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, 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]

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, most 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] In addition, β-keto-substituted phenethylamines, such as βk-2C-B, appear to show dramatically reduced potency and efficacy as serotonin 5-HT2A receptor agonists compared to their non-β-keto-substituted counterparts.[16]

Monoamine release profiles

The following is a list of serotonin, dopamine, and norepinephrine releasing profiles for various cathinones, measured in rat brain synaptosomes.[7][8][17]

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Monoamine release profiles of cathinones in rat brain synaptosomes (EC50, nM)[7][8][17]
Name PAL # Serotonin Norepinephrine Dopamine Type References
2-BMC ND 2837 156 650 NDRA [18]
2-CMC ND 2815 93 179 NDRA [18]
2-FMC ND >10000 ND
(85% at 10 μM)		 48.7 NDRA [19]
2-MeO-MC ND 7220 339 920 NDRA [18]
2-MMC ND 347–490 53 81–97.9 SNDRA [19][18]
2-TFMeO-MC ND >10000 ND
(33% at 10 μM)		 >10000 IA [19]
2-TFMMC (2-TFMAP) ND 8400–>10000 2200
(69% at 10 μM)		 8000–>10000 SNDRA [20][19][21][18]
3-BCPC PAL-586 621 ND IA (RI) ND [22][23]
3-BMC ND 136–137 25 21–28.0 SNDRA [19][24][18]
3-CC ND 567 105 64 SNDRA [25][24]
3-CCPC (RTI-6037-39) PAL-433 1328 ND IA (RI) ND [22][26]
  (–)-3-CCPC PAL-1122 562 ND IA (RI) ND [22]
  (+)-3-CCPC PAL-1123 733 ND IA (RI) ND [22]
3-CEC PAL-361 IA ND IA ND [22]
3-Cl-4-Me-CPC PAL-820 181 ND IA (RI) ND [22]
3-CMC (clophedrone) PAL-434 211–410 19–54.4 26–46.8 SNDRA [9][19][24][18][22][27]
3-CPC PAL-363 IA ND IA (RI) ND [22]
3-FMC ND 1460 ND
(100% at 10 μM)		 64.8 NDRA [19]
3-MCPC PAL-588 1067 ND IA (RI) ND [22]
3-MeO-CPC PAL-591 1014 ND IA (RI) ND [22]
3-MeO-MC ND 306–683 111
(68% at 10 μM)		 109–129 SNDRA [19][28][29][24][18]
3-MMC ND 268–292 27 28–70.6 SNDRA [9][19][24][18]
3-TFMeO-MC ND 188 ND
(79% at 10 μM)		 729 SNDRA [19]
3-TFMMC (3-TFMAP) ND 297–380 2700
(78% at 10 μM)		 610–1290 SNDRA [20][19][21][18]
3,4-DCCPC PAL-787 356 ND IA (RI) ND [22]
4-BMC (brephedrone) ND 42.5–60.2 100 59.4 SNDRA [30][19][24][18][31][32]
4-CC ND 128.4 85.1 221.8 SNDRA [33][34]
4-CCPC PAL-743 1632 ND IA (RI) ND [22]
4-CEC ND 152.6 5194.0 353.6 SDRA [33]
4-CMC (clephedrone) ND 71.1–144 44–90.9 42.2–74.7 SNDRA [30][19][33][24][18][31][32]
4-FMC (flephedrone) ND 1290–1450 62 83.4–119 NDRA [30][19][24][31][32]
4-MCPC PAL-744 667 ND IA (RI) ND [22]
4-MeO-MC (methedrone) ND 120–195 111 506–881 SNDRA [30][19][24][18][31][32]
4-TFMeO-MC ND 118 ND 7510 ND [19]
4-TFMMC (4-TFMAP) ND 190–270 900 2700–4230 SNRA [35][30][20][21][32][18]
α-Me-MC (βk-mephentermine; RAD-081) ND 12860 153 590 NDRA [36][37][38]
AMAPN ND 21 ND 55 ND [19][28]
Amfepramone (diethylpropion) ND >10000 >10000 >10000 PD [39][40]
BMAPN ND 27 ND 34 ND [19][28]
Buphedrone (βk-MEPEA) PAL-429 IA ND 411 ND [22]
Bupropion (amfebutamone) ND IA (RI) IA (RI) IA (RI) NDRI [38][25][24]
Butylone (βk-MBDB) ND 330 IA (RI) IA (RI) SRA/NDRI [41][42]
