Catinone sostituito

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Cathinone
Struttura chimica generale dei catinoni sostituiti, con R 1 -R 4 definiti nel testo

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.[1][2][3][4][5] Il catinone si trova naturalmente nella pianta khat le cui foglie vengono masticate come droga ricreativa.[6]

Elenco dei catinoni sostituiti[modifica | modifica wikitesto]

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:[7][8][9][10][11][12][13][14][15][16][17][18][19][20]

Structure Compound R1 R2 R3 R4 CAS number
Cathinone H Me H H 71031-15-7
Methcathinone H Me H Me 5650-44-2
Ethcathinone H Me H Et 51553-17-4
Propylcathinone H Me H nPr 52597-14-5
Buphedrone H Et H Me 408332-79-6
NEB H Et H Et 1354631-28-9
N-methyl-N-ethylbuphedrone H Et Me Et
Pentedrone H nPr H Me 879722-57-3
N-Ethylpentedrone H nPr H Et 18268-16-1
N-Isopropylpentedrone H nPr H iPr
Hexedrone H nBu H Me
Ethyl-Hexedrone H nBu H Et 18410-62-3
N-Butyl-hexedrone H nBu H nBu
N-Isobutylhexedrone (NDH) H nBu H i-Bu
Isohexedrone H iBu H Me
N-Ethylheptedrone H nPe H Et
Octedrone H hexyl H Me
Dimethylcathinone H Me Me Me 15351-09-4
Diethylpropion H Me Et Et 134-80-5
N-methyl-N-ethylcathinone H Me Me Et 1157739-24-6
Bupropion (3-CBP) 3-Cl Me H t-Bu 34911-55-2
Hydroxybupropion 3-Cl Me H 2-Me-3-OH-propan-2-yl 357399-43-0
Mephedrone 4-Me Me H Me 1189805-46-6
2-MMC 2-Me Me H Me
2-MEC 2-Me Me H Et
2-EEC 2-Et Me H Et
3-MMC 3-Me Me H Me 1246816-62-5
3-MEC 3-Me Me H Et
3-EMC 3-Et Me H Me
3-EEC 3-Et Me H Et
4-EMC 4-Et Me H Me 1225622-14-9
4-EEC 4-Et Me H Et
4-MC 4-Me Me H H 31952-47-3
Benzedrone 4-Me Me H Bn 1225617-75-3
2'-MeO-Benzedrone 4-Me Me H 2-MeO-Bn
4-MEC 4-Me Me H Et 1225617-18-4
4-MPC 4-Me Me H nPr
N,N-DMMC 4-Me Me Me Me
N,N-MEMC 4-Me Me Me Et
N,N-DEMC 4-Me Me Et Et 676316-90-8
4-MEAP 4-Me Pr H Et 746540-82-9
EDMC 4-Et Me Me Me
2,4-DMMC 2,4-dimethyl Me H Me
2,4-DMEC 2,4-dimethyl Me H Et
3,4-DMMC 3,4-dimethyl Me H Me 1082110-00-6
3,4-DMEC 3,4-dimethyl Me H Et
2,4,5-TMMC 2,4,5-trimethyl Me H Me
2,4,5-TMOMC 2,4,5-trimethoxy Me H Me
3,4,5-TMOMC 3,4,5-trimethoxy Me H Me
Methedrone 4-MeO Me H Me 530-54-1
Dimethedrone 4-MeO Me Me Me 91564-39-5
Ethedrone 4-MeO Me H Et
2-MOMC 2-MeO Me H Me
3-MOMC 3-MeO Me H Me
3-FC 3-F Me H H
4-FC 4-F Me H H 80096-51-1
2-FMC 2-F Me H Me 1186137-35-8
2-FEC 2-F Me H Et
3-FMC 3-F Me H Me 1049677-77-1
3-FEC 3-F Me H Et
2-CMC 2-Cl Me H Me
2-BMC 2-Br Me H Me
