Substituted cathinone

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Cathinone Cathinone.svg
Cathinone
General chemical structure of substituted cathinones, with R1-R4 defined in text Substituted cathinone.svg
General chemical structure of substituted cathinones, with R1-R4 defined in text

Substituted cathinones, or simply 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]

Contents

Substituted cathinones act as monoamine releasing agents and/or monoamine reuptake inhibitors, including of norepinephrine, dopamine, and/or serotonin. [7] [8] [9] [10] [11] [12] In contrast to substituted amphetamines, substituted cathinones do not act as agonists of the human trace amine-associated receptor 1 (TAAR1). [13] [14] [15] This may potentiate their stimulating and addictive effects. [13] [14]

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: [16] [17] [18] [19] [20] [21] [22] [23] [24] [25] [26] [27] [28] [29] [30] [31] [32] [33] [34] [35] [36] [37]


StructureCompoundR1R2R3R4CAS number
Cathinone.svg Cathinone H Me H H 71031-15-7
Methcathinone skeletal.svg Methcathinone HMeHMe5650-44-2
Ethcathinone.svg Ethcathinone HMeH Et 51553-17-4
Propylcathinone structure.png PropylcathinoneHMeH nPr 52597-14-5
Buphedrone.svg Buphedrone HEtHMe408332-79-6
N-Ethylbuphedrone.svg N-Ethylbuphedrone (NEB)HEtHEt1354631-28-9
Methylethylbuphedrone structure.png N-Methyl-N-ethylbuphedroneHEtMeEt
Pentedrone.svg Pentedrone HnPrHMe879722-57-3
N-Ethylpentedrone structure.png N-Ethylpentedrone HnPrHEt18268-16-1
N-Isopropylpentedrone structure.png N-IsopropylpentedroneHnPrHiPr18268-14-9
Hexedrone.png Hexedrone HnBuHMe2169446-41-5
Ethylhexedrone.svg N-Ethylhexedrone HnBuHEt18410-62-3
Butylhexedrone structure.png N-ButylhexedroneHnBuHnBu18296-66-7
Isobutylhexedrone structure.png N-Isobutylhexedrone (NDH)HnBuH i-Bu
Isohexedrone structure.png IsohexedroneHiBuHMe
N-ethylheptedrone structure.png N-Ethylheptedrone HnPeHEt
Octedrone structure.png OctedroneH hexyl HMe
Dimethylcathinone.svg Dimethylcathinone HMeMeMe15351-09-4
Amfepramone.svg Diethylpropion HMeEtEt134-80-5
NN-methylethylcathinone structure.png N-Methyl-N-ethylcathinoneHMeMeEt1157739-24-6
Bupropion 1.svg Bupropion 3-ClMeH t-Bu 34911-55-2
Hydroxybupropion.svg Hydroxybupropion 3-ClMeH2-Me-3-OH-propan-2-yl357399-43-0
4-Methylmethcathinone.svg Mephedrone 4-MeMeHMe1189805-46-6
2-MMC structure.png 2-MMC 2-MeMeHMe1246911-71-6
2-MEC structure.png 2-MEC2-MeMeHEt1439439-84-5
2-EMC structure.png 2-EMC2-EtMeHMe
2-EEC structure.png 2-EEC2-EtMeHEt2446466-59-5
3-methylmethcathinone.svg 3-MMC 3-MeMeHMe1246816-62-5
3-MEC structure.png 3-MEC3-MeMeHEt1439439-83-4
3-MPC structure.png 3-MPC3-MeMeHnPr
3-EMC structure.png 3-EMC3-EtMeHMe
3-EEC structure.png 3-EEC3-EtMeHEt2446466-61-9
4-Ethylmethcathinone.svg 4-EMC 4-EtMeHMe1225622-14-9
4-EEC structure.png 4-EEC4-EtMeHEt2446466-62-0
4-Methylcathinone.png 4-MC 4-MeMeHH31952-47-3
Benzedrone.svg Benzedrone 4-MeMeH Bn 1225617-75-3
2'-MeO-benzedrone structure.png 2'-MeO-Benzedrone4-MeMeH2-MeO-Bn
2,N-DM-Benzedrone structure.png 2,N-Dimethylbenzedrone2-MeMeMeBn