Cathinone (C; βk-AMPH) ND 6100–7595 23.6–25.6 34.8–83.1 NDRA [17][43][19][33]
  D-Cathinone ND >10000 72.0 183.9 NDRA [44]
  L-Cathinone ND 2366–9267 12.4–28 18–24.6 NDRA [45][25][44]
Dibutylone ND IA IA (RI) IA (RI) DRI [46]
EDMC ND 347 327 496 SNDRA [47][31]
Ephylone ND IA (RI) IA (RI) IA (RI) IA (NDRI) [48]
Ethcathinone (EC) ND 1923–2118 88.3–99.3 267.6–>1000 NRA [39][17][33][49]
Ethylone (βk-MDEA) ND 617.4 4251 1122 SNDRA [31]
Eutylone (βk-EBDB) ND 1020 IA (RI) IA (RI) SRA/NDRI [46]
HHMC ND 14100 110 90 NDRA [50]
HDMI ND 7210 6340 5840 SNDRA [50]
MDC ND 966 394 370 SNDRA [50]
Mephedrone (4-MMC) ND 118.3–122 58–62.7 49.1–51 SNDRA [12][51][19][18][32]
  S(–)-Mephedrone ND 61 ND 74 ND [49][52]
  R(+)-Mephedrone ND 1470 ND 31 ND [49][52]
Methcathinone (MC) ND 2592–5853 22–26.1 12.5–49.9 NDRA [17][19][24][18][33]
  D-Methcathinone ND IA ND ND NRA [38]
  L-Methcathinone ND 1772 13.1 14.8 NDRA [49]
Methylone (MDMC) ND 234–708 140–270 117–220 SNDRA [12][51][31][46][50]
Mexedrone (4-MMC-MeO) ND 2525 IA (RI) IA (RI) SRA/NDRI [53]
Normephedrone (4-MC) ND 210 100 220 SNDRA [54][44][49]
  R(+)-Normephedrone ND 179 89 150 SNDRA [49][44]
  S(–)-Normephedrone ND 1592 115 391 NDRA [49][44]
Pentylone ND 476–1030
(Emax ≈ 50%)		 IA (RI) IA (RI) SRA/NDRI [41][46][48]
Propylone ND 3128 IA (RI) 975.9 SDRA [31]

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:[55][56][57][58][59][60][61][62][63][64][65][66][67][68][69][70][71][72][73][74][75][76]

Template:Sticky

Structure Compound R1 R2 R3 R4 CAS #
Cathinone H Me H H 71031-15-7
File:Methcathinone structure.svg Methcathinone H Me H Me 5650-44-2
File:Ethcathinone structure.svg Ethcathinone H Me H Et 51553-17-4
Error creating thumbnail: Propylcathinone H Me H nPr 52597-14-5
File:Buphedrone structure.svg Buphedrone H Et H Me 408332-79-6
N-Ethylbuphedrone (NEB) H Et H Et 1354631-28-9
File:Methylethylbuphedrone structure.png N-Methyl-N-ethylbuphedrone H Et Me Et
Pentedrone H nPr H Me 879722-57-3
File:N-Ethylpentedrone structure.png N-Ethylpentedrone H nPr H Et 18268-16-1
File:N-Isopropylpentedrone structure.png 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
File:Butylhexedrone structure.png N-Butylhexedrone H nBu H nBu 18296-66-7
File:Isobutylhexedrone structure.png N-Isobutylhexedrone (NDH) H nBu H i-Bu
File:Isohexedrone structure.png Isohexedrone H iBu H Me
N-Ethylheptedrone H nPe H Et
File:Octedrone structure.png Octedrone H hexyl H Me
File:Metamfepramone.svg Dimethylcathinone H Me Me Me 15351-09-4
File:Amfepramone structure.svg Diethylpropion H Me Et Et 134-80-5
File:NN-methylethylcathinone structure.png N-Methyl-N-ethylcathinone H Me Me Et 1157739-24-6
File:Bupropion structure.svg Bupropion 3-Cl Me H t-Bu 34911-55-2
File:Hydroxybupropion structure.svg Hydroxybupropion 3-Cl Me H 2-Me-3-OH-propan-2-yl 357399-43-0
File:Mephedrone structure.svg Mephedrone 4-Me Me H Me 1189805-46-6
File:2-Methylmethcathinone.svg 2-MMC 2-Me Me H Me 1246911-71-6
File:2-MEC structure.png 2-MEC 2-Me Me H Et 1439439-84-5
