Chemistry:Substituted cathinone

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Short description: Class of chemical compounds
Cathinone
General chemical structure of substituted cathinones, with R1-R4 defined in text

Substituted cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions.[1][2][3][4][5] Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug.[6]

List of substituted cathinones

The derivatives may be produced by substitutions at four locations of the cathinone molecule:

  • R1 = hydrogen, or any combination of one or more alkyl, alkoxy, alkylenedioxy, haloalkyl or halide substituents
  • R2 = hydrogen or any alkyl group
  • R3 = hydrogen, any alkyl group, or incorporation in a cyclic structure
  • R4 = hydrogen, any alkyl group, or incorporation in a cyclic structure

The following table displays notable derivatives that have been reported:[7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28]


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
Error creating thumbnail: Unable to save thumbnail to destination N-Ethylbuphedrone (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 18268-14-9
Hexedrone H nBu H Me 2169446-41-5
N-Ethylhexedrone H nBu H Et 18410-62-3
N-Butylhexedrone H nBu H nBu 18296-66-7
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-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 1246911-71-6
2-MEC 2-Me Me H Et 1439439-84-5
2-EMC 2-Et Me H Me
2-EEC 2-Et Me H Et 2446466-59-5
3-MMC 3-Me Me H Me 1246816-62-5
3-MEC 3-Me Me H Et 1439439-83-4
3-MPC 3-Me Me H nPr
3-EMC 3-Et Me H Me
3-EEC 3-Et Me H Et 2446466-61-9
4-EMC 4-Et Me H Me 1225622-14-9
4-EEC 4-Et Me H Et 2446466-62-0
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
2,N-Dimethylbenzedrone 2-Me Me Me Bn
3,N-Dimethylbenzedrone 3-Me Me Me Bn
4,N-Dimethylbenzedrone 4-Me Me Me 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 1448845-14-4
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
2,3-DMMC 2,3-dimethyl Me H Me
2,3-DMEC 2,3-dimethyl Me H Et
2,4-DMMC 2,4-dimethyl Me H Me 1225623-63-1
2,4-DMEC 2,4-dimethyl Me H Et 1225913-88-1
2,5-DMMC 2,5-dimethyl Me H Me
2,5-DMEC 2,5-dimethyl Me H Et
2,6-DMMC 2,6-dimethyl Me H Me
2,6-DMEC 2,6-dimethyl Me H Et
3,4-DMMC 3,4-dimethyl Me H Me 1082110-00-6
Error creating thumbnail: 3,4-DMEC 3,4-dimethyl Me H Et 1225811-81-3
File:3,5-DMEC structure.png 3,5-DMEC 3,5-dimethyl Me H Et
File:245-TMMC structure.png 2,4,5-TMMC 2,4,5-trimethyl Me H Me 1368603-85-3
File:245-TMOMC structure.png 2,4,5-TMOMC 2,4,5-trimethoxy Me H Me
File:345-TMOMC structure.png 3,4,5-TMOMC 3,4,5-trimethoxy Me H Me
Methedrone 4-MeO Me H Me 530-54-1
File:Dimethedrone structure.png Dimethedrone 4-MeO Me Me Me 91564-39-5
File:Ethedrone structure.png Ethedrone 4-MeO Me H Et
File:2-MOMC structure.png 2-MOMC 2-MeO Me H Me
File:3-MOMC structure.png 3-MOMC 3-MeO Me H Me 1435933-70-2
File:3-fluorocathinone structure.png 3-FC 3-F Me H H 1082949-91-4
File:4-fluorocathinone structure.png 4-FC 4-F Me H H 80096-51-1
File:2-FMC structure.png 2-FMC 2-F Me H Me 1186137-35-8
File:2-FEC structure.png 2-FEC 2-F Me H Et
3-FMC 3-F Me H Me 1049677-77-1
File:3-FEC structure.png 3-FEC 3-F Me H Et
File:2-CMC structure.png 2-CMC 2-Cl Me H Me
File:2-BMC structure.png 2-BMC 2-Br Me H Me
File:2-IMC structure.png 2-IMC 2-I Me H Me