3,N-DM-Benzedrone structure.png 3,N-Dimethylbenzedrone3-MeMeMeBn
4,N-DM-Benzedrone structure.png 4,N-Dimethylbenzedrone4-MeMeMeBn
4-MEC.svg 4-MEC 4-MeMeHEt1225617-18-4
4-methyl-propylcathinone structure.png 4-MPC4-MeMeHnPr
NN-DMMC structure.png N,N-DMMC4-MeMeMeMe1448845-14-4
NN-MEMC structure.png N,N-MEMC4-MeMeMeEt
NN-DEMC structure.png N,N-DEMC4-MeMeEtEt676316-90-8
4-MEAP.svg 4-MEAP 4-MePrHEt746540-82-9
4-EDMC structure.png EDMC4-EtMeMeMe
2,3-DMMC structure.png 2,3-DMMC2,3-dimethylMeHMe
2,3-DMEC structure.png 2,3-DMEC2,3-dimethylMeHEt
2,4-DMMC structure.png 2,4-DMMC2,4-dimethylMeHMe1225623-63-1
2,4-DMEC structure.png 2,4-DMEC2,4-dimethylMeHEt1225913-88-1
2,5-DMMC structure.png 2,5-DMMC2,5-dimethylMeHMe
2,5-DMEC structure.png 2,5-DMEC2,5-dimethylMeHEt
2,6-DMMC structure.png 2,6-DMMC2,6-dimethylMeHMe
2,6-DMEC structure.png 2,6-DMEC2,6-dimethylMeHEt
3,4-DMMC.svg 3,4-DMMC 3,4-dimethylMeHMe1082110-00-6
3,4-DMEC structure.png 3,4-DMEC3,4-dimethylMeHEt1225811-81-3
3,5-DMEC structure.png 3,5-DMEC3,5-dimethylMeHEt
245-TMMC structure.png 2,4,5-TMMC2,4,5-trimethylMeHMe1368603-85-3
245-TMOMC structure.png 2,4,5-TMOMC2,4,5-trimethoxyMeHMe
345-TMOMC structure.png 3,4,5-TMOMC3,4,5-trimethoxyMeHMe
4-Methoxymethcathinone.svg Methedrone 4-MeO MeHMe530-54-1
Dimethedrone structure.png Dimethedrone4-MeO MeMeMe91564-39-5
Ethedrone structure.png Ethedrone4-MeOMeHEt
2-MOMC structure.png 2-MOMC2-MeOMeHMe
3-MOMC structure.png 3-MOMC3-MeOMeHMe1435933-70-2
3-fluorocathinone structure.png 3-FC3-FMeHH1082949-91-4
4-fluorocathinone structure.png 4-FC4-FMeHH80096-51-1
2-FMC structure.png 2-FMC2-FMeHMe1186137-35-8
2-FEC structure.png 2-FEC2-FMeHEt
3-fluoromethcathinone.svg 3-FMC 3-FMeHMe1049677-77-1
3-FEC structure.png 3-FEC3-FMeHEt
2-CMC structure.png 2-CMC2-ClMeHMe
2-BMC structure.png 2-BMC2-BrMeHMe
2-IMC structure.png 2-IMC2-IMeHMe
2-TFMMC structure.png 2-TFMAP2-CF3MeHMe
3-Chloromethcathinone structure.png Clophedrone 3-ClMeHMe1049677-59-9
3-CEC structure.png 3-CEC 3-ClMeHEt2150476-60-9
3-BMC structure.png 3-BMC3-BrMeHMe676487-42-6
3-IMC structure.png 3-IMC3-IMeHMe
3-TFMMC structure.png 3-TFMAP3-CF3MeHMe
4-fluoromethcathinone.svg Flephedrone 4-F MeHMe447-40-5
4-Fluoroethcathinone Structure.svg 4-FEC 4-FMeHEt1225625-74-0
4-Chloromethcathinone.png Clephedrone 4-ClMeHMe1225843-86-6
2Cl-NEC structure.png 2-CEC2-ClMeHEt
4-CEC structure.png 4-CEC4-ClMeHEt14919-85-8
2Cl-NiPC structure.png 2-CiPC2-ClMeHiPr
3Cl-NiPC structure.png 3-CiPC3-ClMeHiPr
4-CiPC structure.png 4-CiPC4-ClMeHiPr
4-CBC structure.png 4-CBC4-ClMeHnBu1225621-71-5
2Cl-DMC structure.png 2-CDMC2-ClMeMeMe
3Cl-DMC structure.png 3-CDMC3-ClMeMeMe
4-CDMC structure.png 4-CDMC4-ClMeMeMe1157667-29-2
4-bromomethcathinone.svg Brephedrone 4-Br MeHMe486459-03-4
4-BEC structure.png 4-BEC4-BrMeHEt135333-26-5
4-IMC structure.png 4-IMC4-IMeHMe
4-TFMMC structure.png 4-TFMAP4-CF3MeHMe
4-EFMC structure.png 4-EFMC4-(2-fluoroethyl)MeHMe
4-MTMC structure.png 4-MTMC4-SCH3MeHMe
4-MSMC structure.png 4-MSMC4-SO2CH3MeHMe
4-PHMC structure.png 4-PHMC4-phenylMeHMe
Mexedrone.svg Mexedrone 4-MemethoxymethylHMe