File:2-EMC structure.png 2-EMC 2-Et Me H Me
File:2-EEC structure.png 2-EEC 2-Et Me H Et 2446466-59-5
File:Metaphedrone.svg 3-MMC 3-Me Me H Me 1246816-62-5
File:3-MEC structure.png 3-MEC 3-Me Me H Et 1439439-83-4
File:3-MPC structure.png 3-MPC 3-Me Me H nPr
Error creating thumbnail: 3-EMC 3-Et Me H Me
File:3-EEC structure.png 3-EEC 3-Et Me H Et 2446466-61-9
4-EMC 4-Et Me H Me 1225622-14-9
File:4-EEC structure.png 4-EEC 4-Et Me H Et 2446466-62-0
File:4-Methylcathinone.svg 4-MC 4-Me Me H H 31952-47-3
Benzedrone 4-Me Me H Bn 1225617-75-3
File:2'-MeO-benzedrone structure.png 2'-MeO-Benzedrone 4-Me Me H 2-MeO-Bn
File:2,N-DM-Benzedrone structure.png 2,N-Dimethylbenzedrone 2-Me Me Me Bn
File:3,N-DM-Benzedrone structure.png 3,N-Dimethylbenzedrone 3-Me Me Me Bn
File:4,N-DM-Benzedrone structure.png 4,N-Dimethylbenzedrone 4-Me Me Me Bn
4-MEC 4-Me Me H Et 1225617-18-4
File:4-methyl-propylcathinone structure.png 4-MPC 4-Me Me H nPr
File:NN-DMMC structure.png N,N-DMMC 4-Me Me Me Me 1448845-14-4
File:NN-MEMC structure.png N,N-MEMC 4-Me Me Me Et
File:NN-DEMC structure.png N,N-DEMC 4-Me Me Et Et 676316-90-8
4-MEAP 4-Me Pr H Et 746540-82-9
File:4-EDMC structure.png EDMC 4-Et Me Me Me
File:2,3-DMMC structure.png 2,3-DMMC 2,3-dimethyl Me H Me
File:2,3-DMEC structure.png 2,3-DMEC 2,3-dimethyl Me H Et
File:2,4-DMMC structure.png 2,4-DMMC 2,4-dimethyl Me H Me 1225623-63-1
File:2,4-DMEC structure.png 2,4-DMEC 2,4-dimethyl Me H Et 1225913-88-1
File:2,5-DMMC structure.png 2,5-DMMC 2,5-dimethyl Me H Me
File:2,5-DMEC structure.png 2,5-DMEC 2,5-dimethyl Me H Et
File:2,6-DMMC structure.png 2,6-DMMC 2,6-dimethyl Me H Me
File:2,6-DMEC structure.png 2,6-DMEC 2,6-dimethyl Me H Et
3,4-DMMC 3,4-dimethyl Me H Me 1082110-00-6
File:3,4-DMEC structure.png 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-Fluoromethcathinone.svg 2-FMC 2-F Me H Me 1186137-35-8
File:2-FEC structure.png 2-FEC 2-F Me H Et
File:3-Fluoromethcathinone.svg 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
File:3-Chloromethcathinone.svg Clophedrone (3-CMC) 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
File:Flephedrone.svg Flephedrone 4-F Me H Me 447-40-5
4-FEC 4-F Me H Et 1225625-74-0
File:4-Chloromethcathinone.svg Clephedrone (4-CMC) 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
File:4-Bromomethcathinone.svg 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
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
File:Methylenedioxycathinone.svg 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
File:Ethylone.svg 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
File:3-Methylbuphedrone structure.png 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
Error creating thumbnail: 3,4-DMEB 3,4-dimethyl Et H Et
File:4-methoxybuphedrone structure.png 4-Methoxybuphedrone 4-MeO Et H Me
File:Butylone.svg Butylone 3,4-methylenedioxy Et H Me 802575-11-7
File:Eutylone structure.svg 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