2-IMC 2-I Me H Me
2-TFMAP 2-CF3 Me H Me
Clophedrone 3-Cl Me H Me 1049677-59-9
3-CEC 3-Cl Me H Et
3-BMC 3-Br Me H Me
3-IMC 3-I Me H Me
3-TFMAP 3-CF3 Me H Me
Flephedrone 4-F Me H Me 447-40-5
4-FEC 4-F Me H Et 1225625-74-0
Clephedrone 4-Cl Me H Me 1225843-86-6
4-CEC 4-Cl Me H Et
4-CiPC 4-Cl Me H iPr
4-CBC 4-Cl Me H nBu
4-CDMC 4-Cl Me Me Me
Brephedrone 4-Br Me H Me 486459-03-4
4-BEC 4-Br Me H Et
4-IMC 4-I Me H Me
4-TFMAP 4-CF3 Me H Me
4-EFMC 4-(2-fluoroethyl) Me H Me
4-MTMC 4-SCH3 Me H Me
4-MSMC 4-SO2CH3 Me H Me
4-PHMC 4-phenyl Me H Me
Mexedrone 4-Me methoxymethyl H Me
FMMC 3-F-4-Me Me H Me
MFMC 3-Me-4-F Me H Me
MMOMC 3-Me-4-MeO Me H Me
3,4-DCMC 3,4-dichloro Me H Me
3,5-DCMC 3,5-dichloro Me H Me
3,5-DFMC 3,5-difluoro Me H Me
2,5-DMOMC 2,5-dimethoxy Me H Me
βk-2C-C 2,5-dimethoxy-4-chloro H H H 1538191-15-9
βk-2C-B 2,5-dimethoxy-4-bromo H H H 807631-09-0
βk-2C-I 2,5-dimethoxy-4-iodo H H H
βk-2C-D 2,5-dimethoxy-4-methyl H H H 1368627-25-1
βk-2C-E 2,5-dimethoxy-4-ethyl H H H 1517021-02-1
βk-2C-P 2,5-dimethoxy-4-propyl H H H
βk-2C-iP 2,5-dimethoxy-4-isopropyl H H H 1511033-62-7
βk-DOB 2,5-dimethoxy-4-bromo Me H H
βk-MDOM 2,5-dimethoxy-4-methyl Me H Me
βk-MDA 3,4-methylenedioxy Me H H 80535-73-5
N-acetyl-βk-MDA 3,4-methylenedioxy Me H acetyl
2,3-MDMC 2,3-methylenedioxy Me H Me
Methylone 3,4-methylenedioxy Me H Me 186028-79-5
Dimethylone 3,4-methylenedioxy Me Me Me
N-acetyl-methylone 3,4-methylenedioxy Me acetyl Me
N-hydroxy-methylone 3,4-methylenedioxy Me hydroxy Me
Ethylone 3,4-methylenedioxy Me H Et 1112937-64-0
Diethylone 3,4-methylenedioxy Me Et Et
N-acetyl-ethylone 3,4-methylenedioxy Me acetyl Et
N-isopropyl-βk-MDA 3,4-methylenedioxy Me H iPr
MDPT 3,4-methylenedioxy Me H t-Bu
BMDP 3,4-methylenedioxy Me H Bn
3,4-EDMC 3,4-ethylenedioxy Me H Me
βk-IMP 3,4-trimethylene Me H Me
βk-IBP 3,4-trimethylene Et H Et
βk-IVP 3,4-trimethylene nPr H Et
3-Fluorobuphedrone 3-F Et H Me
4-Fluorobuphedrone 4-F Et H Me
4-Bromobuphedrone 4-Br Et H Me
4-MeMABP 4-Me Et H Me 1336911-98-8
4-Me-NEB 4-Me Et H Et
4-F-NEB 4-F Et H Et
4-Me-DMB 4-Me Et Me Me
3,4-DMEB 3,4-dimethyl Et H Et
4-Methoxybuphedrone 4-MeO Et H Me
Butylone 3,4-methylenedioxy Et H Me 802575-11-7
Eutylone 3,4-methylenedioxy Et H Et 802855-66-9
βk-PBDB 3,4-methylenedioxy Et H nPr
Bn-4-MeMABP 4-Me Et H Bn 1445751-39-2
BMDB 3,4-methylenedioxy Et H Bn 1445751-47-2
βk-DMBDB 3,4-methylenedioxy Et Me Me 802286-83-5
βk-MMDMA 3,4-methylenedioxy-5-MeO Me H Me
