Substituted cathinone

From Wikipedia, the free encyclopedia

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[edit]

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.svg Cathinone H Me H H 71031-15-7
Methcathinone skeletal.svg Methcathinone H Me H Me 5650-44-2
Ethcathinone.svg Ethcathinone H Me H Et 51553-17-4
Propylcathinone structure.png Propylcathinone H Me H nPr 52597-14-5
Buphedrone.svg Buphedrone H Et H Me 408332-79-6
N-Ethylbuphedrone.svg N-Ethylbuphedrone (NEB) H Et H Et 1354631-28-9
Methylethylbuphedrone structure.png N-Methyl-N-ethylbuphedrone H Et Me Et
Pentedrone.svg Pentedrone H nPr H Me 879722-57-3
N-Ethylpentedrone structure.png N-Ethylpentedrone H nPr H Et 18268-16-1
N-Isopropylpentedrone structure.png N-Isopropylpentedrone H nPr H iPr 18268-14-9
Hexedrone.png Hexedrone H nBu H Me 2169446-41-5
Ethylhexedrone.svg N-Ethylhexedrone H nBu H Et 18410-62-3
Butylhexedrone structure.png N-Butylhexedrone H nBu H nBu 18296-66-7
Isobutylhexedrone structure.png N-Isobutylhexedrone (NDH) H nBu H i-Bu
Isohexedrone structure.png Isohexedrone H iBu H Me
N-ethylheptedrone structure.png N-Ethylheptedrone H nPe H Et
Octedrone structure.png Octedrone H hexyl H Me
Dimethylcathinone.svg Dimethylcathinone H Me Me Me 15351-09-4
Amfepramone.svg Diethylpropion H Me Et Et 134-80-5
NN-methylethylcathinone structure.png N-Methyl-N-ethylcathinone H Me Me Et 1157739-24-6
Bupropion 1.svg Bupropion (3-CBP) 3-Cl Me H t-Bu 34911-55-2
Hydroxybupropion.svg Hydroxybupropion 3-Cl Me H 2-Me-3-OH-propan-2-yl 357399-43-0
4-Methylmethcathinone.svg Mephedrone 4-Me Me H Me 1189805-46-6
2-MMC structure.png 2-MMC 2-Me Me H Me 1246911-71-6
2-MEC structure.png 2-MEC 2-Me Me H Et 1439439-84-5
2-EMC structure.png 2-EMC 2-Et Me H Me
2-EEC structure.png 2-EEC 2-Et Me H Et 2446466-59-5
3-methylmethcathinone.svg 3-MMC 3-Me Me H Me 1246816-62-5
3-MEC structure.png 3-MEC 3-Me Me H Et 1439439-83-4
3-MPC structure.png 3-MPC 3-Me Me H nPr
3-EMC structure.png 3-EMC 3-Et Me H Me
3-EEC structure.png 3-EEC 3-Et Me H Et 2446466-61-9
4-ethylmethcathinone.png 4-EMC 4-Et Me H Me 1225622-14-9
4-EEC structure.png 4-EEC 4-Et Me H Et 2446466-62-0
4-Methylcathinone.png 4-MC 4-Me Me H H 31952-47-3
Benzedrone.svg Benzedrone 4-Me Me H Bn 1225617-75-3
2'-MeO-benzedrone structure.png 2'-MeO-Benzedrone 4-Me Me H 2-MeO-Bn
2,N-DM-Benzedrone structure.png 2,N-Dimethylbenzedrone 2-Me Me Me Bn
3,N-DM-Benzedrone structure.png 3,N-Dimethylbenzedrone 3-Me Me Me Bn
4,N-DM-Benzedrone structure.png 4,N-Dimethylbenzedrone 4-Me Me Me Bn
4-MEC.svg 4-MEC 4-Me Me H Et 1225617-18-4
4-methyl-propylcathinone structure.png 4-MPC 4-Me Me H nPr
NN-DMMC structure.png N,N-DMMC 4-Me Me Me Me 1448845-14-4
NN-MEMC structure.png N,N-MEMC 4-Me Me Me Et