3,4-FMMC structure.png FMMC3-F-4-MeMeHMe1696642-00-8
3,4-MFMC structure.png MFMC3-Me-4-FMeHMe1368943-21-8
4-Cl-3-MMC structure.png 4-Cl-3-MMC 3-Me-4-ClMeHMe
3,4-MMOMC structure.png MMOMC3-Me-4-MeOMeHMe
3,4-DCMC structure.png 3,4-DCMC3,4-dichloroMeHMe802281-39-6
3,4-DCEC structure.png 3,4-DCEC3,4-dichloroMeHEt1225618-63-2
3,5-DCMC structure.png 3,5-DCMC3,5-dichloroMeHMe
3,5-DFMC structure.png 3,5-DFMC 3,5-difluoroMeHMe1430343-55-7
2,5-DMOMC structure.png 2,5-DMOMC2,5-dimethoxyMeHMe
Bk2CC structure.png βk-2C-C2,5-dimethoxy-4-chloroHHH1538191-15-9
Bk-2C-B-skeletal.svg βk-2C-B 2,5-dimethoxy-4-bromoHHH807631-09-0
Bk2CI structure.png βk-2C-I2,5-dimethoxy-4-iodoHHH
Bk2CD structure.png βk-2C-D2,5-dimethoxy-4-methylHHH1368627-25-1
Bk2CE structure.png βk-2C-E2,5-dimethoxy-4-ethylHHH1517021-02-1
Bk2CP structure.png βk-2C-P2,5-dimethoxy-4-propylHHH
Bk2CiP structure.png βk-2C-iP2,5-dimethoxy-4-isopropylHHH1511033-62-7
BkDOB structure.png βk-DOB2,5-dimethoxy-4-bromoMeHH
BkMDOM structure.png βk-MDOM2,5-dimethoxy-4-methylMeHMe
MDC.png βk-MDA 3,4-methylenedioxyMeHH80535-73-5
BkMDAc structure.png N-Acetyl-βk-MDA3,4-methylenedioxyMeHacetyl
2,3-MDMC structure.png 2,3-MDMC2,3-methylenedioxyMeHMe1427205-87-5
Methylone.svg Methylone 3,4-methylenedioxyMeHMe186028-79-5
Dimethylone.svg Dimethylone 3,4-methylenedioxyMeMeMe109367-07-9
NAc-Methylone structure.png N-Acetylmethylone3,4-methylenedioxyMeacetylMe
NOH-Methylone structure.png N-Hydroxymethylone3,4-methylenedioxyMehydroxyMe
Bk-MDEA.svg Ethylone 3,4-methylenedioxyMeHEt1112937-64-0
Diethylone structure.png Diethylone3,4-methylenedioxyMeEtEt
NAc-Ethylone structure.png N-Acetylethylone3,4-methylenedioxyMeacetylEt
BkMDiP structure.png N-Isopropyl-βk-MDA3,4-methylenedioxyMeHiPr
BkMDtB structure.png MDPT3,4-methylenedioxyMeHt-Bu186028-84-2
BMDP structure.png Benzylone (BMDP)3,4-methylenedioxyMeHBn1823274-68-5
N-Cyclohexylmethylone structure.png N-Cyclohexylmethylone 3,4-methylenedioxyMeHcyclohexyl
3,4-EDMC structure.png 3,4-EDMC3,4-ethylenedioxyMeHMe30253-44-2
BkIMP structure.png βk-IMP3,4-trimethyleneMeHMe100608-69-3
BkIEB structure.png βk-IBP3,4-trimethyleneEtHEt
BkIEV structure.png βk-IVP3,4-trimethylenenPrHEt
3-fluorobuphedrone structure.png 3-Fluorobuphedrone3-FEtHMe
4-fluorobuphedrone structure.png 4-Fluorobuphedrone4-FEtHMe1368599-12-5
4-bromobuphedrone structure.png 4-Bromobuphedrone4-BrEtHMe
3-Methylbuphedrone structure.png 3-Methylbuphedrone3-MeEtHMe1797911-07-9
4-Methylbuphedrone.png 4-Me-MABP 4-MeEtHMe1336911-98-8
4-Me-NEB structure.png 4-Me-NEB4-MeEtHEt18268-19-4
2F-NEB structure.png 2-F-NEB2-FEtHEt
3F-NEB structure.png 3F-NEB 3-FEtHEt
4-F-NEB structure.png 4-F-NEB4-FEtHEt
4-Me-DMB structure.png 4-Me-DMB4-MeEtMeMe
3,4-DMEB structure.png 3,4-DMEB3,4-dimethylEtHEt
4-methoxybuphedrone structure.png 4-Methoxybuphedrone4-MeOEtHMe
Bk-MBDB.svg Butylone 3,4-methylenedioxyEtHMe802575-11-7
Eutylone.svg Eutylone 3,4-methylenedioxyEtHEt802855-66-9
BkPBDB structure.png βk-PBDB3,4-methylenedioxyEtHnPr
Bn-4-Me-MABP structure.png Bn-4-MeMABP4-MeEtHBn1445751-39-2