βk-MMDMA-2 2-MeO-3,4-methylenedioxy Me H Me
βk-DMMDA 2,5-diMeO-3,4-methylenedioxy Me H H
5-Methylmethylone 3,4-methylenedioxy-5-Me Me H Me 1364933-83-4
5-Methylethylone 3,4-methylenedioxy-5-Me Me H Et 1364933-82-3
2-Methylbutylone 2-Me-3,4-methylenedioxy Et H Me 1364933-86-7
5-Methylbutylone 3,4-methylenedioxy-5-Me Et H Me 1354631-29-0
Pentylone 3,4-methylenedioxy nPr H Me 698963-77-8
N-Ethylpentylone 3,4-methylenedioxy nPr H Et 727641-67-0
N-propylpentylone 3,4-methylenedioxy nPr H nPr
N-butylpentylone 3,4-methylenedioxy nPr H nBu
Dipentylone 3,4-methylenedioxy nPr Me Me
Hexylone 3,4-methylenedioxy nBu H Me
N-Ethylhexylone 3,4-methylenedioxy nBu H Et
N-Ethylheptylone 3,4-methylenedioxy nPe H Et
4-MEAP 4-Me nPr H Et 746540-82-9
3,4-DMEP 3,4-dimethyl nPr H Et
4-F-Pentedrone 4-F nPr H Me
4-Cl-Pentedrone 4-Cl nPr H Me
4-Methylpentedrone 4-Me nPr H Me 1373918-61-6
DL-4662 3,4-dimethoxy nPr H Et 1674389-55-9
4-F-iPr-norpentedrone 4-F nPr H iPr
3-CBV 3-Cl nPr H tBu
4-methylhexedrone 4-Me nBu H Me
MEH 4-Me nBu H Et
4-F-hexedrone 4-F nBu H Me
4-F-octedrone 4-F hexyl H Me
α-phenylmephedrone 4-Me phenyl H Me
βk-Ephenidine H phenyl H Et 22312-16-9
"NRG-3" β-naphthyl instead of phenyl Me H Me
βk-Methiopropamine thiophen-2-yl instead of phenyl Me H Me 24065-17-6
βk-5-MAPB benzofuran-5-yl instead of phenyl Me H Me
βk-6-MAPB benzofuran-6-yl instead of phenyl Me H Me
βk-5-IT indol-5-yl instead of phenyl Me H H
α-Phthalimidopropiophenone H Me phthalimido 19437-20-8
PPPO H Me piperidinyl
PPBO H Et piperidinyl
FPPVO 4-F nPr piperidinyl
MDPV-azepane 3,4-methylenedioxy nPr azepane
Caccure 907 4-SCH3 α,α-di-Me morpholinyl
α-PPP H Me pyrrolidinyl 19134-50-0
α-PBP H Et pyrrolidinyl 13415-54-8
α-PVP (O-2387) H nPr pyrrolidinyl 14530-33-7
α-PHP H nBu pyrrolidinyl 13415-86-6
α-PHiP H iBu pyrrolidinyl
α-PEP (α-PHPP) H nPe pyrrolidinyl 13415-83-3
α-POP H hexyl pyrrolidinyl
α-PNP H heptyl pyrrolidinyl
DPPE H phenyl pyrrolidinyl 27590-61-0
α-PcPeP H cyclopentyl pyrrolidinyl
α-PCYP H cyclohexyl pyrrolidinyl 1803168-11-7
2-MePPP 2-Me Me pyrrolidinyl
3-MePPP 3-Me Me pyrrolidinyl 1214940-01-8
4-MePPP 4-Me Me pyrrolidinyl 1313393-58-6
MOPPP 4-MeO Me pyrrolidinyl 478243-09-3
3-F-PPP 3-F Me pyrrolidinyl 1214939-99-7
FPPP 4-F Me pyrrolidinyl 28117-76-2
Cl-PPP 4-Cl Me pyrrolidinyl
2,4-DMPPP 2,4-dimethyl Me pyrrolidinyl
3-MPBP 3-Me Et pyrrolidinyl 1373918-60-5
3-F-PBP 3-F Et pyrrolidinyl 1373918-59-2
