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

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-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
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
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 structure.png
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
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
3-F-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
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
Ephylone structure.png
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 structure.png
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
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 structure.png
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
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
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
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

Legality

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.[29]

"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.[30] 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,[31][32] along with a further broad based structure ban even more expansive than the last.[33][34]

"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
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:

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.[35]

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.[36]

See also

References

  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.
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  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.
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  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.
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