BMDB structure.png BMDB3,4-methylenedioxyEtHBn1445751-47-2
N-Cyclohexylbutylone structure.png N-Cyclohexylbutylone3,4-methylenedioxyEtHcyclohexyl
Dibutylone.svg βk-DMBDB 3,4-methylenedioxyEtMeMe802286-83-5
BkMMDMA structure.png βk-MMDMA 3,4-methylenedioxy-5-MeOMeHMe2230716-98-8
2-methoxymethylone structure.png βk-MMDMA-22-MeO-3,4-methylenedioxyMeHMe
BkDMMDA structure.png βk-DMMDA2,5-diMeO-3,4-methylenedioxyMeHH
5-methylmethylone structure.png 5-Methylmethylone3,4-methylenedioxy-5-MeMeHMe1364933-83-4
5-Methylethylone.svg 5-Methylethylone 3,4-methylenedioxy-5-MeMeHEt1364933-82-3
2-methylbutylone structure.png 2-Methylbutylone2-Me-3,4-methylenedioxyEtHMe1364933-86-7
5-methylbutylone structure.png 5-Methylbutylone3,4-methylenedioxy-5-MeEtHMe1354631-29-0
Pentylone.svg Pentylone 3,4-methylenedioxynPrHMe698963-77-8
N-Ethylpentylone.svg N-Ethylpentylone 3,4-methylenedioxynPrHEt727641-67-0
N-propylpentylone structure.png N-propylpentylone3,4-methylenedioxynPrHnPr
N-butylpentylone structure.png N-butylpentylone3,4-methylenedioxynPrHnBu
2,3-Dipentylone structure.png 2,3-Dipentylone2,3-methylenedioxynPrMeMe
Dipentylone.svg Dipentylone 3,4-methylenedioxynPrMeMe17763-13-2
NN-diethyl-pentylone structure.png N,N-Diethylnorpentylone3,4-methylenedioxynPrEtEt
Hexylone structure.png Hexylone3,4-methylenedioxynBuHMe
Isohexylone structure.png Isohexylone 3,4-methylenedioxyiBuHMe1157947-89-1
Isoheptylone structure.png Isoheptylone3,4-methylenedioxyiPeHMe
N-ethylhexylone structure.png N-Ethylhexylone 3,4-methylenedioxynBuHEt27912-41-0
N-ethylheptylone structure.png N-Ethylheptylone 3,4-methylenedioxynPeHEt
4-MEAP.svg 4-MEAP 4-MenPrHEt746540-82-9
3,4-DMEP structure.png 3,4-DMEP3,4-dimethylnPrHEt
2F-Pentedrone structure.png 2-F-Pentedrone2-FnPrHMe
3F-Pentedrone structure.png 3-F-Pentedrone3-FnPrHMe
4-fluoropentedrone structure.png 4-F-Pentedrone4-FnPrHMe
4-chloropentedrone structure.png 4-Cl-Pentedrone4-ClnPrHMe2167949-43-9
4-Methylpentedrone.png 4-Methylpentedrone 4-MenPrHMe1373918-61-6
DL-4662 structure.png DL-46623,4-dimethoxynPrHEt1674389-55-9
4F-NiP-pentedrone structure.png 4-F-iPr-norpentedrone4-FnPrHiPr
4Cl-NtB-pentedrone structure.png 3-CBV3-ClnPrHtBu
4-methylhexedrone structure.png 4-methylhexedrone4-MenBuHMe
4-methyl-N-ethylhexedrone structure.png MEH4-MenBuHEt
3F-NEH structure.png 3F-NEH 3-FnBuHEt
4-fluorohexedrone structure.png 4-F-hexedrone4-FnBuHMe
4-fluorooctedrone structure.png 4-F-octedrone4-FhexylHMe
Alpha-phenylmephedrone structure.png α-phenylmephedrone4-MephenylHMe
Bk-EPE structure.png βk-Ephenidine HphenylHEt22312-16-9
Bk-methamnetamine.svg BMAPN β-naphthyl instead of phenylMeHMe
Thiothinone.svg βk-Methiopropamine thiophen-2-yl instead of phenylMeHMe24065-17-6
5ClbkMPA structure.png 5-Cl-bk-MPA 5-chlorothiophen-2-yl instead of phenylMeHMe
Bk-5-MAPB structure.png βk-5-MAPB benzofuran-5-yl instead of phenylMeHMe
Bk-6-MAPB structure.png βk-6-MAPBbenzofuran-6-yl instead of phenylMeHMe
Bk-5-IT structure.png βk-5-ITindol-5-yl instead of phenylMeHH1369231-36-6
BK-5F-NM-AMT structure.png βk-5F-NM-AMT [38] 5-fluoroindol-3-yl instead of phenylMeHMe