File:5-Methoxymethylone.svg 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
File:5-Methylethylone structure.svg 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
File:Pentylone structure.svg 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
File:Isohexylone.svg 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
File:4-Methylpentedrone.svg 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
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
File:Thiothinone structure.svg βk-Methiopropamine thiophen-2-yl instead of phenyl Me H Me 24065-17-6
5-Cl-bk-MPA 5-chlorothiophen-2-yl instead of phenyl Me H Me
File:BK-5-MAPB.svg βk-5-MAPB benzofuran-5-yl instead of phenyl Me H Me
File:BK-6-MAPB.svg 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
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:3,4-Pr-PipVP structure.png 3,4-Pr-PipVP 3,4-trimethylene 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
File:Α-PHiP.svg 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 (Alpha-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 850352-54-4
File:3Me-PVP structure.png 3-Me-PVP 3-Me nPr pyrrolidinyl 13415-85-5
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 2725852-55-9
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
3F-PiHP 3-F iBu pyrrolidinyl
File:4-F-PiHP structure.png 4F-PiHP 4-F iBu pyrrolidinyl
File:O-2494 structure.png O-2494 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:3,4-EtPV structure.png 3,4-EtPV 3,4-dimethylene nPr pyrrolidinyl
File:5-PPDI structure.png 5-PPDi 3,4-trimethylene Et pyrrolidinyl
File:5-BPDI structure.png Indanyl-α-PVP 3,4-trimethylene nPr pyrrolidinyl 2748590-83-0
File:5-HPDI structure.png 5-BPDi 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
File:Α-PVT structure.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.[77]

"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.[78] 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,[79][80] along with a further broad based structure ban even more expansive than the last.[81][82]

"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.[83]

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.[84]

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). 2011. doi:10.1371/journal.pone.0020602. PMID 21698275. Bibcode: 2011PLoSO...620602C. 
  7. ↑ 7.0 7.1 7.2 "Monoamine transporters and psychostimulant drugs". Eur. J. Pharmacol. 479 (1–3): 23–40. 2003. doi:10.1016/j.ejphar.2003.08.054. PMID 14612135. 
  8. ↑ 8.0 8.1 8.2 "Therapeutic potential of monoamine transporter substrates". Curr Top Med Chem 6 (17): 1845–1859. 2006. doi:10.2174/156802606778249766. PMID 17017961. 
  9. ↑ 9.0 9.1 9.2 "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug and Alcohol Dependence 147: 1–19. February 2015. doi:10.1016/j.drugalcdep.2014.12.005. PMID 25548026. 
  10. ↑ "Targeted screening for biogenic amine transporters: potential applications for natural products". Life Sciences 78 (5): 512–518. December 2005. doi:10.1016/j.lfs.2005.09.001. PMID 16202429. 