NN-DEMC structure.png N,N-DEMC 4-Me Me Et Et 676316-90-8
4-MEAP.svg 4-MEAP 4-Me Pr H Et 746540-82-9
4-EDMC structure.png EDMC 4-Et Me Me Me
2,3-DMMC structure.png 2,3-DMMC 2,3-dimethyl Me H Me
2,3-DMEC structure.png 2,3-DMEC 2,3-dimethyl Me H Et
2,4-DMMC structure.png 2,4-DMMC 2,4-dimethyl Me H Me 1225623-63-1
2,4-DMEC structure.png 2,4-DMEC 2,4-dimethyl Me H Et 1225913-88-1
2,5-DMMC structure.png 2,5-DMMC 2,5-dimethyl Me H Me
2,5-DMEC structure.png 2,5-DMEC 2,5-dimethyl Me H Et
2,6-DMMC structure.png 2,6-DMMC 2,6-dimethyl Me H Me
2,6-DMEC structure.png 2,6-DMEC 2,6-dimethyl Me H Et
3,4-DMMC.svg 3,4-DMMC 3,4-dimethyl Me H Me 1082110-00-6
3,4-DMEC structure.png 3,4-DMEC 3,4-dimethyl Me H Et 1225811-81-3
3,5-DMEC structure.png 3,5-DMEC 3,5-dimethyl Me H Et
245-TMMC structure.png 2,4,5-TMMC 2,4,5-trimethyl Me H Me 1368603-85-3
245-TMOMC structure.png 2,4,5-TMOMC 2,4,5-trimethoxy Me H Me
345-TMOMC structure.png 3,4,5-TMOMC 3,4,5-trimethoxy Me H Me
4-Methoxymethcathinone.svg Methedrone 4-MeO Me H Me 530-54-1
Dimethedrone structure.png Dimethedrone 4-MeO Me Me Me 91564-39-5
Ethedrone structure.png Ethedrone 4-MeO Me H Et
2-MOMC structure.png 2-MOMC 2-MeO Me H Me
3-MOMC structure.png 3-MOMC 3-MeO Me H Me 1435933-70-2
3-fluorocathinone structure.png 3-FC 3-F Me H H 1082949-91-4
4-fluorocathinone structure.png 4-FC 4-F Me H H 80096-51-1
2-FMC structure.png 2-FMC 2-F Me H Me 1186137-35-8
2-FEC structure.png 2-FEC 2-F Me H Et
3-fluoromethcathinone.svg 3-FMC 3-F Me H Me 1049677-77-1
3-FEC structure.png 3-FEC 3-F Me H Et
2-CMC structure.png 2-CMC 2-Cl Me H Me
2-BMC structure.png 2-BMC 2-Br Me H Me
2-IMC structure.png 2-IMC 2-I Me H Me
2-TFMMC structure.png 2-TFMAP 2-CF3 Me H Me
3-Chloromethcathinone structure.png Clophedrone 3-Cl Me H Me 1049677-59-9
3-CEC structure.png 3-CEC 3-Cl Me H Et 2150476-60-9
3-BMC structure.png 3-BMC 3-Br Me H Me 676487-42-6
3-IMC structure.png 3-IMC 3-I Me H Me
3-TFMMC structure.png 3-TFMAP 3-CF3 Me H Me
4-fluoromethcathinone.svg Flephedrone 4-F Me H Me 447-40-5
4-Fluoroethcathinone Structure.svg 4-FEC 4-F Me H Et 1225625-74-0
4-Chloromethcathinone.png Clephedrone 4-Cl Me H Me 1225843-86-6
2Cl-NEC structure.png 2-CEC 2-Cl Me H Et
4-CEC structure.png 4-CEC 4-Cl Me H Et 14919-85-8
2Cl-NiPC structure.png 2-CiPC 2-Cl Me H iPr
3Cl-NiPC structure.png 3-CiPC 3-Cl Me H iPr
4-CiPC structure.png 4-CiPC 4-Cl Me H iPr
4-CBC structure.png 4-CBC 4-Cl Me H nBu 1225621-71-5
2Cl-DMC structure.png 2-CDMC 2-Cl Me Me Me
3Cl-DMC structure.png 3-CDMC 3-Cl Me Me Me
4-CDMC structure.png 4-CDMC 4-Cl Me Me Me 1157667-29-2
4-bromomethcathinone.svg Brephedrone 4-Br Me H Me 486459-03-4
4-BEC structure.png 4-BEC 4-Br Me H Et 135333-26-5
4-IMC structure.png 4-IMC 4-I Me H Me
4-TFMMC structure.png 4-TFMAP 4-CF3 Me H Me