File:2-TFMMC structure.png 2-TFMAP 2-CF3 Me H Me
Clophedrone 3-Cl Me H Me 1049677-59-9
File:3-CEC structure.png 3-CEC 3-Cl Me H Et 2150476-60-9
File:3-BMC structure.png 3-BMC 3-Br Me H Me 676487-42-6
File:3-IMC structure.png 3-IMC 3-I Me H Me
File:3-TFMMC structure.png 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
File:2Cl-NEC structure.png 2-CEC 2-Cl Me H Et
File:4-CEC structure.png 4-CEC 4-Cl Me H Et 14919-85-8
File:2Cl-NiPC structure.png 2-CiPC 2-Cl Me H iPr
File:3Cl-NiPC structure.png 3-CiPC 3-Cl Me H iPr
File:4-CiPC structure.png 4-CiPC 4-Cl Me H iPr
File:4-CBC structure.png 4-CBC 4-Cl Me H nBu 1225621-71-5
File:2Cl-DMC structure.png 2-CDMC 2-Cl Me Me Me
File:3Cl-DMC structure.png 3-CDMC 3-Cl Me Me Me
File:4-CDMC structure.png 4-CDMC 4-Cl Me Me Me 1157667-29-2
Brephedrone 4-Br Me H Me 486459-03-4
File:4-BEC structure.png 4-BEC 4-Br Me H Et 135333-26-5
File:4-IMC structure.png 4-IMC 4-I Me H Me
File:4-TFMMC structure.png 4-TFMAP 4-CF3 Me H Me
File:4-EFMC structure.png 4-EFMC 4-(2-fluoroethyl) Me H Me
File:4-MTMC structure.png 4-MTMC 4-SCH3 Me H Me
File:4-MSMC structure.png 4-MSMC 4-SO2CH3 Me H Me
File:4-PHMC structure.png 4-PHMC 4-phenyl Me H Me
Mexedrone 4-Me methoxymethyl H Me
File:3,4-FMMC structure.png FMMC 3-F-4-Me Me H Me 1696642-00-8
File:3,4-MFMC structure.png MFMC 3-Me-4-F Me H Me 1368943-21-8
File:4-Cl-3-MMC structure.png 4-Cl-3-MMC 3-Me-4-Cl Me H Me
File:3,4-MMOMC structure.png MMOMC 3-Me-4-MeO Me H Me
File:3,4-DCMC structure.png 3,4-DCMC 3,4-dichloro Me H Me 802281-39-6
File:3,4-DCEC structure.png 3,4-DCEC 3,4-dichloro Me H Et 1225618-63-2
File:3,5-DCMC structure.png 3,5-DCMC 3,5-dichloro Me H Me
3,5-DFMC 3,5-difluoro Me H Me 1430343-55-7
File:2,5-DMOMC structure.png 2,5-DMOMC 2,5-dimethoxy Me H Me
File:Bk2CC structure.png 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
File:Bk2CI structure.png βk-2C-I 2,5-dimethoxy-4-iodo H H H
File:Bk2CD structure.png βk-2C-D 2,5-dimethoxy-4-methyl H H H 1368627-25-1
File:Bk2CE structure.png βk-2C-E 2,5-dimethoxy-4-ethyl H H H 1517021-02-1
File:Bk2CP structure.png βk-2C-P 2,5-dimethoxy-4-propyl H H H
File:Bk2CiP structure.png βk-2C-iP 2,5-dimethoxy-4-isopropyl H H H 1511033-62-7
File:BkDOB structure.png βk-DOB 2,5-dimethoxy-4-bromo Me H H
File:BkMDOM structure.png βk-MDOM 2,5-dimethoxy-4-methyl Me H Me
Error creating thumbnail: Unable to save thumbnail to destination βk-MDA 3,4-methylenedioxy Me H H 80535-73-5
File:BkMDAc structure.png N-Acetyl-βk-MDA 3,4-methylenedioxy Me H acetyl
File:2,3-MDMC structure.png 2,3-MDMC 2,3-methylenedioxy Me H Me 1427205-87-5
Methylone 3,4-methylenedioxy Me H Me 186028-79-5
Dimethylone 3,4-methylenedioxy Me Me Me 109367-07-9
File:NAc-Methylone structure.png N-Acetylmethylone 3,4-methylenedioxy Me acetyl Me
File:NOH-Methylone structure.png N-Hydroxymethylone 3,4-methylenedioxy Me hydroxy Me
Error creating thumbnail: Unable to save thumbnail to destination Ethylone 3,4-methylenedioxy Me H Et 1112937-64-0
File:Diethylone structure.png Diethylone 3,4-methylenedioxy Me Et Et
File:NAc-Ethylone structure.png N-Acetylethylone 3,4-methylenedioxy Me acetyl Et
File:BkMDiP structure.png N-Isopropyl-βk-MDA 3,4-methylenedioxy Me H iPr
File:BkMDtB structure.png MDPT 3,4-methylenedioxy Me H t-Bu 186028-84-2