  11. ↑ "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse 39 (1): 32–41. January 2001. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707. 
  12. ↑ 12.0 12.1 12.2 "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology 37 (5): 1192–203. April 2012. doi:10.1038/npp.2011.304. PMID 22169943. 
  13. ↑ 13.0 13.1 "A narrative review of the neuropharmacology of synthetic cathinones-Popular alternatives to classical drugs of abuse". Hum Psychopharmacol 38 (3). May 2023. doi:10.1002/hup.2866. PMID 36866677. "Another feature that distinguishes [substituted cathinones (SCs)] from amphetamines is their negligible interaction with the trace amine associated receptor 1 (TAAR1). Activation of this receptor reduces the activity of dopaminergic neurones, thereby reducing psychostimulatory effects and addictive potential (Miller, 2011; Simmler et al., 2016). Amphetamines are potent agonists of this receptor, making them likely to self‐inhibit their stimulating effects. In contrast, SCs show negligible activity towards TAAR1 (Kolaczynska et al., 2021; Rickli et al., 2015; Simmler et al., 2014, 2016). [...] The lack of self‐regulation by TAAR1 may partly explain the higher addictive potential of SCs compared to amphetamines (Miller, 2011; Simmler et al., 2013).". 
  14. ↑ 14.0 14.1 "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther 357 (1): 134–144. April 2016. doi:10.1124/jpet.115.229765. PMID 26791601. https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA. Retrieved 9 May 2025. 
  15. ↑ "Monoamine transporter and receptor interaction profiles of a new series of designer cathinones". Neuropharmacology 79: 152–160. April 2014. doi:10.1016/j.neuropharm.2013.11.008. PMID 24275046. 
  16. ↑ "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor". Arch Toxicol 94 (10): 3449–3460. October 2020. doi:10.1007/s00204-020-02836-w. PMID 32627074. Bibcode: 2020ArTox..94.3449P. 
  17. ↑ 17.0 17.1 17.2 17.3 17.4 "Dopamine-releasing agents". Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. July 2008. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf. 
  18. ↑ 18.00 18.01 18.02 18.03 18.04 18.05 18.06 18.07 18.08 18.09 18.10 18.11 18.12 18.13 18.14 18.15 "Systematic Structure-Activity Studies on Selected 2-, 3-, and 4-Monosubstituted Synthetic Methcathinone Analogs as Monoamine Transporter Releasing Agents". ACS Chem Neurosci 10 (1): 740–745. January 2019. doi:10.1021/acschemneuro.8b00524. PMID 30354055. 
  19. ↑ 19.00 19.01 19.02 19.03 19.04 19.05 19.06 19.07 19.08 19.09 19.10 19.11 19.12 19.13 19.14 19.15 19.16 19.17 19.18 19.19 19.20 "The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes". Psychopharmacology 236 (3): 915–924. March 2019. doi:10.1007/s00213-018-5063-9. PMID 30341459. 
  20. ↑ 20.0 20.1 20.2 "Pharmacological examination of trifluoromethyl ring-substituted methcathinone analogs". Eur J Pharmacol 699 (1–3): 180–187. January 2013. doi:10.1016/j.ejphar.2012.11.008. PMID 23178523. 
  21. ↑ 21.0 21.1 21.2 Cozzi, Nicholas V.; Daley, Paul F.; Evans, Darin L.; Partilla, John S.; Rothman, Richard B.; Ruoho, Arnold E.; Baumann, Michael H. (2011). "Trifluoromethyl ring-substituted methcathinone analogs: activity at monoamine uptake transporters". The FASEB Journal 25 (S1). doi:10.1096/fasebj.25.1_supplement.1083.1. ISSN 0892-6638. 