4-EFMC structure.png 4-EFMC 4-(2-fluoroethyl) Me H Me
4-MTMC structure.png 4-MTMC 4-SCH3 Me H Me
4-MSMC structure.png 4-MSMC 4-SO2CH3 Me H Me
4-PHMC structure.png 4-PHMC 4-phenyl Me H Me
Mexedrone.svg Mexedrone 4-Me methoxymethyl H Me
3,4-FMMC structure.png FMMC 3-F-4-Me Me H Me 1696642-00-8
3,4-MFMC structure.png MFMC 3-Me-4-F Me H Me 1368943-21-8
4-Cl-3-MMC structure.png 4-Cl-3-MMC 3-Me-4-Cl Me H Me
3,4-MMOMC structure.png MMOMC 3-Me-4-MeO Me H Me
3,4-DCMC structure.png 3,4-DCMC 3,4-dichloro Me H Me 802281-39-6
3,4-DCEC structure.png 3,4-DCEC 3,4-dichloro Me H Et 1225618-63-2
3,5-DCMC structure.png 3,5-DCMC 3,5-dichloro Me H Me
3,5-DFMC structure.png 3,5-DFMC 3,5-difluoro Me H Me 1430343-55-7
2,5-DMOMC structure.png 2,5-DMOMC 2,5-dimethoxy Me H Me
Bk2CC structure.png βk-2C-C 2,5-dimethoxy-4-chloro H H H 1538191-15-9
Βk-2C-B-skeletal.svg βk-2C-B 2,5-dimethoxy-4-bromo H H H 807631-09-0
Bk2CI structure.png βk-2C-I 2,5-dimethoxy-4-iodo H H H
Bk2CD structure.png βk-2C-D 2,5-dimethoxy-4-methyl H H H 1368627-25-1
Bk2CE structure.png βk-2C-E 2,5-dimethoxy-4-ethyl H H H 1517021-02-1
Bk2CP structure.png βk-2C-P 2,5-dimethoxy-4-propyl H H H
Bk2CiP structure.png βk-2C-iP 2,5-dimethoxy-4-isopropyl H H H 1511033-62-7
BkDOB structure.png βk-DOB 2,5-dimethoxy-4-bromo Me H H
BkMDOM structure.png βk-MDOM 2,5-dimethoxy-4-methyl Me H Me
MDC.png βk-MDA 3,4-methylenedioxy Me H H 80535-73-5
BkMDAc structure.png N-Acetyl-βk-MDA 3,4-methylenedioxy Me H acetyl
2,3-MDMC structure.png 2,3-MDMC 2,3-methylenedioxy Me H Me 1427205-87-5
Methylone.svg Methylone 3,4-methylenedioxy Me H Me 186028-79-5
Dimethylone.svg Dimethylone 3,4-methylenedioxy Me Me Me 109367-07-9
NAc-Methylone structure.png N-Acetylmethylone 3,4-methylenedioxy Me acetyl Me
NOH-Methylone structure.png N-Hydroxymethylone 3,4-methylenedioxy Me hydroxy Me
Bk-MDEA.svg Ethylone 3,4-methylenedioxy Me H Et 1112937-64-0
Diethylone structure.png Diethylone 3,4-methylenedioxy Me Et Et
NAc-Ethylone structure.png N-Acetylethylone 3,4-methylenedioxy Me acetyl Et
BkMDiP structure.png N-Isopropyl-βk-MDA 3,4-methylenedioxy Me H iPr
BkMDtB structure.png MDPT 3,4-methylenedioxy Me H t-Bu 186028-84-2
BMDP structure.png Benzylone (BMDP) 3,4-methylenedioxy Me H Bn 1823274-68-5
N-Cyclohexylmethylone structure.png N-Cyclohexylmethylone 3,4-methylenedioxy Me H cyclohexyl
3,4-EDMC structure.png 3,4-EDMC 3,4-ethylenedioxy Me H Me 30253-44-2
BkIMP structure.png βk-IMP 3,4-trimethylene Me H Me 100608-69-3
BkIEB structure.png βk-IBP 3,4-trimethylene Et H Et
BkIEV structure.png βk-IVP 3,4-trimethylene nPr H Et
3-fluorobuphedrone structure.png 3-Fluorobuphedrone 3-F Et H Me
4-fluorobuphedrone structure.png 4-Fluorobuphedrone 4-F Et H Me 1368599-12-5
4-bromobuphedrone structure.png 4-Bromobuphedrone 4-Br Et H Me