Benzylone (BMDP) 3,4-methylenedioxy Me H Bn 1823274-68-5
File:N-Cyclohexylmethylone structure.png N-Cyclohexylmethylone 3,4-methylenedioxy Me H cyclohexyl
File:3,4-EDMC structure.png 3,4-EDMC 3,4-ethylenedioxy Me H Me 30253-44-2
File:BkIMP structure.png βk-IMP 3,4-trimethylene Me H Me 100608-69-3
File:BkIEB structure.png βk-IBP 3,4-trimethylene Et H Et
File:BkIEV structure.png βk-IVP 3,4-trimethylene nPr H Et
File:3-fluorobuphedrone structure.png 3-Fluorobuphedrone 3-F Et H Me
File:4-fluorobuphedrone structure.png 4-Fluorobuphedrone 4-F Et H Me 1368599-12-5
File:4-bromobuphedrone structure.png 4-Bromobuphedrone 4-Br Et H Me
Error creating thumbnail: 3-Methylbuphedrone 3-Me Et H Me 1797911-07-9
4-Me-MABP 4-Me Et H Me 1336911-98-8
File:4-Me-NEB structure.png 4-Me-NEB 4-Me Et H Et 18268-19-4
File:2F-NEB structure.png 2-F-NEB 2-F Et H Et
3F-NEB 3-F Et H Et
File:4-F-NEB structure.png 4-F-NEB 4-F Et H Et
File:4-Me-DMB structure.png 4-Me-DMB 4-Me Et Me Me
File:3,4-DMEB structure.png 3,4-DMEB 3,4-dimethyl Et H Et
File:4-methoxybuphedrone structure.png 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
File:BkPBDB structure.png βk-PBDB 3,4-methylenedioxy Et H nPr
File:Bn-4-Me-MABP structure.png Bn-4-MeMABP 4-Me Et H Bn 1445751-39-2
File:BMDB structure.png BMDB 3,4-methylenedioxy Et H Bn 1445751-47-2
File:N-Cyclohexylbutylone structure.png N-Cyclohexylbutylone 3,4-methylenedioxy Et H cyclohexyl
βk-DMBDB 3,4-methylenedioxy Et Me Me 802286-83-5
βk-MMDMA 3,4-methylenedioxy-5-MeO Me H Me 2230716-98-8
File:2-methoxymethylone structure.png βk-MMDMA-2 2-MeO-3,4-methylenedioxy Me H Me
File:BkDMMDA structure.png βk-DMMDA 2,5-diMeO-3,4-methylenedioxy Me H H
File:5-methylmethylone structure.png 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
File:2-methylbutylone structure.png 2-Methylbutylone 2-Me-3,4-methylenedioxy Et H Me 1364933-86-7
File:5-methylbutylone structure.png 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
File:N-propylpentylone structure.png N-propylpentylone 3,4-methylenedioxy nPr H nPr
File:N-butylpentylone structure.png N-butylpentylone 3,4-methylenedioxy nPr H nBu
File:2,3-Dipentylone structure.png 2,3-Dipentylone 2,3-methylenedioxy nPr Me Me
Dipentylone 3,4-methylenedioxy nPr Me Me 17763-13-2
File:NN-diethyl-pentylone structure.png N,N-Diethylnorpentylone 3,4-methylenedioxy nPr Et Et
File:Hexylone structure.png Hexylone 3,4-methylenedioxy nBu H Me
Isohexylone 3,4-methylenedioxy iBu H Me 1157947-89-1
File:Isoheptylone structure.png Isoheptylone 3,4-methylenedioxy iPe H Me
N-Ethylhexylone 3,4-methylenedioxy nBu H Et 27912-41-0
N-Ethylheptylone 3,4-methylenedioxy nPe H Et
4-MEAP 4-Me nPr H Et 746540-82-9
File:3,4-DMEP structure.png 3,4-DMEP 3,4-dimethyl nPr H Et
File:2F-Pentedrone structure.png 2-F-Pentedrone 2-F nPr H Me
File:3F-Pentedrone structure.png 3-F-Pentedrone 3-F nPr H Me
File:4-fluoropentedrone structure.png 4-F-Pentedrone 4-F nPr H Me
File:4-chloropentedrone structure.png 4-Cl-Pentedrone 4-Cl nPr H Me 2167949-43-9
4-Methylpentedrone 4-Me nPr H Me 1373918-61-6
File:DL-4662 structure.png DL-4662 3,4-dimethoxy nPr H Et 1674389-55-9
File:4F-NiP-pentedrone structure.png 4-F-iPr-norpentedrone 4-F nPr H iPr
File:4Cl-NtB-pentedrone structure.png 3-CBV 3-Cl nPr H tBu
File:4-methylhexedrone structure.png 4-methylhexedrone 4-Me nBu H Me