Phthalprop.svg α-Phthalimidopropiophenone HMephthalimido19437-20-8
PPPO structure.png PPPOHMepiperidinyl
PPBO structure.png PPBOHEtpiperidinyl92728-82-0
FPPVO structure.png FPPVO4-FnPrpiperidinyl
3,4-Pr-PipVP structure.png 3,4-Pr-PipVP 3,4-trimethylenenPrpiperidinyl
MDPV-azepane structure.png MDPV-azepane3,4-methylenedioxynPr azepane
Caccure907 structure.png Caccure 9074-SCH3α,α-di-Memorpholinyl
A-PPP.svg α-PPP HMepyrrolidinyl19134-50-0
A-PBP.svg α-PBP HEtpyrrolidinyl13415-54-8
Alpha-Pyrrolidinopentiophenone.svg α-PVP (O-2387)HnPrpyrrolidinyl14530-33-7
A-PHP.svg α-PHP H nBu pyrrolidinyl13415-86-6
Alpha-PHiP structure.png α-PHiP HiBupyrrolidinyl
Alpha-Pyrrolidinoheptaphenone.svg α-PEP (α-PHPP)H nPe pyrrolidinyl13415-83-3
Alpha-POP structure.png α-POPH hexyl pyrrolidinyl
Alpha-PNP structure.png α-PNPH heptyl pyrrolidinyl
Diphenylpyrrolidinylethanone structure.png DPPE (Alpha-D2PV)Hphenylpyrrolidinyl27590-61-0
Alpha-PcPeP structure.png α-PcPePH cyclopentyl pyrrolidinyl
Alpha-PCYP structure.png α-PCYP H cyclohexyl pyrrolidinyl1803168-11-7
2-Me-PPP structure.png 2-MePPP2-MeMepyrrolidinyl2092429-83-7
3-Me-PPP structure.png 3-MePPP3-MeMepyrrolidinyl1214940-01-8
PMPPP.svg 4-MePPP 4-MeMepyrrolidinyl1313393-58-6
3MeO-PPP structure.png 3-MeO-PPP3-MeOMepyrrolidinyl
MOPPP SVG.svg MOPPP 4-MeOMepyrrolidinyl478243-09-3
3-F-PPP structure.png 3-F-PPP3-FMepyrrolidinyl1214939-99-7
4-F-PPP structure.png FPPP4-FMepyrrolidinyl28117-76-2
4-Cl-PPP structure.png Cl-PPP4-ClMepyrrolidinyl93307-24-5
3-Br-PPP structure.png 3-Br-PPP3-BrMepyrrolidinyl
4Br-PPP structure.png Br-PPP4-BrMepyrrolidinyl
2,3-DMPPP structure.png 2,3-DMPPP2,3-dimethylMepyrrolidinyl
2,4-DMPPP structure.png 2,4-DMPPP2,4-dimethylMepyrrolidinyl
3,4-DMPPP structure.png 3,4-DMPPP3,4-dimethylMepyrrolidinyl
3-Me-PBP structure.png 3-MPBP3-MeEtpyrrolidinyl1373918-60-5
3-F-PBP structure.png 3-F-PBP3-FEtpyrrolidinyl1373918-59-2
MPBP.svg MPBP 4-MeEtpyrrolidinyl732180-91-5
4-F-PBP structure.png FPBP4-FEtpyrrolidinyl1373918-67-2
4-Et-PBP structure.png EPBP4-EtEtpyrrolidinyl
4-MeO-PBP structure.png MOPBP4-MeOEtpyrrolidinyl
MMOPBP structure.png MMOPBP3-Me-4-MeOEtpyrrolidinyl
O-2384 structure.png O-23843,4-dichloroEtpyrrolidinyl850352-65-7
2Me-PVP structure.png 2-Me-PVP 2-MenPrpyrrolidinyl850352-54-4
3Me-PVP structure.png 3-Me-PVP 3-MenPrpyrrolidinyl13415-85-5
Pyrovalerone.svg Pyrovalerone (O-2371)4-MenPrpyrrolidinyl3563-49-3
4-Et-PVP structure.png 4-Et-PVP 4-EtnPrpyrrolidinyl
3-F-PVP structure.png 3F-PVP 3-FnPrpyrrolidinyl2725852-55-9
FPVP.svg FPVP 4-FnPrpyrrolidinyl850352-31-7
2Cl-PVP structure.png 2-Cl-PVP2-ClnPrpyrrolidinyl
3Cl-PVP structure.png 3-Cl-PVP3-ClnPrpyrrolidinyl
4-Cl-PVP structure.png 4-Cl-PVP 4-ClnPrpyrrolidinyl5537-17-7
3-Br-PVP structure.png 3-Br-PVP3-BrnPrpyrrolidinyl
4-Br-PVP structure.png 4-Br-PVP4-BrnPrpyrrolidinyl
MOPVP.svg MOPVP 4-MeOnPrpyrrolidinyl5537-19-9
DMPVP.svg DMOPVP 3,4-dimethoxynPrpyrrolidinyl850442-84-1
3,4-DMPVP structure.png DMPVP3,4-dimethylnPrpyrrolidinyl
O-2390 structure.png O-2390 3,4-dichloronPrpyrrolidinyl850352-61-3