MPBP 4-Me Et pyrrolidinyl 732180-91-5
FPBP 4-F Et pyrrolidinyl 1373918-67-2
EPBP 4-Et Et pyrrolidinyl
MOPBP 4-MeO Et pyrrolidinyl
MMOPBP 3-Me-4-MeO Et pyrrolidinyl
O-2384 3,4-dichloro Et pyrrolidinyl 850352-65-7
Pyrovalerone (O-2371) 4-Me nPr pyrrolidinyl 3563-49-3
3-F-PVP 3-F nPr pyrrolidinyl
FPVP 4-F nPr pyrrolidinyl 850352-31-7
4-Cl-PVP 4-Cl nPr pyrrolidinyl
4-Br-PVP 4-Br nPr pyrrolidinyl
MOPVP 4-MeO nPr pyrrolidinyl 5537-19-9
DMOPVP 3,4-dimethoxy nPr pyrrolidinyl 850442-84-1
DMPVP 3,4-dimethyl nPr pyrrolidinyl
O-2390 3,4-dichloro nPr pyrrolidinyl 850352-61-3
MFPVP 3-methyl-4-fluoro nPr pyrrolidinyl
MPHP 4-Me nBu pyrrolidinyl 34138-58-4
FPHP 4-F nBu pyrrolidinyl
4-Cl-PHP 4-Cl nBu pyrrolidinyl
DMOPHP 3,4-dimethoxy nBu pyrrolidinyl
3F-PiHP 3-F iBu pyrrolidinyl
4F-PiHP 4-F iBu pyrrolidinyl
O-2394 4-Me iBu pyrrolidinyl 850352-51-1
MPEP 4-Me pentyl pyrrolidinyl
4F-PV8 4-F pentyl pyrrolidinyl
4-MeO-PV8 4-MeO pentyl pyrrolidinyl
4F-PV9 4-F hexyl pyrrolidinyl
4-MeO-PV9 4-MeO hexyl pyrrolidinyl
α-Phenylpyrovalerone 4-Me phenyl pyrrolidinyl
MDPPP 3,4-methylenedioxy Me pyrrolidinyl 783241-66-7
MDMPP 3,4-methylenedioxy α,α-di-Me pyrrolidinyl
MDPBP 3,4-methylenedioxy Et pyrrolidinyl 784985-33-7
MDPV 3,4-methylenedioxy nPr pyrrolidinyl 687603-66-3
2,3-MDPV 2,3-methylenedioxy nPr pyrrolidinyl
5-Me-MDPV 3,4-methylenedioxy-5-Me nPr pyrrolidinyl
6-Me-MDPV 2-Me-4,5-methylenedioxy nPr pyrrolidinyl
6-MeO-MDPV 2-MeO-4,5-methylenedioxy nPr pyrrolidinyl
Br-MeO-MDPV 2,3-methylenedioxy-4-MeO-5-Br nPr pyrrolidinyl
MDPiVP 3,4-methylenedioxy iPr pyrrolidinyl
MDPHP 3,4-methylenedioxy nBu pyrrolidinyl 776994-64-0
MDPEP (MD-PV8) 3,4-methylenedioxy pentyl pyrrolidinyl
MDPOP (MD-PV9) 3,4-methylenedioxy hexyl pyrrolidinyl
5-PPDI 3,4-trimethylene Et pyrrolidinyl
5-BPDI 3,4-trimethylene nPr pyrrolidinyl
5-HPDI 3,4-trimethylene nBu pyrrolidinyl
IPPV 3,4-trimethylene phenyl pyrrolidinyl
TH-PVP 3,4-tetramethylene nPr pyrrolidinyl
TH-PHP 3,4-tetramethylene nBu pyrrolidinyl
5-DBFPV 2,3-dihydrobenzofuran-5-yl instead of Ph nPr pyrrolidinyl 1620807-94-4
3-BF-PVP benzofuran-3-yl instead of Ph nPr pyrrolidinyl
Naphyrone (O-2482) β-naphthyl instead of phenyl nPr pyrrolidinyl 850352-53-3
α-Naphyrone α-naphthyl instead of phenyl nPr pyrrolidinyl
α-PPT thiophen-2-yl instead of phenyl Me pyrrolidinyl
α-PBT thiophen-2-yl instead of phenyl Et pyrrolidinyl
α-PVT thiophen-2-yl instead of phenyl nPr pyrrolidinyl 1400742-66-6