File:4-methyl-N-ethylhexedrone structure.png MEH 4-Me nBu H Et
Error creating thumbnail: Unable to save thumbnail to destination 3F-NEH 3-F nBu H Et
File:4-fluorohexedrone structure.png 4-F-hexedrone 4-F nBu H Me
File:4-fluorooctedrone structure.png 4-F-octedrone 4-F hexyl H Me
File:Alpha-phenylmephedrone structure.png α-phenylmephedrone 4-Me phenyl H Me
βk-Ephenidine H phenyl H Et 22312-16-9
BMAPN β-naphthyl instead of phenyl Me H Me
βk-Methiopropamine thiophen-2-yl instead of phenyl Me H Me 24065-17-6
Error creating thumbnail: Unable to save thumbnail to destination 5-Cl-bk-MPA 5-chlorothiophen-2-yl instead of phenyl Me H Me
File:Bk-5-MAPB structure.png βk-5-MAPB benzofuran-5-yl instead of phenyl Me H Me
File:Bk-6-MAPB structure.png βk-6-MAPB benzofuran-6-yl instead of phenyl Me H Me
File:Bk-5-IT structure.png βk-5-IT indol-5-yl instead of phenyl Me H H 1369231-36-6
File:BK-5F-NM-AMT structure.png βk-5F-NM-AMT[29] 5-fluoroindol-3-yl instead of phenyl Me H Me
Error creating thumbnail: Unable to save thumbnail to destination α-Phthalimidopropiophenone H Me phthalimido 19437-20-8
File:PPPO structure.png PPPO H Me piperidinyl
File:PPBO structure.png PPBO H Et piperidinyl 92728-82-0
File:FPPVO structure.png FPPVO 4-F nPr piperidinyl
File:MDPV-azepane structure.png MDPV-azepane 3,4-methylenedioxy nPr azepane
File:Caccure907 structure.png 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
File:Alpha-POP structure.png α-POP H hexyl pyrrolidinyl
File:Alpha-PNP structure.png α-PNP H heptyl pyrrolidinyl
File:Diphenylpyrrolidinylethanone structure.png DPPE (A-D2PV) H phenyl pyrrolidinyl 27590-61-0
File:Alpha-PcPeP structure.png α-PcPeP H cyclopentyl pyrrolidinyl
α-PCYP H cyclohexyl pyrrolidinyl 1803168-11-7
File:2-Me-PPP structure.png 2-MePPP 2-Me Me pyrrolidinyl 2092429-83-7
File:3-Me-PPP structure.png 3-MePPP 3-Me Me pyrrolidinyl 1214940-01-8
4-MePPP 4-Me Me pyrrolidinyl 1313393-58-6
File:3MeO-PPP structure.png 3-MeO-PPP 3-MeO Me pyrrolidinyl
MOPPP 4-MeO Me pyrrolidinyl 478243-09-3
File:3-F-PPP structure.png 3-F-PPP 3-F Me pyrrolidinyl 1214939-99-7
File:4-F-PPP structure.png FPPP 4-F Me pyrrolidinyl 28117-76-2
File:4-Cl-PPP structure.png Cl-PPP 4-Cl Me pyrrolidinyl 93307-24-5
File:3-Br-PPP structure.png 3-Br-PPP 3-Br Me pyrrolidinyl
File:4Br-PPP structure.png Br-PPP 4-Br Me pyrrolidinyl
File:2,3-DMPPP structure.png 2,3-DMPPP 2,3-dimethyl Me pyrrolidinyl
File:2,4-DMPPP structure.png 2,4-DMPPP 2,4-dimethyl Me pyrrolidinyl
File:3,4-DMPPP structure.png 3,4-DMPPP 3,4-dimethyl Me pyrrolidinyl
File:3-Me-PBP structure.png 3-MPBP 3-Me Et pyrrolidinyl 1373918-60-5
File:3-F-PBP structure.png 3-F-PBP 3-F Et pyrrolidinyl 1373918-59-2
MPBP 4-Me Et pyrrolidinyl 732180-91-5
File:4-F-PBP structure.png FPBP 4-F Et pyrrolidinyl 1373918-67-2
File:4-Et-PBP structure.png EPBP 4-Et Et pyrrolidinyl
File:4-MeO-PBP structure.png MOPBP 4-MeO Et pyrrolidinyl
File:MMOPBP structure.png MMOPBP 3-Me-4-MeO Et pyrrolidinyl
File:O-2384 structure.png O-2384 3,4-dichloro Et pyrrolidinyl 850352-65-7
2-Me-PVP 2-Me nPr pyrrolidinyl
Pyrovalerone (O-2371) 4-Me nPr pyrrolidinyl 3563-49-3
4-Et-PVP 4-Et nPr pyrrolidinyl
File:3-F-PVP structure.png 3F-PVP 3-F nPr pyrrolidinyl
FPVP 4-F nPr pyrrolidinyl 850352-31-7
File:2Cl-PVP structure.png 2-Cl-PVP 2-Cl nPr pyrrolidinyl
