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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]
I derivati possono essere prodotti mediante sostituzioni in quattro posizioni della molecola del catinone:
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 | ||
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]
Le sostituzioni nella struttura generale per analoghi del nafirone soggetti al divieto possono essere descritte come segue:
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 catinoni sintetici che a partire dal luglio 2011 erano stati banditi da almeno 28 stati, ma non dal governo federale.[23]
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