MFPVP structure.png MFPVP 3-methyl-4-fluoronPrpyrrolidinyl
MPHP.svg MPHP 4-MenBupyrrolidinyl34138-58-4
3F-PHP structure.png 3F-PHP 3-FnBupyrrolidinyl
4-F-PHP structure.png 4F-PHP 4-FnBupyrrolidinyl2230706-09-7
4-Cl-PHP structure.png 4-Cl-PHP 4-ClnBupyrrolidinyl2748592-29-0
DMOPHP structure.png DMOPHP3,4-dimethoxynBupyrrolidinyl
MFPHP structure.png MFPHP3-Me-4-FnBupyrrolidinyl
3-F-PiHP structure.png 3F-PiHP 3-FiBupyrrolidinyl
4-F-PiHP structure.png 4F-PiHP4-FiBupyrrolidinyl
O-2494 structure.png O-23944-Me iBu pyrrolidinyl850352-51-1
4-Me-PEP structure.png MPEP4-Me pentyl pyrrolidinyl
4-F-PEP structure.png 4F-PV84-Fpentylpyrrolidinyl
4-MeO-PEP structure.png 4-MeO-PV84-MeOpentylpyrrolidinyl
MFPEP structure.png MFPEP3-Me-4-Fpentylpyrrolidinyl
MCPEP structure.png MCPEP3-Me-4-Clpentylpyrrolidinyl
FPOP.svg 4F-PV9 4-F hexyl pyrrolidinyl
4-MeO-POP structure.png 4-MeO-PV94-MeOhexylpyrrolidinyl
Alpha-phenylpyrovalerone structure.png α-Phenylpyrovalerone4-Me phenyl pyrrolidinyl
MDPPP.svg MDPPP 3,4-methylenedioxyMepyrrolidinyl783241-66-7
MDMPP structure.png MDMPP3,4-methylenedioxyα,α-di-Mepyrrolidinyl
3',4'-Methylenedioxy-a-pyrrolidinobutiophenone.svg MDPBP 3,4-methylenedioxyEtpyrrolidinyl784985-33-7
MDPV.svg MDPV 3,4-methylenedioxynPrpyrrolidinyl687603-66-3
2,3-MDPV structure.png 2,3-MDPV2,3-methylenedioxynPrpyrrolidinyl
5-Me-MDPV structure.png 5-Me-MDPV3,4-methylenedioxy-5-MenPrpyrrolidinyl
6-Me-MDPV structure.png 6-Me-MDPV2-Me-4,5-methylenedioxynPrpyrrolidinyl
6-MeO-MDPV structure.png 6-MeO-MDPV2-MeO-4,5-methylenedioxynPrpyrrolidinyl
4-MeO-5-Br-2,3-MDPV structure.png Br-MeO-MDPV2,3-methylenedioxy-4-MeO-5-BrnPrpyrrolidinyl
MDPiVP structure.png MDPiVP3,4-methylenedioxyiPrpyrrolidinyl
MDPHP.svg MDPHP 3,4-methylenedioxynBupyrrolidinyl776994-64-0
MDPHiP structure.png MDPHiP3,4-methylenedioxyiBupyrrolidinyl
MDPEP structure.png MDPEP (MD-PV8)3,4-methylenedioxypentylpyrrolidinyl24646-39-7
MDPOP structure.png MDPOP (MD-PV9)3,4-methylenedioxyhexylpyrrolidinyl24646-40-0
3,4-EtPV structure.png 3,4-EtPV3,4-dimethylenenPrpyrrolidinyl
5-PPDI structure.png 5-PPDi3,4-trimethyleneEtpyrrolidinyl
5-BPDI structure.png Indanyl-α-PVP3,4-trimethylenenPrpyrrolidinyl2748590-83-0
5-HPDI structure.png 5-BPDi 3,4-trimethylenenBupyrrolidinyl
Indapyrophenidone.svg IPPV 3,4-trimethylenephenylpyrrolidinyl
TH-PBP structure.png TH-PBP3,4-tetramethyleneEtpyrrolidinyl
TH-PVP structure.png TH-PVP 3,4-tetramethylenenPrpyrrolidinyl2304915-07-7
TH-PHP structure.png TH-PHP3,4-tetramethylenenBupyrrolidinyl
5-DBFPV.svg 5-DBFPV 2,3-dihydrobenzofuran-5-yl instead of PhnPrpyrrolidinyl1620807-94-4
3-BF-PVP structure.png 3-BF-PVPbenzofuran-3-yl instead of PhnPrpyrrolidinyl
Naphyrone.svg Naphyrone (O-2482)β-naphthyl instead of phenylnPrpyrrolidinyl850352-53-3
Alpha-naphyrone structure.png α-Naphyroneα-naphthyl instead of phenylnPrpyrrolidinyl
Alpha-PPT structure.png α-PPTthiophen-2-yl instead of phenylMepyrrolidinyl
Alpha-PBT structure.png α-PBTthiophen-2-yl instead of phenylEtpyrrolidinyl
A-PVT.svg α-PVT thiophen-2-yl instead of phenylnPrpyrrolidinyl1400742-66-6