File:3Cl-PVP structure.png 3-Cl-PVP 3-Cl nPr pyrrolidinyl
File:4-Cl-PVP structure.png 4-Cl-PVP 4-Cl nPr pyrrolidinyl 5537-17-7
File:3-Br-PVP structure.png 3-Br-PVP 3-Br nPr pyrrolidinyl
File:4-Br-PVP structure.png 4-Br-PVP 4-Br nPr pyrrolidinyl
MOPVP 4-MeO nPr pyrrolidinyl 5537-19-9
DMOPVP 3,4-dimethoxy nPr pyrrolidinyl 850442-84-1
File:3,4-DMPVP structure.png 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
3F-PHP 3-F nBu pyrrolidinyl
4F-PHP 4-F nBu pyrrolidinyl 2230706-09-7
4-Cl-PHP 4-Cl nBu pyrrolidinyl 2748592-29-0
File:DMOPHP structure.png DMOPHP 3,4-dimethoxy nBu pyrrolidinyl
File:MFPHP structure.png MFPHP 3-Me-4-F nBu pyrrolidinyl
Error creating thumbnail: Unable to save thumbnail to destination 3F-PiHP 3-F iBu pyrrolidinyl
File:4-F-PiHP structure.png 4F-PiHP 4-F iBu pyrrolidinyl
File:O-2494 structure.png O-2394 4-Me iBu pyrrolidinyl 850352-51-1
File:4-Me-PEP structure.png MPEP 4-Me pentyl pyrrolidinyl
File:4-F-PEP structure.png 4F-PV8 4-F pentyl pyrrolidinyl
File:4-MeO-PEP structure.png 4-MeO-PV8 4-MeO pentyl pyrrolidinyl
File:MFPEP structure.png MFPEP 3-Me-4-F pentyl pyrrolidinyl
File:MCPEP structure.png MCPEP 3-Me-4-Cl pentyl pyrrolidinyl
4F-PV9 4-F hexyl pyrrolidinyl
File:4-MeO-POP structure.png 4-MeO-PV9 4-MeO hexyl pyrrolidinyl
File:Alpha-phenylpyrovalerone structure.png α-Phenylpyrovalerone 4-Me phenyl pyrrolidinyl
MDPPP 3,4-methylenedioxy Me pyrrolidinyl 783241-66-7
File:MDMPP structure.png 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
File:2,3-MDPV structure.png 2,3-MDPV 2,3-methylenedioxy nPr pyrrolidinyl
File:5-Me-MDPV structure.png 5-Me-MDPV 3,4-methylenedioxy-5-Me nPr pyrrolidinyl
File:6-Me-MDPV structure.png 6-Me-MDPV 2-Me-4,5-methylenedioxy nPr pyrrolidinyl
File:6-MeO-MDPV structure.png 6-MeO-MDPV 2-MeO-4,5-methylenedioxy nPr pyrrolidinyl
File:4-MeO-5-Br-2,3-MDPV structure.png Br-MeO-MDPV 2,3-methylenedioxy-4-MeO-5-Br nPr pyrrolidinyl
File:MDPiVP structure.png MDPiVP 3,4-methylenedioxy iPr pyrrolidinyl
MDPHP 3,4-methylenedioxy nBu pyrrolidinyl 776994-64-0
File:MDPHiP structure.png MDPHiP 3,4-methylenedioxy iBu pyrrolidinyl
File:MDPEP structure.png MDPEP (MD-PV8) 3,4-methylenedioxy pentyl pyrrolidinyl 24646-39-7
File:MDPOP structure.png MDPOP (MD-PV9) 3,4-methylenedioxy hexyl pyrrolidinyl 24646-40-0
File:5-PPDI structure.png 5-PPDI 3,4-trimethylene Et pyrrolidinyl
File:5-BPDI structure.png 5-BPDI 3,4-trimethylene nPr pyrrolidinyl
File:5-HPDI structure.png 5-HPDI 3,4-trimethylene nBu pyrrolidinyl
IPPV 3,4-trimethylene phenyl pyrrolidinyl
File:TH-PBP structure.png TH-PBP 3,4-tetramethylene Et pyrrolidinyl
TH-PVP 3,4-tetramethylene nPr pyrrolidinyl 2304915-07-7
File:TH-PHP structure.png TH-PHP 3,4-tetramethylene nBu pyrrolidinyl
5-DBFPV 2,3-dihydrobenzofuran-5-yl instead of Ph nPr pyrrolidinyl 1620807-94-4
File:3-BF-PVP structure.png 3-BF-PVP benzofuran-3-yl instead of Ph nPr pyrrolidinyl
Naphyrone (O-2482) β-naphthyl instead of phenyl nPr pyrrolidinyl 850352-53-3
File:Alpha-naphyrone structure.png α-Naphyrone α-naphthyl instead of phenyl nPr pyrrolidinyl
File:Alpha-PPT structure.png α-PPT thiophen-2-yl instead of phenyl Me pyrrolidinyl
File:Alpha-PBT structure.png α-PBT thiophen-2-yl instead of phenyl Et pyrrolidinyl
α-PVT thiophen-2-yl instead of phenyl nPr pyrrolidinyl 1400742-66-6