Status legale[modifica | modifica wikitesto]

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.[21]

Struttura chimica generale dei nafironi sostituiti, con R 1 -R 3 definito nel testo

Le sostituzioni nella struttura generale per analoghi del nafirone soggetti al divieto possono essere descritte come segue:

  • Cyc = qualsiasi sistema ad anello monociclico o fuso-policiclico (che non sia un anello fenilico o un sistema ad anello alchilendiossifenile), compresi gli analoghi in cui il sistema ad anello è sostituito in qualsiasi misura con sostituenti alchilici, alcossilici, aloalchilici o alogenuri, anche se non ulteriormente sostituiti in il sistema ad anello da uno o più altri sostituenti univalenti
  • R 1 = idrogeno o qualsiasi gruppo alchile
  • R 2 = idrogeno, qualsiasi gruppo alchilico o incorporazione in una struttura ciclica
  • R 3 = idrogeno, qualsiasi gruppo alchilico o incorporazione in una struttura ciclica

Tuttavia, sono continuati ad apparire altri nuovi derivati, con il Regno Unito che ha segnalato più nuovi derivati del catinone rilevati nel 2010 rispetto a qualsiasi altro paese in Europa, con la maggior parte di essi identificati per la prima volta dopo l'entrata in vigore del divieto generico e quindi già illegali nonostante non siano mai stati segnalato in precedenza.[22]

Negli Stati Uniti, i catinoni sostituiti sono gli ingredienti psicoattivi dei "sali da bagno" che a partire dal luglio 2011 erano stati banditi da almeno 28 stati, ma non dal governo federale.[23]

Note[modifica | modifica wikitesto]

  1. ^ 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. PMID 16480278 DOI: 10.1021/jm050797a
  2. ^ 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. PMID 24966713 DOI: 10.2147/SAR.S37257
  3. ^ 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. PMID 29714473 DOI: 10.1021/acschemneuro.8b00147
  4. ^ 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. PMID 28895757 DOI: 10.1080/15563650.2017.1370097
  5. ^ 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. PMID 29367861 DOI: 10.1007/s11419-017-0385-6
  6. ^ 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. PMID 21698275. accesso 2011-07-17.
  7. ^ Europol 2008 Annual Report on the implementation of Council Decision 2005/387/JHA
  8. ^ Europol 2009 Annual Report on the implementation of Council Decision 2005/387/JHA
  9. ^ Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA
  10. ^ Europol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA
  11. ^ Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA
  12. ^ Europol 2013 Annual Report on the implementation of Council Decision 2005/387/JHA
  13. ^ Europol 2014 Annual Report on the implementation of Council Decision 2005/387/JHA
  14. ^ Europol 2015 Annual Report on the implementation of Council Decision 2005/387/JHA
  15. ^ Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA
  16. ^ Europol 2017 Annual Report on the implementation of Council Decision 2005/387/JHA
  17. ^ 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. PMID 15228152
  18. ^ 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. PMID 22088945 DOI: 10.1016/j.forsciint.2011.10.042
  19. ^ 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. DOI: 10.1007/s11419-018-00463-w
  20. ^ Westphal F, Girreser U, Angerer V, Auwärter V. Analytische Daten neuer 2-aminosubstituierter Methylendioxyvalerophenonderivate. Toxichem Krimtech, 2016 Jan 1; 83(1): 3–29.
  21. ^ Advisory Council on the Misuse of Drugs (UK). Consideration of the cathinones. 31 March 2010., su homeoffice.gov.uk. URL consultato il 17 luglio 2011. (archiviato dall'url originale il 22 settembre 2011).
  22. ^ European Monitoring Centre on Drugs and Drug Addiction. EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA. Archiviato il 14 marzo 2012 in Internet Archive. accesso 2011-07-17.
  23. ^ Goodnough A, Zezima K. An Alarming New Stimulant, Legal in Many States. New York Times 2011 July 16. accesso 2011-07-17.

Altri progetti[modifica | modifica wikitesto]

  Portale Chimica: il portale della scienza della composizione, delle proprietà e delle trasformazioni della materia
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