  22. ↑ 22.00 22.01 22.02 22.03 22.04 22.05 22.06 22.07 22.08 22.09 22.10 22.11 22.12 22.13 "Hybrid dopamine uptake blocker-serotonin releaser ligands: a new twist on transporter-focused therapeutics". ACS Med Chem Lett 5 (6): 623–627. June 2014. doi:10.1021/ml500113s. PMID 24944732. 
  23. ↑ "Norfenfluramine to treat dravet syndrome". 9 March 2023. https://patents.google.com/patent/US20230076320A1/en. 
  24. ↑ 24.00 24.01 24.02 24.03 24.04 24.05 24.06 24.07 24.08 24.09 24.10 Shalabi, Abdelrahman R. (14 December 2017). Structure-Activity Relationship Studies of Bupropion and Related 3-Substituted Methcathinone Analogues at Monoamine Transporters. VCU Scholars Compass (Thesis). doi:10.25772/M4E1-3549. Retrieved 24 November 2024.
  25. ↑ 25.0 25.1 25.2 "Deconstructed Analogues of Bupropion Reveal Structural Requirements for Transporter Inhibition versus Substrate-Induced Neurotransmitter Release". ACS Chem Neurosci 8 (6): 1397–1403. June 2017. doi:10.1021/acschemneuro.7b00055. PMID 28220701. 
  26. ↑ "Bupropion and bupropion analogs as treatments for CNS disorders". Emerging Targets & Therapeutics in the Treatment of Psychostimulant Abuse. Adv Pharmacol. 69. Academic Press. 2014. pp. 177–216. doi:10.1016/B978-0-12-420118-7.00005-6. ISBN 978-0-12-420118-7. 
  27. ↑ "Effects of methcathinone and 3-Cl-methcathinone (PAL-434) in cocaine discrimination or self-administration in rhesus monkeys". Int J Neuropsychopharmacol 16 (9): 1985–1998. October 2013. doi:10.1017/S146114571300059X. PMID 23768644. 
  28. ↑ 28.0 28.1 28.2 Yadav, Barkha J (16 July 2019). Understanding Structure–Activity Relationship of Synthetic Cathinones (Bath Salts) Utilizing Methylphenidate. VCU Scholars Compass (Thesis). doi:10.25772/MJQW-8C64. Retrieved 24 November 2024.
  29. ↑ & Sean Dalziel"Specialized combinations for mental disorders or mental enhancement" US patent 20240335414, published 10 October 2024
  30. ↑ 30.0 30.1 30.2 30.3 30.4 "Neuropharmacology of Synthetic Cathinones". Handb Exp Pharmacol. Handbook of Experimental Pharmacology 252: 113–142. 2018. doi:10.1007/164_2018_178. ISBN 978-3-030-10560-0. PMID 30406443. 
  31. ↑ 31.0 31.1 31.2 31.3 31.4 31.5 31.6 31.7 Sakloth, Farhana (11 December 2015). Psychoactive synthetic cathinones (or 'bath salts'): Investigation of mechanisms of action. VCU Scholars Compass (Thesis). doi:10.25772/AY8R-PW77. Retrieved 24 November 2024.
  32. ↑ 32.0 32.1 32.2 32.3 32.4 32.5 "Quantitative structure-activity relationship analysis of the pharmacology of para-substituted methcathinone analogues". Br J Pharmacol 172 (10): 2433–2444. May 2015. doi:10.1111/bph.13030. PMID 25438806. 
  33. ↑ 33.0 33.1 33.2 33.3 33.4 33.5 "Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones". Neuropharmacology 245. March 2024. doi:10.1016/j.neuropharm.2023.109827. PMID 38154512. 
  34. ↑ Nicole, Lauren (2022). "In vivo Structure-Activity Relationships of Substituted Amphetamines and Substituted Cathinones". https://www.proquest.com/openview/a207e98868b4a9c5ac9296fb24abbcd8/. "FIGURE 2-6: Release: Effects of the specified test drug on monoamine release by DAT (red circles), NET (blue squares), and SERT (black traingles) in rat brain tissue. [...] EC50 values determined for the drug indicated within the panel. [...]" 