Legality

On 2 April 2010, the Advisory Council on the Misuse of Drugs in the United Kingdom announced that a broad structure-based ban of this entire class of compounds would be instituted, following extensive publicity around grey-market sales and recreational use of mephedrone, a common member of the family. This ban covers compounds with the aforementioned general structure, with 28 compounds specifically named.[30]

"Any compound (not being bupropion or a substance for the time being specified in paragraph 2.2) structurally derived from 2-amino-1-phenyl-1-propanone by modification in any of the following ways, that is to say,

(i) by substitution in the phenyl ring to any extent with alkyl, alkoxy, alkylenedioxy, haloalkyl or halide substituents, whether or not further substituted in the phenyl ring by one or more other univalent substituents;

(ii) by substitution at the 3-position with an alkyl substituent;

(iii) by substitution at the nitrogen atom with alkyl or dialkyl groups, or by inclusion of the nitrogen atom in a cyclic structure."
—ACMD, 2 April 2010

This text was added as an amendment to the Misuse of Drugs Act 1971, to come into force on 16 April 2010.[31] Note that four of the above compounds (cathinone, methcathinone, diethylpropion and pyrovalerone) were already illegal in the UK at the time the ACMD report was issued. Two compounds were specifically excluded from the ban, these being bupropion because of its common use in medicine and relative lack of abuse potential, and naphyrone because its structure falls outside the generic definition and not enough evidence was yet available to justify a ban.