3-Methylbuphedrone structure.png 3-Methylbuphedrone 3-Me Et H Me 1797911-07-9
4-Methylbuphedrone.png 4-Me-MABP 4-Me Et H Me 1336911-98-8
4-Me-NEB structure.png 4-Me-NEB 4-Me Et H Et 18268-19-4
2F-NEB structure.png 2-F-NEB 2-F Et H Et
3F-NEB structure.png 3F-NEB 3-F Et H Et
4-F-NEB structure.png 4-F-NEB 4-F Et H Et
4-Me-DMB structure.png 4-Me-DMB 4-Me Et Me Me
3,4-DMEB structure.png 3,4-DMEB 3,4-dimethyl Et H Et
4-methoxybuphedrone structure.png 4-Methoxybuphedrone 4-MeO Et H Me
Bk-MBDB.svg Butylone 3,4-methylenedioxy Et H Me 802575-11-7
Eutylone.svg Eutylone 3,4-methylenedioxy Et H Et 802855-66-9
BkPBDB structure.png βk-PBDB 3,4-methylenedioxy Et H nPr
Bn-4-Me-MABP structure.png Bn-4-MeMABP 4-Me Et H Bn 1445751-39-2
BMDB structure.png BMDB 3,4-methylenedioxy Et H Bn 1445751-47-2
N-Cyclohexylbutylone structure.png N-Cyclohexylbutylone 3,4-methylenedioxy Et H cyclohexyl
Dibutylone.svg βk-DMBDB 3,4-methylenedioxy Et Me Me 802286-83-5
BkMMDMA structure.png βk-MMDMA 3,4-methylenedioxy-5-MeO Me H Me 2230716-98-8
2-methoxymethylone structure.png βk-MMDMA-2 2-MeO-3,4-methylenedioxy Me H Me
BkDMMDA structure.png βk-DMMDA 2,5-diMeO-3,4-methylenedioxy Me H H
5-methylmethylone structure.png 5-Methylmethylone 3,4-methylenedioxy-5-Me Me H Me 1364933-83-4
5-Methylethylone.svg 5-Methylethylone 3,4-methylenedioxy-5-Me Me H Et 1364933-82-3
2-methylbutylone structure.png 2-Methylbutylone 2-Me-3,4-methylenedioxy Et H Me 1364933-86-7
5-methylbutylone structure.png 5-Methylbutylone 3,4-methylenedioxy-5-Me Et H Me 1354631-29-0
Pentylone.svg Pentylone 3,4-methylenedioxy nPr H Me 698963-77-8
N-Ethylpentylone.svg N-Ethylpentylone 3,4-methylenedioxy nPr H Et 727641-67-0
N-propylpentylone structure.png N-propylpentylone 3,4-methylenedioxy nPr H nPr
N-butylpentylone structure.png N-butylpentylone 3,4-methylenedioxy nPr H nBu
2,3-Dipentylone structure.png 2,3-Dipentylone 2,3-methylenedioxy nPr Me Me
Dipentylone.svg Dipentylone 3,4-methylenedioxy nPr Me Me 17763-13-2
NN-diethyl-pentylone structure.png N,N-Diethylnorpentylone 3,4-methylenedioxy nPr Et Et
Hexylone structure.png Hexylone 3,4-methylenedioxy nBu H Me
Isohexylone structure.png Isohexylone 3,4-methylenedioxy iBu H Me 1157947-89-1
Isoheptylone structure.png Isoheptylone 3,4-methylenedioxy iPe H Me
N-ethylhexylone structure.png N-Ethylhexylone 3,4-methylenedioxy nBu H Et 27912-41-0
N-ethylheptylone structure.png N-Ethylheptylone 3,4-methylenedioxy nPe H Et
4-MEAP.svg 4-MEAP 4-Me nPr H Et 746540-82-9
3,4-DMEP structure.png 3,4-DMEP 3,4-dimethyl nPr H Et
2F-Pentedrone structure.png 2-F-Pentedrone 2-F nPr H Me
3F-Pentedrone structure.png 3-F-Pentedrone 3-F nPr H Me
4-fluoropentedrone structure.png 4-F-Pentedrone 4-F nPr H Me