  35. ↑ "The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse". J Med Chem 60 (7): 2605–2628. April 2017. doi:10.1021/acs.jmedchem.7b00085. PMID 28244748. "Table 5. Action of MDMA, MDA, and PMMA as Releasing Agents at the Serotonin (SERT), Dopamine (DAT), and Norepinephrine (NET) Transporters18,59,60 [...] a Data, although from different publications, were obtained from the same laboratory.". 
  36. ↑ "Investigation of the Optical Isomers of Methcathinone, and Two Achiral Analogs, at Monoamine Transporters and in Intracranial Self-Stimulation Studies in Rats". ACS Chem Neurosci 11 (12): 1762–1769. June 2020. doi:10.1021/acschemneuro.9b00617. PMID 32356961. 
  37. ↑ Nguyen, Vy (2019). "Analyzing Interactions Between Methcathinone Analogs and the Human Monoamine Transporters". VCU Theses and Dissertations. doi:10.25772/T1DW-MG60. 
  38. ↑ 38.0 38.1 38.2 Davies, Rachel A (10 July 2019). Structure-Activity Relationship Studies of Synthetic Cathinones and Related Agents. VCU Scholars Compass (Thesis). doi:10.25772/TZSA-0396. Retrieved 24 November 2024.
  39. ↑ 39.0 39.1 "Uptake and release effects of diethylpropion and its metabolites with biogenic amine transporters". Bioorganic & Medicinal Chemistry 8 (12): 2689–2692. December 2000. doi:10.1016/s0968-0896(00)00210-8. PMID 11131159. 
  40. ↑ "Profiling CNS Stimulants with a High-Throughput Assay for Biogenic Amine Transporter Substrates". Problems of Drug Dependence 1999: Proceedings of the 61st Annual Scientific Meeting, The College on Problems of Drug Dependence, Inc. NIDA Res Monogr. 180. 1999. pp. 1–476 (252). https://archives.nida.nih.gov/sites/default/files/180.pdf#page=261. "Diethylpropion, which is self-administered, was a weak DA uptake inhibitor (Ki = 15 µM) and NE uptake inhibitor (Ki = 18.1 µM) and essentially inactive in the other assays." 
  41. ↑ 41.0 41.1 "The synthetic cathinones, butylone and pentylone, are stimulants that act as dopamine transporter blockers but 5-HT transporter substrates". Psychopharmacology (Berl) 236 (3): 953–962. March 2019. doi:10.1007/s00213-018-5075-5. PMID 30345459. 
  42. ↑ "Substituted methcathinones differ in transporter and receptor interactions". Biochem Pharmacol 85 (12): 1803–1815. June 2013. doi:10.1016/j.bcp.2013.04.004. PMID 23583454. 
  43. ↑ "Amphetamine, past and present--a pharmacological and clinical perspective". Journal of Psychopharmacology 27 (6): 479–496. June 2013. doi:10.1177/0269881113482532. PMID 23539642. 
  44. ↑ 44.0 44.1 44.2 44.3 44.4 "Abuse-related neurochemical and behavioral effects of cathinone and 4-methylcathinone stereoisomers in rats". Eur Neuropsychopharmacol 26 (2): 288–297. February 2016. doi:10.1016/j.euroneuro.2015.12.010. PMID 26738428. 
  45. ↑ "Monoamine transporters and psychostimulant drugs". European Journal of Pharmacology 479 (1–3): 23–40. October 2003. doi:10.1016/j.ejphar.2003.08.054. PMID 14612135. 
  46. ↑ 46.0 46.1 46.2 46.3 "Eutylone and Its Structural Isomers Interact with Monoamine Transporters and Induce Locomotor Stimulation". ACS Chem Neurosci 12 (7): 1170–1177. April 2021. doi:10.1021/acschemneuro.0c00797. PMID 33689284. 