Naphyrone analogues were subsequently banned in July 2010 following a further review by the ACMD,[32][33] along with a further broad based structure ban even more expansive than the last.[34][35]

"Any compound structurally derived from 2–aminopropan–1–one by substitution at the 1-position with any monocyclic, or fused-polycyclic ring system (not being a phenyl ring or alkylenedioxyphenyl ring system), whether or not the compound is

further modified in any of the following ways, that is to say—

(i) by substitution in the ring system to any extent with alkyl, alkoxy, haloalkyl or halide substituents, whether or not further substituted in the ring system by one or more other univalent substituents;

(ii) by substitution at the 3–position with an alkyl substituent;

(iii) by substitution at the 2-amino nitrogen atom with alkyl or dialkyl groups, or

by inclusion of the 2-amino nitrogen atom in a cyclic structure".
—Home Office, 13 July 2010.
File:Naphyrone general.png
General chemical structure of substituted naphyrones, with R1-R3 defined in text

The substitutions in the general structure for naphyrone analogues subject to the ban may be described as follows:

  • Cyc = any monocyclic, or fused-polycyclic ring system (not being a phenyl ring or alkylenedioxyphenyl ring system), including analogues where the ring system is substituted to any extent with alkyl, alkoxy, haloalkyl or halide substituents, whether or not further substituted in the ring system by one or more other univalent substituents
  • R1 = hydrogen or any alkyl group
  • R2 = hydrogen, any alkyl group, or incorporation in a cyclic structure
  • R3 = hydrogen, any alkyl group, or incorporation in a cyclic structure

More new derivatives have however continued to appear, with the UK reporting more novel cathinone derivatives detected in 2010 than any other country in Europe, with most of them first identified after the generic ban had gone into effect and thus already being illegal despite never having been previously reported.[36]

In the United States, substituted cathinones are the psychoactive ingredients in "bath salts" which as of July 2011 were banned by at least 28 states, but not by the federal government.[37]