4-chloropentedrone structure.png 4-Cl-Pentedrone 4-Cl nPr H Me 2167949-43-9
4-Methylpentedrone.png 4-Methylpentedrone 4-Me nPr H Me 1373918-61-6
DL-4662 structure.png DL-4662 3,4-dimethoxy nPr H Et 1674389-55-9
4F-NiP-pentedrone structure.png 4-F-iPr-norpentedrone 4-F nPr H iPr
4Cl-NtB-pentedrone structure.png 3-CBV 3-Cl nPr H tBu
4-methylhexedrone structure.png 4-methylhexedrone 4-Me nBu H Me
4-methyl-N-ethylhexedrone structure.png MEH 4-Me nBu H Et
3F-NEH structure.png 3F-NEH 3-F nBu H Et
4-fluorohexedrone structure.png 4-F-hexedrone 4-F nBu H Me
4-fluorooctedrone structure.png 4-F-octedrone 4-F hexyl H Me
Alpha-phenylmephedrone structure.png α-phenylmephedrone 4-Me phenyl H Me
Bk-EPE structure.png βk-Ephenidine H phenyl H Et 22312-16-9
Bk-methamnetamine.svg BMAPN β-naphthyl instead of phenyl Me H Me
Thiothinone.svg βk-Methiopropamine thiophen-2-yl instead of phenyl Me H Me 24065-17-6
5ClbkMPA structure.png 5-Cl-bk-MPA 5-chlorothiophen-2-yl instead of phenyl Me H Me
Bk-5-MAPB structure.png βk-5-MAPB benzofuran-5-yl instead of phenyl Me H Me
Bk-6-MAPB structure.png βk-6-MAPB benzofuran-6-yl instead of phenyl Me H Me
Bk-5-IT structure.png βk-5-IT indol-5-yl instead of phenyl Me H H 1369231-36-6
BK-5F-NM-AMT structure.png βk-5F-NM-AMT[29] 5-fluoroindol-3-yl instead of phenyl Me H Me
Phthalprop.svg α-Phthalimidopropiophenone H Me phthalimido 19437-20-8
PPPO structure.png PPPO H Me piperidinyl
PPBO structure.png PPBO H Et piperidinyl 92728-82-0
FPPVO structure.png FPPVO 4-F nPr piperidinyl
MDPV-azepane structure.png MDPV-azepane 3,4-methylenedioxy nPr azepane
Caccure907 structure.png Caccure 907 4-SCH3 α,α-di-Me morpholinyl
A-PPP.svg α-PPP H Me pyrrolidinyl 19134-50-0
Α-PBP.svg α-PBP H Et pyrrolidinyl 13415-54-8
Alpha-Pyrrolidinopentiophenone.svg α-PVP (O-2387) H nPr pyrrolidinyl 14530-33-7
Α-PHP.svg α-PHP H nBu pyrrolidinyl 13415-86-6
Alpha-PHiP structure.png α-PHiP H iBu pyrrolidinyl
Alpha-Pyrrolidinoheptaphenone.svg α-PEP (α-PHPP) H nPe pyrrolidinyl 13415-83-3
Alpha-POP structure.png α-POP H hexyl pyrrolidinyl
Alpha-PNP structure.png α-PNP H heptyl pyrrolidinyl
Diphenylpyrrolidinylethanone structure.png DPPE (A-D2PV) H phenyl pyrrolidinyl 27590-61-0
Alpha-PcPeP structure.png α-PcPeP H cyclopentyl pyrrolidinyl
Alpha-PCYP structure.png α-PCYP H cyclohexyl pyrrolidinyl 1803168-11-7
2-Me-PPP structure.png 2-MePPP 2-Me Me pyrrolidinyl 2092429-83-7
3-Me-PPP structure.png 3-MePPP 3-Me Me pyrrolidinyl 1214940-01-8
PMPPP.svg 4-MePPP 4-Me Me pyrrolidinyl 1313393-58-6
3MeO-PPP structure.png 3-MeO-PPP 3-MeO Me pyrrolidinyl
MOPPP SVG.svg MOPPP 4-MeO Me pyrrolidinyl 478243-09-3
3-F-PPP structure.png 3-F-PPP 3-F Me pyrrolidinyl 1214939-99-7
4-F-PPP structure.png FPPP 4-F Me pyrrolidinyl 28117-76-2
4-Cl-PPP structure.png Cl-PPP 4-Cl Me pyrrolidinyl 93307-24-5
