fluorophenylpiperazine , pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g., phenylpropylamine , homo-MDA , homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g., thiopropamine , methiopropamine , thiothinone )