See also

References

  1. ↑ "1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors". Journal of Medicinal Chemistry 49 (4): 1420–32. February 2006. doi:10.1021/jm050797a. PMID 16480278. 
  2. ↑ "Emerging drugs of abuse: current perspectives on substituted cathinones". Substance Abuse and Rehabilitation 5: 37–52. 2014. doi:10.2147/SAR.S37257. PMID 24966713. 
  3. ↑ "DARK Classics in Chemical Neuroscience: Cathinone-Derived Psychostimulants". ACS Chemical Neuroscience 9 (10): 2379–2394. October 2018. doi:10.1021/acschemneuro.8b00147. PMID 29714473. 
  4. ↑ "Intoxications in the STRIDA project involving a panorama of psychostimulant pyrovalerone derivatives, MDPV copycats". Clinical Toxicology 56 (4): 256–263. April 2018. doi:10.1080/15563650.2017.1370097. PMID 28895757. 
  5. ↑ "The newest cathinone derivatives as designer drugs: an analytical and toxicological review". Forensic Toxicology 36 (1): 33–50. 2018. doi:10.1007/s11419-017-0385-6. PMID 29367861. 
  6. ↑ "Khat use is associated with impaired working memory and cognitive flexibility". PLOS ONE 6 (6): e20602. 2011. doi:10.1371/journal.pone.0020602. PMID 21698275. Bibcode: 2011PLoSO...620602C. 
  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. ↑ European Monitoring Center for Drugs and Drug Addiction (December 2020). New psychoactive substances: global markets, glocal threats and the COVID-19 pandemic. An update from the EU Early Warning System. Luxembourg: Publications Office of the European Union. doi:10.2810/921262. ISBN 9789294975584. https://www.emcdda.europa.eu/system/files/publications/13464/20205648_TD0320796ENN_PDF_rev.pdf. 
  18. ↑ "Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis". Therapeutic Drug Monitoring 26 (2): 127–31. April 2004. doi:10.1097/00007691-200404000-00007. PMID 15228152. 
  19. ↑ "The characterisation of two halogenated cathinone analogues: 3,5-difluoromethcathinone and 3,5-dichloromethcathinone". Forensic Science International 217 (1–3): 139–45. April 2012. doi:10.1016/j.forsciint.2011.10.042. PMID 22088945. 
  20. ↑ "Identification and analytical characterization of nine synthetic cathinone derivatives N-ethylhexedrone, 4-Cl-pentedrone, 4-Cl-α-EAPP, propylone, N-ethylnorpentylone, 6-MeO-bk-MDMA, α-PiHP, 4-Cl-α-PHP, and 4-F-α-PHP". Drug Testing and Analysis 9 (8): 1162–1171. August 2017. doi:10.1002/dta.2136. PMID 27863142. 
  21. ↑ "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 37 (2): 288–307. 2019. doi:10.1007/s11419-018-00463-w. 
  22. ↑ "Analytische Daten neuer 2-aminosubstituierter Methylendioxyvalerophenonderivate.". Toxichem Krimtech 83 (1): 3–29. January 2016. 
  23. ↑ "The newest cathinone derivatives as designer drugs: an analytical and toxicological review". Forensic Toxicology 36 (1): 33–50. 2018. doi:10.1007/s11419-017-0385-6. PMID 29367861. 
  24. ↑ "Prediction of designer drugs: Synthesis and spectroscopic analysis of synthetic cathinone analogs that may appear on the Swedish drug market". Drug Testing and Analysis 10 (7): 1076–1098. February 2018. doi:10.1002/dta.2366. PMID 29426062. 
  25. ↑ "Forensic drug analysis of chloro-N,N-dimethylcathinone (CDC) and chloroethcathinone (CEC): Identification of 4-CDC and 4-CEC in drug seizures and differentiation from their ring-substituted positional isomers". Forensic Science International 298: 268–277. May 2019. doi:10.1016/j.forsciint.2019.03.002. PMID 30925345. 
  26. ↑ "New psychoactive versus conventional stimulants - a ten-year review of casework in Hungary". Legal Medicine 47: 101780. November 2020. doi:10.1016/j.legalmed.2020.101780. PMID 32882537. 
  27. ↑ "Interpol review of controlled substances 2016-2019". Forensic Science International. Synergy 2: 608–669. 2020. doi:10.1016/j.fsisyn.2020.01.019. PMID 33385148. 
  28. ↑ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" (in Finnish). Finlex Data Bank. https://finlex.fi/fi/laki/ajantasa/2014/20141130#a12.11.2020-764. 
  29. ↑ Baggott M. Advantageous Tryptamine Compositions For Mental Disorders or Enhancement. Patent WO 2022/061242
  30. ↑ Advisory Council on the Misuse of Drugs (UK). Consideration of the cathinones. 31 March 2010. Retrieved 2011-07-17.
  31. ↑ "The Misuse of Drugs (Amendment) (England, Wales and Scotland) Regulations 2010 No. 1144". Opsi.gov.uk. http://www.opsi.gov.uk/si/si2010/uksi_20101144_en_1. 
  32. ↑ "NRG-1 'legal high' drug is banned". BBC News. 2010-07-12. http://news.bbc.co.uk/1/hi/uk/10602398.stm. 
  33. ↑ "Advisory Council on the Misuse of Drugs Naphyrone Report (2010)". Home Office. 2010-07-07. http://www.homeoffice.gov.uk/publications/drugs/acmd1/naphyrone-report. 
  34. ↑ "Explanatory Memorandum To The Misuse of Drugs (Amendment No. 2) (England, Wales and Scotland) Regulations 2010 No. 1799". Opsi.gov.uk. http://www.opsi.gov.uk/si/si2010/em/uksiem_20101799_en.pdf. 
  35. ↑ "The Misuse of Drugs (Amendment No. 2) (England, Wales and Scotland) Regulations 2010 No. 1799". Opsi.gov.uk. http://www.opsi.gov.uk/si/si2010/pdf/uksi_20101799_en.pdf. 
  36. ↑ European Monitoring Centre on Drugs and Drug Addiction. EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA. Retrieved 2011-07-17.
  37. ↑ "An Alarming New Stimulant, Legal in Many States.". The New York Times. 16 July 2011. https://www.nytimes.com/2011/07/17/us/17salts.html. 



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