I catinoni sostituiti sono molecole ad azione stimolante ed entactogena-empatogena, derivati dal catinone.
Sono caratterizzati da un nucleo di fenetilammina con un gruppo alchilico attaccato al carbonio alfa e un gruppo chetone attaccato al carbonio beta, insieme a sostituzioni aggiuntive.Meltzer PC, Butler D, Deschamps JR, Madras BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors. J Med Chem. 2006 Feb 23;49(4):1420-32. Paillet-Loilier M, Cesbron A, Le Boisselier R, Bourgine J, Debruyne D. Emerging drugs of abuse: current perspectives on substituted cathinones. Subst Abuse Rehabil. 2014; 5: 37-52. Simmons SJ, Leyrer-Jackson JM, Oliver CF, Hicks C, Muschamp JW, Rawls SM, Olive MF. DARK Classics in Chemical Neuroscience: Cathinone-Derived Psychostimulants. ACS Chem. Neurosci. 2018; 9(10): 2379-2394. Beck O, Bäckberg M, Signell P, Helander A. Intoxications in the STRIDA project involving a panorama of psychostimulant pyrovalerone derivatives, MDPV copycats. Clin Toxicol (Phila). 2018 Apr;56(4):256-263. Majchrzak M, Celiński R, Kuś P, Kowalska T, Sajewicz M. The newest cathinone derivatives as designer drugs: an analytical and toxicological review. Forensic Toxicol. 2018;36(1):33-50. Il catinone si trova naturalmente nella pianta khat le cui foglie vengono masticate come droga ricreativa.Colzato LS, Ruiz MJ, van den Wildenberg WP, Hommel B. Khat use is associated with impaired working memory and cognitive flexibility. PLoS One. 2011;6(6):e20602. . accesso 2011-07-17.
Elenco dei catinoni sostituiti I derivati possono essere prodotti mediante sostituzioni in quattro posizioni della molecola del catinone:
R 1 = idrogeno o qualsiasi combinazione di uno o più sostituenti alchilici, alcossi, alchilendiossi, aloalchilici o alogenuri R 2 = idrogeno o qualsiasi gruppo alchilico R 3 = idrogeno, qualsiasi gruppo alchilico o incorporazione in una struttura ciclica R 4 = idrogeno, qualsiasi gruppo alchilico o incorporazione in una struttura ciclica
La tabella seguente mostra i derivati importanti che sono stati riportati:Maurer HH, Kraemer T, Springer D, Staack RF. Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis. Ther Drug Monit. 2004 Apr;26(2):127-31. Davis S, Rands-Trevor K, Boyd S, Edirisinghe M. The characterisation of two halogenated cathinone analogues: 3,5-difluoromethcathinone and 3,5-dichloromethcathinone. Forensic Sci Int. 2012 Apr 10;217(1-3):139-45. Błażewicz, A., Bednarek, E., Popławska, M. et al. Identification and structural characterization of synthetic cathinones: N-propylcathinone, 2,4-dimethylmethcathinone, 2,4-dimethylethcathinone, 2,4-dimethyl-α-pyrrolidinopropiophenone, 4-bromo-α-pyrrolidinopropiophenone, 1-(2,3-dihydro-1H-inden-5-yl)-2-(pyrrolidin-1-yl)hexan-1-one and 2,4-dimethylisocathinone. Forensic Toxicol 2019; 37: 288-307. Westphal F, Girreser U, Angerer V, Auwärter V. Analytische Daten neuer 