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. [39]

"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. [40] 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, [41] [42] along with a further broad based structure ban even more expansive than the last. [43] [44]

"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 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:

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. [45]

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. [46]

See also

Related Research Articles

<span class="mw-page-title-main">Misuse of Drugs Act 1971</span> United Kingdom legislation

The Misuse of Drugs Act 1971 is an act of the Parliament of the United Kingdom. It represents action in line with treaty commitments under the Single Convention on Narcotic Drugs, the Convention on Psychotropic Substances, and the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.

<span class="mw-page-title-main">Methylone</span> Group of stereoisomers

Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.

α-Pyrrolidinopropiophenone Chemical compound

α-Pyrrolidinopropiophenone (α-PPP), is a stimulant drug. It is similar in structure to the appetite suppressant diethylpropion and has analogous effects in animals. Little is known about this compound, but it has been detected by laboratories in Germany as an ingredient in "ecstasy" tablets seized by law enforcement authorities. This drug has been found to produce stimulant effects in animals and produces highly stimulating effects in humans, based on the experiences of the individuals who have tried it. Most of the individuals who have tried it prefer α-PVP to it, but prefer this drug over α-PVT. It is said to lack euphoria compared to α-PVP.

<span class="mw-page-title-main">MDAI</span> Chemical compound

MDAI, also known as 5,6-methylenedioxy-2-aminoindane, is an entactogen drug of the 2-aminoindane group which is related to MDMA and produces similar subjective effects.

<span class="mw-page-title-main">2-Aminoindane</span> Chemical compound

2-Aminoindane (2-AI) is an aminoindane and research chemical with applications in neurologic disorders and psychotherapy that has also been sold as a designer drug. It acts as a selective substrate for NET and DAT.

<span class="mw-page-title-main">Substituted phenethylamine</span> Chemical class of organic compounds

Substituted phenethylamines are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents.

α-Pyrrolidinopentiophenone Chemical compound

α-Pyrrolidinopentiophenone (α-PVP), also known as α-pyrrolidinovalerophenone, O-2387, β-keto-prolintane, prolintanone, or desmethylpyrovalerone, is a synthetic stimulant of the cathinone class developed in the 1960s that has been sold as a designer drug and often consumed for recreational reasons. α-PVP is chemically related to pyrovalerone and is the ketone analog of prolintane.

<span class="mw-page-title-main">3-Fluoroamphetamine</span> Stimulant drug that acts as an amphetamine

3-Fluoroamphetamine is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin. It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine.

<span class="mw-page-title-main">Cannabicyclohexanol</span> Chemical compound

Cannabicyclohexanol is a cannabinoid receptor agonist drug, developed by Pfizer in 1979. On 19 January 2009, the University of Freiburg in Germany announced that an analog of CP 47,497 was the main active ingredient in the herbal incense product Spice, specifically the 1,1-dimethyloctyl homologue of CP 47,497, which is now known as cannabicyclohexanol. The 1,1-dimethyloctyl homologue of CP 47,497 is in fact several times more potent than the parent compound, which is somewhat unexpected as the 1,1-dimethylheptyl is the most potent substituent in classical cannabinoid compounds such as HU-210.

<span class="mw-page-title-main">6-(2-Aminopropyl)indole</span> Chemical compound

6-(2-Aminopropyl)indole is an indole derivative which was first identified being sold on the designer drug market by a laboratory in the Czechia in July 2016.

<span class="mw-page-title-main">Substituted phenylmorpholine</span> Class of chemical compounds

Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of phenylmorpholine or of the psychostimulant drug phenmetrazine. Most such compounds act as releasers of monoamine neurotransmitters, and have stimulant effects. Some also act as agonists at serotonin receptors, and compounds with an N-propyl substitution act as dopamine receptor agonists. A number of derivatives from this class have been investigated for medical applications, such as for use as anorectics or medications for the treatment of ADHD. Some compounds have also become subject to illicit use as designer drugs.

<span class="mw-page-title-main">Substituted benzofuran</span> Class of chemical compounds

The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Many medicines use the benzofuran core as a scaffold, but most commonly the term is used to refer to the simpler compounds in this class which include numerous psychoactive drugs, including stimulants, psychedelics and empathogens. In general, these compounds have a benzofuran core to which a 2-aminoethyl group is attached, and combined with a range of other substituents. Some psychoactive derivatives from this family have been sold under the name Benzofury.