4Br-PPP structure.png Br-PPP 4-Br Me pyrrolidinyl
2,3-DMPPP structure.png 2,3-DMPPP 2,3-dimethyl Me pyrrolidinyl
2,4-DMPPP structure.png 2,4-DMPPP 2,4-dimethyl Me pyrrolidinyl
3,4-DMPPP structure.png 3,4-DMPPP 3,4-dimethyl Me pyrrolidinyl
3-Me-PBP structure.png 3-MPBP 3-Me Et pyrrolidinyl 1373918-60-5
3-F-PBP structure.png 3-F-PBP 3-F Et pyrrolidinyl 1373918-59-2
MPBP.svg MPBP 4-Me Et pyrrolidinyl 732180-91-5
4-F-PBP structure.png FPBP 4-F Et pyrrolidinyl 1373918-67-2
4-Et-PBP structure.png EPBP 4-Et Et pyrrolidinyl
4-MeO-PBP structure.png MOPBP 4-MeO Et pyrrolidinyl
MMOPBP structure.png MMOPBP 3-Me-4-MeO Et pyrrolidinyl
O-2384 structure.png O-2384 3,4-dichloro Et pyrrolidinyl 850352-65-7
2Me-PVP structure.png 2-Me-PVP 2-Me nPr pyrrolidinyl
Pyrovalerone.svg Pyrovalerone (O-2371) 4-Me nPr pyrrolidinyl 3563-49-3
4-Et-PVP structure.png 4-Et-PVP 4-Et nPr pyrrolidinyl
3-F-PVP structure.png 3F-PVP 3-F nPr pyrrolidinyl
FPVP.svg FPVP 4-F nPr pyrrolidinyl 850352-31-7
2Cl-PVP structure.png 2-Cl-PVP 2-Cl nPr pyrrolidinyl
3Cl-PVP structure.png 3-Cl-PVP 3-Cl nPr pyrrolidinyl
4-Cl-PVP structure.png 4-Cl-PVP 4-Cl nPr pyrrolidinyl 5537-17-7
4-Br-PVP structure.png 4-Br-PVP 4-Br nPr pyrrolidinyl
MOPVP.svg MOPVP 4-MeO nPr pyrrolidinyl 5537-19-9
DMPVP.svg DMOPVP 3,4-dimethoxy nPr pyrrolidinyl 850442-84-1
3,4-DMPVP structure.png DMPVP 3,4-dimethyl nPr pyrrolidinyl
O-2390 structure.png O-2390 3,4-dichloro nPr pyrrolidinyl 850352-61-3
MFPVP structure.png MFPVP 3-methyl-4-fluoro nPr pyrrolidinyl
MPHP.svg MPHP 4-Me nBu pyrrolidinyl 34138-58-4
3F-PHP structure.png 3F-PHP 3-F nBu pyrrolidinyl
4-F-PHP structure.png FPHP 4-F nBu pyrrolidinyl 2230706-09-7
4-Cl-PHP structure.png 4-Cl-PHP 4-Cl nBu pyrrolidinyl
DMOPHP structure.png DMOPHP 3,4-dimethoxy nBu pyrrolidinyl
MFPHP structure.png MFPHP 3-Me-4-F nBu pyrrolidinyl
3-F-PiHP structure.png 3F-PiHP 3-F iBu pyrrolidinyl
4-F-PiHP structure.png 4F-PiHP 4-F iBu pyrrolidinyl
O-2494 structure.png O-2394 4-Me iBu pyrrolidinyl 850352-51-1
4-Me-PEP structure.png MPEP 4-Me pentyl pyrrolidinyl
4-F-PEP structure.png 4F-PV8 4-F pentyl pyrrolidinyl
4-MeO-PEP structure.png 4-MeO-PV8 4-MeO pentyl pyrrolidinyl
FPOP.svg 4F-PV9 4-F hexyl pyrrolidinyl
4-MeO-POP structure.png 4-MeO-PV9 4-MeO hexyl pyrrolidinyl
Alpha-phenylpyrovalerone structure.png α-Phenylpyrovalerone 4-Me phenyl pyrrolidinyl
MDPPP.svg MDPPP 3,4-methylenedioxy Me pyrrolidinyl 783241-66-7
MDMPP structure.png MDMPP 3,4-methylenedioxy α,α-di-Me pyrrolidinyl
3',4'-Methylenedioxy-α-pyrrolidinobutiophenone.svg MDPBP 3,4-methylenedioxy Et pyrrolidinyl 784985-33-7
MDPV.svg MDPV 3,4-methylenedioxy nPr pyrrolidinyl 687603-66-3
2,3-MDPV structure.png 2,3-MDPV 2,3-methylenedioxy nPr pyrrolidinyl