  47. ↑ "Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine". Bioorg Med Chem 23 (17): 5574–5579. September 2015. doi:10.1016/j.bmc.2015.07.035. PMID 26233799. 
  48. ↑ 48.0 48.1 "Analytical quantification, intoxication case series, and pharmacological mechanism of action for N-ethylnorpentylone (N-ethylpentylone or ephylone)". Drug Test Anal 11 (3): 461–471. March 2019. doi:10.1002/dta.2502. PMID 30207090. 
  49. ↑ 49.0 49.1 49.2 49.3 49.4 49.5 49.6 Cite error: Invalid <ref> tag; no text was provided for refs named GlennonDukat2017
  50. ↑ 50.0 50.1 50.2 50.3 "Pharmacokinetic Profiles and Pharmacodynamic Effects for Methylone and Its Metabolites in Rats". Neuropsychopharmacology 42 (3): 649–660. February 2017. doi:10.1038/npp.2016.213. PMID 27658484. 
  51. ↑ 51.0 51.1 "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology 38 (4): 552–562. March 2013. doi:10.1038/npp.2012.204. PMID 23072836. 
  52. ↑ 52.0 52.1 "Stereochemistry of mephedrone neuropharmacology: enantiomer-specific behavioural and neurochemical effects in rats". Br J Pharmacol 172 (3): 883–894. February 2015. doi:10.1111/bph.12951. PMID 25255824. 
  53. ↑ "Synthesis, characterization and monoamine transporter activity of the new psychoactive substance mexedrone and its N-methoxy positional isomer, N-methoxymephedrone". Drug Test Anal 9 (3): 358–368. March 2017. doi:10.1002/dta.2053. PMID 27524685. 
  54. ↑ "Phase I metabolites of mephedrone display biological activity as substrates at monoamine transporters". Br J Pharmacol 173 (17): 2657–2668. September 2016. doi:10.1111/bph.13547. PMID 27391165. 
  55. ↑ Europol 2008 Annual Report on the implementation of Council Decision 2005/387/JHA
  56. ↑ Europol 2009 Annual Report on the implementation of Council Decision 2005/387/JHA
  57. ↑ Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA
  58. ↑ Europol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA
  59. ↑ Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA
  60. ↑ Europol 2013 Annual Report on the implementation of Council Decision 2005/387/JHA
  61. ↑ Europol 2014 Annual Report on the implementation of Council Decision 2005/387/JHA
  62. ↑ Europol 2015 Annual Report on the implementation of Council Decision 2005/387/JHA
  63. ↑ Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA
  64. ↑ Europol 2017 Annual Report on the implementation of Council Decision 2005/387/JHA
  65. ↑ 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 978-92-9497-558-4. https://www.emcdda.europa.eu/system/files/publications/13464/20205648_TD0320796ENN_PDF_rev.pdf. 
  66. ↑ "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. 
  67. ↑ "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. 
  68. ↑ "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. 
  69. ↑ "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. 
  70. ↑ "Analytische Daten neuer 2-aminosubstituierter Methylendioxyvalerophenonderivate.". Toxichem Krimtech 83 (1): 3–29. January 2016. 
  71. ↑ "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. 
  72. ↑ "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. 
  73. ↑ "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. 
  74. ↑ "New psychoactive versus conventional stimulants - a ten-year review of casework in Hungary". Legal Medicine 47. November 2020. doi:10.1016/j.legalmed.2020.101780. PMID 32882537. 
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  77. ↑ Advisory Council on the Misuse of Drugs (UK). Consideration of the cathinones. 31 March 2010. Retrieved 2011-07-17.
  78. ↑ "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. 
  79. ↑ "NRG-1 'legal high' drug is banned". BBC News. 2010-07-12. https://www.bbc.co.uk/news/10602398. 
  80. ↑ "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. 
  81. ↑ "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. 
  82. ↑ "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. 
  83. ↑ 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.
  84. ↑ "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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