<i>N</i>-Ethylhexedrone Stimulant of the cathinone class

N-Ethylhexedrone (also known as α-ethylaminocaprophenone, N-ethylnorhexedrone, hexen, and NEH) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) with IC50 values of 0.0978 and 0.0467 μM, respectively. N-Ethylhexedrone was first mentioned in a series of patents by Boehringer Ingelheim in the 1960s which led to the development of the better-known drug methylenedioxypyrovalerone (MDPV). Since the mid-2010s, N-ethylhexedrone has been sold online as a designer drug. In 2018, N-ethylhexedrone was the second most common drug of the cathinone class to be identified in Drug Enforcement Administration seizures.

<span class="mw-page-title-main">5-MBPB</span> Chemical compound

5-MBPB is an amphetamine derivative which is structurally related to MDMA and has been sold as a designer drug. It can be described as the benzofuran-5-yl analogue of MBDB or the butanamine homologue of 5-MAPB, and is also a structural isomer of 5-EAPB and 6-EAPB. Anecdotal reports suggest this compound has been sold as a designer drug in various European countries since early 2015, but the first definitive identification was made in December 2015 by a forensic laboratory in Slovenia.

α-PHiP Stimulant drug

α-Pyrrolidinoisohexanophenone is a stimulant drug of the cathinone class that has been sold online as a designer drug. It acts as a potent norepinephrine-dopamine reuptake inhibitor (NDRI). In July 2016 α-PHiP was first identified as a designer drug when it was reported to the EMCDDA by a forensic laboratory in Slovenia. It is a positional isomer of pyrovalerone, with the methyl group shifted from the 4-position of the aromatic ring to the 4-position of the acyl chain. Similarly to other cathinones, use of α-PiHP can result in compulsive redosing, addiction, anxiety, paranoia, and psychosis.

<span class="mw-page-title-main">TH-PVP</span> Chemical compound

TH-PVP is a substituted cathinone derivative which has been sold as a designer drug. It was first identified by a forensic laboratory in Hungary in 2015, but has subsequently been found in numerous other countries around the world including Spain, Belgium, Poland, Turkey and Brazil. Pharmacological studies in vitro showed it to inhibit reuptake and promote the release of monoamine neurotransmitters with some selectivity for serotonin, but it failed to produce stimulant effects in animals, and has a pharmacological profile more comparable to that of sedating empathogens such as MDAI and 5-Methyl-MDA.

<span class="mw-page-title-main">4-Methylphenmetrazine</span> Stimulant designer drug

4-Methylphenmetrazine is a recreational designer drug with stimulant effects. It is a substituted phenylmorpholine derivative, closely related to better known drugs such as phenmetrazine and 3-fluorophenmetrazine. It was first identified in Slovenia in 2015, and has been shown to act as a monoamine releaser with some preference for serotonin release.

<span class="mw-page-title-main">Butylamphetamine</span> Amphetamine derivative and stimulant

Butylamphetamine (code name PAL-90; also known as N-butylamphetamine or NBA) is a psychostimulant of the substituted amphetamine family which was never marketed. It is the N-butyl analogue of amphetamine and is approximately 6-fold less potent than amphetamine in rats. The drug has been found to be inactive as a dopamine reuptake inhibitor or releasing agent (IC50Tooltip half-maximal inhibitory concentration and EC50Tooltip half-maximal effective concentration > 10,000 nM, respectively). With regard to structure–activity relationships, the potency of N-substituted amphetamine derivatives decreases with increasing chain length in terms of both in vitro and in vivo activity. The pharmacokinetics of butylamphetamine have been studied in humans. It can be metabolized by CYP2D6 via ring hydroxylation similarly to amphetamine.

<span class="mw-page-title-main">Substituted β-hydroxyamphetamine</span> Class of compounds based upon the β-hydroxyamphetamine structure

Substituted β-hydroxyamphetamines, or simply β-hydroxyamphetamines, also known as substituted phenylisopropanolamines, substituted phenylpropanolamines, substituted norephedrines, or substituted cathinols, are derivatives of β-hydroxyamphetamine with one or more chemical substituents. They are substituted phenethylamines, phenylethanolamines (β-hydroxyphenethylamines), and amphetamines (α-methylphenethylamines), and are closely related to but distinct from the substituted cathinones (β-ketoamphetamines). Examples of β-hydroxyamphetamines include the β-hydroxyamphetamine stereoisomers phenylpropanolamine and cathine and the stereospecific N-methylated β-hydroxyamphetamine derivatives ephedrine and pseudoephedrine, among many others.

<span class="mw-page-title-main">4-Fluoroephedrine</span> An analogue of ephedrine and a norepinephrine releasing agent

4-Fluoroephedrine (4-FEP) is a "novel psychoactive substance" and substituted β-hydroxyamphetamine derivative related to ephedrine.

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