5-Me-MDPV structure.png 5-Me-MDPV 3,4-methylenedioxy-5-Me nPr pyrrolidinyl
6-Me-MDPV structure.png 6-Me-MDPV 2-Me-4,5-methylenedioxy nPr pyrrolidinyl
6-MeO-MDPV structure.png 6-MeO-MDPV 2-MeO-4,5-methylenedioxy nPr pyrrolidinyl
4-MeO-5-Br-2,3-MDPV structure.png Br-MeO-MDPV 2,3-methylenedioxy-4-MeO-5-Br nPr pyrrolidinyl
MDPiVP structure.png MDPiVP 3,4-methylenedioxy iPr pyrrolidinyl
MDPHP.svg MDPHP 3,4-methylenedioxy nBu pyrrolidinyl 776994-64-0
MDPHiP structure.png MDPHiP 3,4-methylenedioxy iBu pyrrolidinyl
MDPEP structure.png MDPEP (MD-PV8) 3,4-methylenedioxy pentyl pyrrolidinyl 24646-39-7
MDPOP structure.png MDPOP (MD-PV9) 3,4-methylenedioxy hexyl pyrrolidinyl 24646-40-0
5-PPDI structure.png 5-PPDI 3,4-trimethylene Et pyrrolidinyl
5-BPDI structure.png 5-BPDI 3,4-trimethylene nPr pyrrolidinyl
5-HPDI structure.png 5-HPDI 3,4-trimethylene nBu pyrrolidinyl
Indapyrophenidone.svg IPPV 3,4-trimethylene phenyl pyrrolidinyl
TH-PBP structure.png TH-PBP 3,4-tetramethylene Et pyrrolidinyl
TH-PVP structure.png TH-PVP 3,4-tetramethylene nPr pyrrolidinyl 2304915-07-7
TH-PHP structure.png TH-PHP 3,4-tetramethylene nBu pyrrolidinyl
5-DBFPV.svg 5-DBFPV 2,3-dihydrobenzofuran-5-yl instead of Ph nPr pyrrolidinyl 1620807-94-4
3-BF-PVP structure.png 3-BF-PVP benzofuran-3-yl instead of Ph nPr pyrrolidinyl
Naphyrone.svg Naphyrone (O-2482) β-naphthyl instead of phenyl nPr pyrrolidinyl 850352-53-3
Alpha-naphyrone structure.png α-Naphyrone α-naphthyl instead of phenyl nPr pyrrolidinyl
Alpha-PPT structure.png α-PPT thiophen-2-yl instead of phenyl Me pyrrolidinyl
Alpha-PBT structure.png α-PBT thiophen-2-yl instead of phenyl Et pyrrolidinyl
Α-PVT.svg α-PVT thiophen-2-yl instead of phenyl nPr pyrrolidinyl 1400742-66-6


On 2 April 2010, the Advisory Council on the Misuse of Drugs in the UK 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.
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[edit]


  1. ^ Meltzer PC, Butler D, Deschamps JR, Madras BK (February 2006). "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. doi:10.1021/jm050797a. PMC 2602954. PMID 16480278.
  2. ^ Paillet-Loilier M, Cesbron A, Le Boisselier R, Bourgine J, Debruyne D (2014). "Emerging drugs of abuse: current perspectives on substituted cathinones". Substance Abuse and Rehabilitation. 5: 37–52. doi:10.2147/SAR.S37257. PMC 4043811. PMID 24966713.
  3. ^ Simmons SJ, Leyrer-Jackson JM, Oliver CF, Hicks C, Muschamp JW, Rawls SM, Olive MF (October 2018). "DARK Classics in Chemical Neuroscience: Cathinone-Derived Psychostimulants". ACS Chemical Neuroscience. 9 (10): 2379–2394. doi:10.1021/acschemneuro.8b00147. PMC 6197900. PMID 29714473.
  4. ^ 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): 256–263. doi:10.1080/15563650.2017.1370097. PMID 28895757. S2CID 3401681.
  5. ^ Majchrzak M, Celiński R, Kuś P, Kowalska T, Sajewicz M (2018). "The newest cathinone derivatives as designer drugs: an analytical and toxicological review". Forensic Toxicology. 36 (1): 33–50. doi:10.1007/s11419-017-0385-6. PMC 5754390. PMID 29367861.
  6. ^ Colzato LS, Ruiz MJ, van den Wildenberg WP, Hommel B (2011). "Khat use is associated with impaired working memory and cognitive flexibility". PLOS One. 6 (6): e20602. Bibcode:2011PLoSO...620602C. doi:10.1371/journal.pone.0020602. PMC 3115937. PMID 21698275.
  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 (PDF). Luxembourg: Publications Office of the European Union. doi:10.2810/921262. ISBN 9789294975584.
  18. ^ Maurer HH, Kraemer T, Springer D, Staack RF (April 2004). "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. doi:10.1097/00007691-200404000-00007. PMID 15228152. S2CID 9255084.
  19. ^ Davis S, Rands-Trevor K, Boyd S, Edirisinghe M (April 2012). "The characterisation of two halogenated cathinone analogues: 3,5-difluoromethcathinone and 3,5-dichloromethcathinone". Forensic Science International. 217 (1–3): 139–45. doi:10.1016/j.forsciint.2011.10.042. PMID 22088945.
  20. ^ Liu C, Jia W, Li T, Hua Z, Qian Z (August 2017). "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. doi:10.1002/dta.2136. PMID 27863142.
  21. ^ Błażewicz A, Bednarek E, Popławska M, Olech N, Sitkowski J, Kozerski L (2019). "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. doi:10.1007/s11419-018-00463-w. S2CID 59618061.
  22. ^ Westphal F, Girreser U, Angerer V, Auwärter V (January 2016). "Analytische Daten neuer 2-aminosubstituierter Methylendioxyvalerophenonderivate". Toxichem Krimtech. 83 (1): 3–29.
  23. ^ Majchrzak M, Celiński R, Kuś P, Kowalska T, Sajewicz M (2018). "The newest cathinone derivatives as designer drugs: an analytical and toxicological review". Forensic Toxicology. 36 (1): 33–50. doi:10.1007/s11419-017-0385-6. PMC 5754390. PMID 29367861.
  24. ^ Carlsson A, Sandgren V, Svensson S, Konradsson P, Dunne S, Josefsson M, Dahlén J (February 2018). "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. doi:10.1002/dta.2366. PMID 29426062.
  25. ^ Cheng WC, Wong WC (May 2019). "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. doi:10.1016/j.forsciint.2019.03.002. PMID 30925345.
  26. ^ Lajtai A, Mayer M, Lakatos Á, Kuzma M, Miseta A (November 2020). "New psychoactive versus conventional stimulants - a ten-year review of casework in Hungary". Legal Medicine. 47: 101780. doi:10.1016/j.legalmed.2020.101780. PMID 32882537. S2CID 221496728.
  27. ^ Jones NS, Comparin JH (2020). "Interpol review of controlled substances 2016-2019". Forensic Science International. Synergy. 2: 608–669. doi:10.1016/j.fsisyn.2020.01.019. PMC 7770462. PMID 33385148.
  28. ^ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" [Government Decree on Psychoactive Substances Banned from the Consumer Market]. Finlex Data Bank (in Finnish).
  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. Archived 22 September 2011 at the Wayback Machine Retrieved 2011-07-17.
  31. ^ "The Misuse of Drugs (Amendment) (England, Wales and Scotland) Regulations 2010 No. 1144". Retrieved 8 April 2010.
  32. ^ "NRG-1 'legal high' drug is banned". BBC News. 12 July 2010. Retrieved 17 July 2010.
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  34. ^ "Explanatory Memorandum To The Misuse of Drugs (Amendment No. 2) (England, Wales and Scotland) Regulations 2010 No. 1799" (PDF). Retrieved 18 July 2010.
  35. ^ "The Misuse of Drugs (Amendment No. 2) (England, Wales and Scotland) Regulations 2010 No. 1799" (PDF). Retrieved 18 July 2010.
  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. ^ Goodnough A, Zezima K (16 July 2011). "An Alarming New Stimulant, Legal in Many States". The New York Times. Retrieved 17 July 2011.