2-aminosubstituierter Methylendioxyvalerophenonderivate. Toxichem Krimtech, 2016 Jan 1; 83(1): 3–29. StructureCompoundR1R2R3R4CAS numberCathinoneHMeHH71031-15-7MethcathinoneHMeHMe5650-44-2EthcathinoneHMeHEt51553-17-4PropylcathinoneHMeHnPr52597-14-5BuphedroneHEtHMe408332-79-6NEBHEtHEt1354631-28-9N-methyl-N-ethylbuphedroneHEtMeEtPentedroneHnPrHMe879722-57-3N-EthylpentedroneHnPrHEt18268-16-1N-IsopropylpentedroneHnPrHiPrHexedroneHnBuHMeEthyl-HexedroneHnBuHEt18410-62-3N-Butyl-hexedroneHnBuHnBuN-Isobutylhexedrone (NDH)HnBuHi-BuIsohexedroneHiBuHMeN-EthylheptedroneHnPeHEtOctedroneHhexylHMeDimethylcathinoneHMeMeMe15351-09-4DiethylpropionHMeEtEt134-80-5N-methyl-N-ethylcathinoneHMeMeEt1157739-24-6Bupropion (3-CBP)3-ClMeHt-Bu34911-55-2Hydroxybupropion3-ClMeH2-Me-3-OH-propan-2-yl357399-43-0Mephedrone4-MeMeHMe1189805-46-62-MMC2-MeMeHMe2-MEC2-MeMeHEt2-EEC2-EtMeHEt3-MMC3-MeMeHMe1246816-62-53-MEC3-MeMeHEt3-EMC3-EtMeHMe3-EEC3-EtMeHEt4-EMC4-EtMeHMe1225622-14-94-EEC4-EtMeHEt4-MC4-MeMeHH31952-47-3Benzedrone4-MeMeHBn1225617-75-32'-MeO-Benzedrone4-MeMeH2-MeO-Bn4-MEC4-MeMeHEt1225617-18-44-MPC4-MeMeHnPrN,N-DMMC4-MeMeMeMeN,N-MEMC4-MeMeMeEtN,N-DEMC4-MeMeEtEt676316-90-84-MEAP4-MePrHEt746540-82-9EDMC4-EtMeMeMe2,4-DMMC2,4-dimethylMeHMe2,4-DMEC2,4-dimethylMeHEt3,4-DMMC3,4-dimethylMeHMe1082110-00-63,4-DMEC3,4-dimethylMeHEt2,4,5-TMMC2,4,5-trimethylMeHMe2,4,5-TMOMC2,4,5-trimethoxyMeHMe3,4,5-TMOMC3,4,5-trimethoxyMeHMeMethedrone4-MeOMeHMe530-54-1Dimethedrone4-MeOMeMeMe91564-39-5Ethedrone4-MeOMeHEt2-MOMC2-MeOMeHMe3-MOMC3-MeOMeHMe3-FC3-FMeHH4-FC4-FMeHH80096-51-12-FMC2-FMeHMe1186137-35-82-FEC2-FMeHEt3-FMC3-FMeHMe1049677-77-13-FEC3-FMeHEt2-CMC2-ClMeHMe2-BMC2-BrMeHMe2-IMC2-IMeHMe2-TFMAP2-CF3MeHMeClophedrone3-ClMeHMe1049677-59-93-CEC3-ClMeHEt3-BMC3-BrMeHMe3-IMC3-IMeHMe3-TFMAP3-CF3MeHMeFlephedrone4-FMeHMe447-40-54-FEC4-FMeHEt1225625-74-0Clephedrone4-ClMeHMe1225843-86-64-CEC4-ClMeHEt4-CiPC4-ClMeHiPr4-CBC4-ClMeHnBu4-CDMC4-ClMeMeMeBrephedrone4-BrMeHMe486459-03-44-BEC4-BrMeHEt4-IMC4-IMeHMe4-TFMAP4-CF3MeHMe4-EFMC4-(2-fluoroethyl)MeHMe4-MTMC4-SCH3MeHMe4-MSMC4-SO2CH3MeHMe4-PHMC4-phenylMeHMeMexedrone4-MemethoxymethylHMeFMMC3-F-4-MeMeHMeMFMC3-Me-4-FMeHMeMMOMC3-Me-4-MeOMeHMe3,4-DCMC3,4-dichloroMeHMe3,5-DCMC3,5-dichloroMeHMe3,5-DFMC3,5-difluoroMeHMe2,5-DMOMC2,5-dimethoxyMeHMeβk-2C-C2,5-dimethoxy-4-chloroHHH1538191-15-9βk-2C-B2,5-dimethoxy-4-bromoHHH807631-09-0βk-2C-I2,5-dimethoxy-4-iodoHHHβk-2C-D2,5-dimethoxy-4-methylHHH1368627-25-1βk-2C-E2,5-dimethoxy-4-ethylHHH1517021-02-1βk-2C-P2,5-dimethoxy-4-propylHHHβk-2C-iP2,5-dimethoxy-4-isopropylHHH1511033-62-7βk-DOB2,5-dimethoxy-4-bromoMeHHβk-MDOM2,5-dimethoxy-4-methylMeHMeβk-MDA3,4-methylenedioxyMeHH80535-73-5N-acetyl-βk-MDA3,4-methylenedioxyMeHacetyl2,3-MDMC2,3-methylenedioxyMeHMeMethylone3,4-methylenedioxyMeHMe186028-79-5Dimethylone3,4-methylenedioxyMeMeMeN-acetyl-methylone3,4-methylenedioxyMeacetylMeN-hydroxy-methylone3,4-methylenedioxyMehydroxyMeEthylone3,4-methylenedioxyMeHEt1112937-64-0Diethylone3,4-methylenedioxyMeEtEtN-acetyl-ethylone3,4-methylenedioxyMeacetylEtN-isopropyl-βk-MDA3,4-methylenedioxyMeHiPrMDPT3,4-methylenedioxyMeHt-BuBMDP3,4-methylenedioxyMeHBn3,4-EDMC3,4-ethylenedioxyMeHMeβk-IMP3,4-trimethyleneMeHMeβk-IBP3,4-trimethyleneEtHEtβk-IVP3,4-trimethylenenPrHEt3-Fluorobuphedrone3-FEtHMe4-Fluorobuphedrone4-FEtHMe4-Bromobuphedrone4-BrEtHMe4-MeMABP4-MeEtHMe1336911-98-84-Me-NEB4-MeEtHEt4-F-NEB4-FEtHEt4-Me-DMB4-MeEtMeMe3,4-DMEB3,4-dimethylEtHEt4-Methoxybuphedrone4-MeOEtHMeButylone3,4-methylenedioxyEtHMe802575-11-7Eutylone3,4-methylenedioxyEtHEt802855-66-9βk-PBDB3,4-methylenedioxyEtHnPrBn-4-MeMABP4-MeEtHBn1445751-39-2BMDB3,4-methylenedioxyEtHBn1445751-47-2βk-DMBDB3,4-methylenedioxyEtMeMe802286-83-5βk-MMDMA3,4-methylenedioxy-5-MeOMeHMeβk-MMDMA-22-MeO-3,4-methylenedioxyMeHMeβk-DMMDA2,5-diMeO-3,4-methylenedioxyMeHH5-Methylmethylone3,4-methylenedioxy-5-MeMeHMe1364933-83-45-Methylethylone3,4-methylenedioxy-5-MeMeHEt1364933-82-32-Methylbutylone2-Me-3,4-methylenedioxyEtHMe1364933-86-75-Methylbutylone3,4-methylenedioxy-5-MeEtHMe1354631-29-0Pentylone3,4-methylenedioxynPrHMe698963-77-8N-Ethylpentylone3,4-methylenedioxynPrHEt727641-67-0N-propylpentylone3,4-methylenedioxynPrHnPrN-butylpentylone3,4-methylenedioxynPrHnBuDipentylone3,4-methylenedioxynPrMeMeHexylone3,4-methylenedioxynBuHMeN-Ethylhexylone3,4-methylenedioxynBuHEtN-Ethylheptylone3,4-methylenedioxynPeHEt4-MEAP4-MenPrHEt746540-82-93,4-DMEP3,4-dimethylnPrHEt4-F-Pentedrone4-FnPrHMe4-Cl-Pentedrone4-ClnPrHMe4-Methylpentedrone4-MenPrHMe1373918-61-6DL-46623,4-dimethoxynPrHEt1674389-55-94-F-iPr-norpentedrone4-FnPrHiPr3-CBV3-ClnPrHtBu4-methylhexedrone4-MenBuHMeMEH4-MenBuHEt4-F-hexedrone4-FnBuHMe4-F-octedrone4-FhexylHMeα-phenylmephedrone4-MephenylHMeβk-EphenidineHphenylHEt22312-16-9"NRG-3"β-naphthyl instead of phenylMeHMeβk-Methiopropaminethiophen-2-yl instead of phenylMeHMe24065-17-6βk-5-MAPBbenzofuran-5-yl instead of phenylMeHMeβk-6-MAPBbenzofuran-6-yl instead of phenylMeHMeβk-5-ITindol-5-yl instead of phenylMeHHα-PhthalimidopropiophenoneHMephthalimido19437-20-8PPPOHMepiperidinylPPBOHEtpiperidinylFPPVO4-FnPrpiperidinylMDPV-azepane3,4-methylenedioxynPrazepaneCaccure 9074-SCH3α,α-di-Memorpholinylα-PPPHMepyrrolidinyl19134-50-0α-PBPHEtpyrrolidinyl13415-54-8α-PVP (O-2387)HnPrpyrrolidinyl14530-33-7α-PHPHnBupyrrolidinyl13415-86-6α-PHiPHiBupyrrolidinylα-PEP (α-PHPP)HnPepyrrolidinyl13415-83-3α-POPHhexylpyrrolidinylα-PNPHheptylpyrrolidinylDPPEHphenylpyrrolidinyl27590-61-0α-PcPePHcyclopentylpyrrolidinylα-PCYPHcyclohexylpyrrolidinyl1803168-11-72-MePPP2-MeMepyrrolidinyl3-MePPP3-MeMepyrrolidinyl1214940-01-84-MePPP4-MeMepyrrolidinyl1313393-58-6MOPPP4-MeOMepyrrolidinyl478243-09-33-F-PPP3-FMepyrrolidinyl1214939-99-7FPPP4-FMepyrrolidinyl28117-76-2Cl-PPP4-ClMepyrrolidinyl2,4-DMPPP2,4-dimethylMepyrrolidinyl3-MPBP3-MeEtpyrrolidinyl1373918-60-53-F-PBP3-FEtpyrrolidinyl1373918-59-2MPBP4-MeEtpyrrolidinyl732180-91-5FPBP4-FEtpyrrolidinyl1373918-67-2EPBP4-EtEtpyrrolidinylMOPBP4-MeOEtpyrrolidinylMMOPBP3-Me-4-MeOEtpyrrolidinylO-23843,4-dichloroEtpyrrolidinyl850352-65-7Pyrovalerone (O-2371)4-MenPrpyrrolidinyl3563-49-33-F-PVP3-FnPrpyrrolidinylFPVP4-FnPrpyrrolidinyl850352-31-74-Cl-PVP4-ClnPrpyrrolidinyl4-Br-PVP4-BrnPrpyrrolidinylMOPVP4-MeOnPrpyrrolidinyl5537-19-9DMOPVP3,4-dimethoxynPrpyrrolidinyl850442-84-1DMPVP3,4-dimethylnPrpyrrolidinylO-23903,4-dichloronPrpyrrolidinyl850352-61-3MFPVP3-methyl-4-fluoronPrpyrrolidinylMPHP4-MenBupyrrolidinyl34138-58-4FPHP4-FnBupyrrolidinyl4-Cl-PHP4-ClnBupyrrolidinylDMOPHP3,4-dimethoxynBupyrrolidinyl3F-PiHP3-FiBupyrrolidinyl4F-PiHP4-FiBupyrrolidinylO-23944-MeiBupyrrolidinyl850352-51-1MPEP4-Mepentylpyrrolidinyl4F-PV84-Fpentylpyrrolidinyl4-MeO-PV84-MeOpentylpyrrolidinyl4F-PV94-Fhexylpyrrolidinyl4-MeO-PV94-MeOhexylpyrrolidinylα-Phenylpyrovalerone4-MephenylpyrrolidinylMDPPP3,4-methylenedioxyMepyrrolidinyl783241-66-7MDMPP3,4-methylenedioxyα,α-di-MepyrrolidinylMDPBP3,4-methylenedioxyEtpyrrolidinyl784985-33-7MDPV3,4-methylenedioxynPrpyrrolidinyl687603-66-32,3-MDPV2,3-methylenedioxynPrpyrrolidinyl5-Me-MDPV3,4-methylenedioxy-5-MenPrpyrrolidinyl6-Me-MDPV2-Me-4,5-methylenedioxynPrpyrrolidinyl6-MeO-MDPV2-MeO-4,5-methylenedioxynPrpyrrolidinylBr-MeO-MDPV2,3-methylenedioxy-4-MeO-5-BrnPrpyrrolidinylMDPiVP3,4-methylenedioxyiPrpyrrolidinylMDPHP3,4-methylenedioxynBupyrrolidinyl776994-64-0MDPEP (MD-PV8)3,4-methylenedioxypentylpyrrolidinylMDPOP (MD-PV9)3,4-methylenedioxyhexylpyrrolidinyl5-PPDI3,4-trimethyleneEtpyrrolidinyl5-BPDI3,4-trimethylenenPrpyrrolidinyl5-HPDI3,4-trimethylenenBupyrrolidinylIPPV3,4-trimethylenephenylpyrrolidinylTH-PVP3,4-tetramethylenenPrpyrrolidinylTH-PHP3,4-tetramethylenenBupyrrolidinyl5-DBFPV2,3-dihydrobenzofuran-5-yl instead of PhnPrpyrrolidinyl1620807-94-43-BF-PVPbenzofuran-3-yl instead of PhnPrpyrrolidinylNaphyrone (O-2482)β-naphthyl instead of phenylnPrpyrrolidinyl850352-53-3α-Naphyroneα-naphthyl instead of phenylnPrpyrrolidinylα-PPTthiophen-2-yl instead of phenylMepyrrolidinylα-PBTthiophen-2-yl instead of phenylEtpyrrolidinylα-PVTthiophen-2-yl instead of phenylnPrpyrrolidinyl1400742-66-6
Status legale Il 2 aprile 2010, il Consiglio consultivo sull'abuso di droghe nel Regno Unito ha annunciato che sarebbe stato istituito un ampio divieto basato sulla struttura (e non quindi su una molecola precisa) di questa intera classe di composti, a seguito di un'ampia pubblicità sulle vendite sul mercato grigio e sull'uso ricreativo del mefedrone, un comune membro della famiglia. Questo divieto copre i composti con la suddetta struttura generale, con 28 composti specificatamente denominati.Advisory Council on the Misuse of Drugs (UK).
Le sostituzioni nella struttura generale per analoghi del nafirone soggetti al divieto possono essere descritte come segue: