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Substituted cathinone

From Wikipedia, the free encyclopedia

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, 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

[edit]

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

Monoamine release profiles of cathinones in rat brain synaptosomes (EC50Tooltip half-maximal effective concentration, 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][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][22]
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-tBu-MC ND IA ND 942
(E max Tooltip maximal efficacy ≈ 50%)		 ND [35]
4-TFMeO-MC ND 118 ND 7510 ND [19]
4-TFMMC (4-TFMAP) ND 190–270 900 2700–4230 SNRA [36][30][20][21][32][18]
α-Me-MC (βk-mephentermine; RAD-081) ND 12860 153 590 NDRA [37][38][39]</ref>[39]
AMAPN ND 21 ND 55 ND [19][28]
Amfepramone (diethylpropion) ND >10000 >10000 >10000 PD [40][41]
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 [39][25][24]
Butylone (βk-MBDB) ND 330 IA (RI) IA (RI) SRA/NDRI [42][43]
Cathinone (C; βk-AMPH) ND 6100–7595 23.6–25.6 34.8–83.1 NDRA [17][44][19][33]
  D-Cathinone ND >10000 72.0 183.9 NDRA [45]
  L-Cathinone ND 2366–9267 12.4–28 18–24.6 NDRA [46][25][45]
Dibutylone ND IA IA (RI) IA (RI) DRI [47]
EDMC ND 347 327 496 SNDRA [48][31]
Ephylone ND IA (RI) IA (RI) IA (RI) IA (NDRI) [49]
Ethcathinone (EC) ND 1923–2118 88.3–99.3 267.6–>1000 NRA [40][17][33][35]
Ethylone (βk-MDEA) ND 617.4 4251 1122 SNDRA [31]
Eutylone (βk-EBDB) ND 1020 IA (RI) IA (RI) SRA/NDRI [47]
HHMC ND 14100 110 90 NDRA [50]
HMMC 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 [35][52]
  R(+)-Mephedrone ND 1470 ND 31 ND [35][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 [39]
  L-Methcathinone ND 1772 13.1 14.8 NDRA [35]
Methylone (MDMC) ND 234–708 140–270 117–220 SNDRA [12][51][31][47][50]
Mexedrone (4-MMC-MeO) ND 2525 IA (RI) IA (RI) SRA/NDRI [53]
Normephedrone (4-MC) ND 210 100 220 SNDRA [54][45][35]
  R(+)-Normephedrone ND 179 89 150 SNDRA [35][45]
  S(–)-Normephedrone ND 1592 115 391 NDRA [35][45]
Pentylone ND 476–1030
(EmaxTooltip maximal efficacy ≈ 50%)		 IA (RI) IA (RI) SRA/NDRI [42][47][49]
Propylone ND 3128 IA (RI) 975.9 SDRA [31]

List of substituted cathinones

[edit]

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


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

The following table displays notable derivatives that have been reported:[55][56][57][58][59][60][61][62][63][64][65][66][67][68][69][70][71][72][73][74][75][76]

Structure Compound R1 R2 R3 R4 CAS number
Cathinone H Me H H 71031-15-7
Methcathinone H Me H Me 5650-44-2
Ethcathinone H Me H Et 51553-17-4
Propylcathinone H Me H nPr 52597-14-5
Buphedrone H Et H Me 408332-79-6
N-Ethylbuphedrone (NEB) H Et H Et 1354631-28-9
N-Methyl-N-ethylbuphedrone H Et Me Et
Pentedrone H nPr H Me 879722-57-3
N-Ethylpentedrone H nPr H Et 18268-16-1
N-Isopropylpentedrone H nPr H iPr 18268-14-9
Hexedrone H nBu H Me 2169446-41-5
N-Ethylhexedrone H nBu H Et 18410-62-3
N-Butylhexedrone H nBu H nBu 18296-66-7
N-Isobutylhexedrone (NDH) H nBu H i-Bu
Isohexedrone H iBu H Me
N-Ethylheptedrone H nPe H Et
Octedrone H hexyl H Me
Dimethylcathinone H Me Me Me 15351-09-4
Diethylpropion H Me Et Et 134-80-5
N-Methyl-N-ethylcathinone H Me Me Et 1157739-24-6
Bupropion 3-Cl Me H t-Bu 34911-55-2
Hydroxybupropion 3-Cl Me H 2-Me-3-OH-propan-2-yl 357399-43-0
Mephedrone 4-Me Me H Me 1189805-46-6
2-MMC 2-Me Me H Me 1246911-71-6
2-MEC 2-Me Me H Et 1439439-84-5
2-EMC 2-Et Me H Me
2-EEC 2-Et Me H Et 2446466-59-5
3-MMC 3-Me Me H Me 1246816-62-5
3-MEC 3-Me Me H Et 1439439-83-4
3-MPC 3-Me Me H nPr
3-EMC 3-Et Me H Me
3-EEC 3-Et Me H Et 2446466-61-9
4-EMC 4-Et Me H Me 1225622-14-9
4-EEC 4-Et Me H Et 2446466-62-0
4-MC 4-Me Me H H 31952-47-3
Benzedrone 4-Me Me H Bn 1225617-75-3
2'-MeO-Benzedrone 4-Me Me H 2-MeO-Bn
2,N-Dimethylbenzedrone 2-Me Me Me Bn
3,N-Dimethylbenzedrone 3-Me Me Me Bn
4,N-Dimethylbenzedrone 4-Me Me Me Bn
4-MEC 4-Me Me H Et 1225617-18-4
4-MPC 4-Me Me H nPr
N,N-DMMC 4-Me Me Me Me 1448845-14-4
N,N-MEMC 4-Me Me Me Et
N,N-DEMC 4-Me Me Et Et 676316-90-8
4-MEAP 4-Me Pr H Et 746540-82-9
EDMC 4-Et Me Me Me
2,3-DMMC 2,3-dimethyl Me H Me
2,3-DMEC 2,3-dimethyl Me H Et
2,4-DMMC 2,4-dimethyl Me H Me 1225623-63-1
2,4-DMEC 2,4-dimethyl Me H Et 1225913-88-1
2,5-DMMC 2,5-dimethyl Me H Me
2,5-DMEC 2,5-dimethyl Me H Et
2,6-DMMC 2,6-dimethyl Me H Me
2,6-DMEC 2,6-dimethyl Me H Et
3,4-DMMC 3,4-dimethyl Me H Me 1082110-00-6
3,4-DMEC 3,4-dimethyl Me H Et 1225811-81-3
3,5-DMEC 3,5-dimethyl Me H Et
2,4,5-TMMC 2,4,5-trimethyl Me H Me 1368603-85-3
2,4,5-TMOMC 2,4,5-trimethoxy Me H Me
3,4,5-TMOMC 3,4,5-trimethoxy Me H Me
Methedrone 4-MeO Me H Me 530-54-1
Dimethedrone 4-MeO Me Me Me 91564-39-5
Ethedrone 4-MeO Me H Et
2-MOMC 2-MeO Me H Me
3-MOMC 3-MeO Me H Me 1435933-70-2
3-FC 3-F Me H H 1082949-91-4
4-FC 4-F Me H H 80096-51-1
2-FMC 2-F Me H Me 1186137-35-8
2-FEC 2-F Me H Et
3-FMC 3-F Me H Me 1049677-77-1
3-FEC 3-F Me H Et
2-CMC 2-Cl Me H Me
2-BMC 2-Br Me H Me
2-IMC 2-I Me H Me
2-TFMAP 2-CF3 Me H Me
Clophedrone (3-CMC) 3-Cl Me H Me 1049677-59-9
3-CEC 3-Cl Me H Et 2150476-60-9
3-BMC 3-Br Me H Me 676487-42-6
3-IMC 3-I Me H Me
3-TFMAP 3-CF3 Me H Me
Flephedrone 4-F Me H Me 447-40-5
4-FEC 4-F Me H Et 1225625-74-0
Clephedrone (4-CMC) 4-Cl Me H Me 1225843-86-6
2-CEC 2-Cl Me H Et
4-CEC 4-Cl Me H Et 14919-85-8
2-CiPC 2-Cl Me H iPr
3-CiPC 3-Cl Me H iPr
4-CiPC 4-Cl Me H iPr
4-CBC 4-Cl Me H nBu 1225621-71-5
2-CDMC 2-Cl Me Me Me
3-CDMC 3-Cl Me Me Me
4-CDMC 4-Cl Me Me Me 1157667-29-2
Brephedrone 4-Br Me H Me 486459-03-4
4-BEC 4-Br Me H Et 135333-26-5
4-IMC 4-I Me H Me
4-TFMAP 4-CF3 Me H Me
4-EFMC 4-(2-fluoroethyl) Me H Me
4-MTMC 4-SCH3 Me H Me
4-MSMC 4-SO2CH3 Me H Me
4-PHMC 4-phenyl Me H Me
Mexedrone 4-Me methoxymethyl H Me
FMMC 3-F-4-Me Me H Me 1696642-00-8
MFMC 3-Me-4-F Me H Me 1368943-21-8
4-Cl-3-MMC 3-Me-4-Cl Me H Me
MMOMC 3-Me-4-MeO Me H Me
3,4-DCMC 3,4-dichloro Me H Me 802281-39-6
3,4-DCEC 3,4-dichloro Me H Et 1225618-63-2
3,5-DCMC 3,5-dichloro Me H Me
3,5-DFMC 3,5-difluoro Me H Me 1430343-55-7
2,5-DMOMC 2,5-dimethoxy Me H Me
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
βk-2C-I 2,5-dimethoxy-4-iodo H H H
βk-2C-D 2,5-dimethoxy-4-methyl H H H 1368627-25-1
βk-2C-E 2,5-dimethoxy-4-ethyl H H H 1517021-02-1
βk-2C-P 2,5-dimethoxy-4-propyl H H H
βk-2C-iP 2,5-dimethoxy-4-isopropyl H H H 1511033-62-7
βk-DOB 2,5-dimethoxy-4-bromo Me H H
βk-MDOM 2,5-dimethoxy-4-methyl Me H Me
βk-MDA 3,4-methylenedioxy Me H H 80535-73-5
N-Acetyl-βk-MDA 3,4-methylenedioxy Me H acetyl
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
N-Acetylmethylone 3,4-methylenedioxy Me acetyl Me
N-Hydroxymethylone 3,4-methylenedioxy Me hydroxy Me
Ethylone 3,4-methylenedioxy Me H Et 1112937-64-0
Diethylone 3,4-methylenedioxy Me Et Et
N-Acetylethylone 3,4-methylenedioxy Me acetyl Et
N-Isopropyl-βk-MDA 3,4-methylenedioxy Me H iPr
MDPT 3,4-methylenedioxy Me H t-Bu 186028-84-2
Benzylone (BMDP) 3,4-methylenedioxy Me H Bn 1823274-68-5
N-Cyclohexylmethylone 3,4-methylenedioxy Me H cyclohexyl
3,4-EDMC 3,4-ethylenedioxy Me H Me 30253-44-2
βk-IMP 3,4-trimethylene Me H Me 100608-69-3
βk-IBP 3,4-trimethylene Et H Et
βk-IVP 3,4-trimethylene nPr H Et
3-Fluorobuphedrone 3-F Et H Me
4-Fluorobuphedrone 4-F Et H Me 1368599-12-5
4-Bromobuphedrone 4-Br Et H Me
3-Methylbuphedrone 3-Me Et H Me 1797911-07-9
4-Me-MABP 4-Me Et H Me 1336911-98-8
4-Me-NEB 4-Me Et H Et 18268-19-4
2-F-NEB 2-F Et H Et
3F-NEB 3-F Et H Et
4-F-NEB 4-F Et H Et
4-Me-DMB 4-Me Et Me Me
3,4-DMEB 3,4-dimethyl Et H Et
4-Methoxybuphedrone 4-MeO Et H Me
Butylone 3,4-methylenedioxy Et H Me 802575-11-7
Eutylone 3,4-methylenedioxy Et H Et 802855-66-9
βk-PBDB 3,4-methylenedioxy Et H nPr
Bn-4-MeMABP 4-Me Et H Bn 1445751-39-2
BMDB 3,4-methylenedioxy Et H Bn 1445751-47-2
N-Cyclohexylbutylone 3,4-methylenedioxy Et H cyclohexyl
βk-DMBDB 3,4-methylenedioxy Et Me Me 802286-83-5
βk-MMDMA 3,4-methylenedioxy-5-MeO Me H Me 2230716-98-8
βk-MMDMA-2 2-MeO-3,4-methylenedioxy Me H Me
βk-DMMDA 2,5-diMeO-3,4-methylenedioxy Me H H
5-Methylmethylone 3,4-methylenedioxy-5-Me Me H Me 1364933-83-4
5-Methylethylone 3,4-methylenedioxy-5-Me Me H Et 1364933-82-3
2-Methylbutylone 2-Me-3,4-methylenedioxy Et H Me 1364933-86-7
5-Methylbutylone 3,4-methylenedioxy-5-Me Et H Me 1354631-29-0
Pentylone 3,4-methylenedioxy nPr H Me 698963-77-8
N-Ethylpentylone 3,4-methylenedioxy nPr H Et 727641-67-0
N-propylpentylone 3,4-methylenedioxy nPr H nPr
N-butylpentylone 3,4-methylenedioxy nPr H nBu
2,3-Dipentylone 2,3-methylenedioxy nPr Me Me
Dipentylone 3,4-methylenedioxy nPr Me Me 17763-13-2
N,N-Diethylnorpentylone 3,4-methylenedioxy nPr Et Et
Hexylone 3,4-methylenedioxy nBu H Me
Isohexylone 3,4-methylenedioxy iBu H Me 1157947-89-1
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
3,4-DMEP 3,4-dimethyl nPr H Et
2-F-Pentedrone 2-F nPr H Me
3-F-Pentedrone 3-F nPr H Me
4-F-Pentedrone 4-F nPr H Me
4-Cl-Pentedrone 4-Cl nPr H Me 2167949-43-9
4-Methylpentedrone 4-Me nPr H Me 1373918-61-6
DL-4662 3,4-dimethoxy nPr H Et 1674389-55-9
4-F-iPr-norpentedrone 4-F nPr H iPr
3-CBV 3-Cl nPr H tBu
4-methylhexedrone 4-Me nBu H Me
MEH 4-Me nBu H Et
3F-NEH 3-F nBu H Et
4-F-hexedrone 4-F nBu H Me
4-F-octedrone 4-F hexyl H Me
α-phenylmephedrone 4-Me phenyl H Me
βk-Ephenidine H phenyl H Et 22312-16-9
BMAPN β-naphthyl instead of phenyl Me H Me
βk-Methiopropamine thiophen-2-yl instead of phenyl Me H Me 24065-17-6
5-Cl-bk-MPA 5-chlorothiophen-2-yl instead of phenyl Me H Me
βk-5-MAPB benzofuran-5-yl instead of phenyl Me H Me
βk-6-MAPB benzofuran-6-yl instead of phenyl Me H Me
βk-5-IT indol-5-yl instead of phenyl Me H H 1369231-36-6
βk-5F-NM-AMT[77] 5-fluoroindol-3-yl instead of phenyl Me H Me
α-Phthalimidopropiophenone H Me phthalimido 19437-20-8
PPPO H Me piperidinyl
PPBO H Et piperidinyl 92728-82-0
FPPVO 4-F nPr piperidinyl
3,4-Pr-PipVP 3,4-trimethylene nPr piperidinyl
MDPV-azepane 3,4-methylenedioxy nPr azepane
Caccure 907 4-SCH3 α,α-di-Me morpholinyl
α-PPP H Me pyrrolidinyl 19134-50-0
α-PBP H Et pyrrolidinyl 13415-54-8
α-PVP (O-2387) H nPr pyrrolidinyl 14530-33-7
α-PHP H nBu pyrrolidinyl 13415-86-6
α-PHiP H iBu pyrrolidinyl
α-PEP (α-PHPP) H nPe pyrrolidinyl 13415-83-3
α-POP H hexyl pyrrolidinyl
α-PNP H heptyl pyrrolidinyl
DPPE (Alpha-D2PV) H phenyl pyrrolidinyl 27590-61-0
α-PcPeP H cyclopentyl pyrrolidinyl
α-PCYP H cyclohexyl pyrrolidinyl 1803168-11-7
2-MePPP 2-Me Me pyrrolidinyl 2092429-83-7
3-MePPP 3-Me Me pyrrolidinyl 1214940-01-8
4-MePPP 4-Me Me pyrrolidinyl 1313393-58-6
3-MeO-PPP 3-MeO Me pyrrolidinyl
MOPPP 4-MeO Me pyrrolidinyl 478243-09-3
3-F-PPP 3-F Me pyrrolidinyl 1214939-99-7
FPPP 4-F Me pyrrolidinyl 28117-76-2
Cl-PPP 4-Cl Me pyrrolidinyl 93307-24-5
3-Br-PPP 3-Br Me pyrrolidinyl
Br-PPP 4-Br Me pyrrolidinyl
2,3-DMPPP 2,3-dimethyl Me pyrrolidinyl
2,4-DMPPP 2,4-dimethyl Me pyrrolidinyl
3,4-DMPPP 3,4-dimethyl Me pyrrolidinyl
3-MPBP 3-Me Et pyrrolidinyl 1373918-60-5
3-F-PBP 3-F Et pyrrolidinyl 1373918-59-2
MPBP 4-Me Et pyrrolidinyl 732180-91-5
FPBP 4-F Et pyrrolidinyl 1373918-67-2
EPBP 4-Et Et pyrrolidinyl
MOPBP 4-MeO Et pyrrolidinyl
MMOPBP 3-Me-4-MeO Et pyrrolidinyl
O-2384 3,4-dichloro Et pyrrolidinyl 850352-65-7
2-Me-PVP 2-Me nPr pyrrolidinyl 850352-54-4
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
3F-PVP 3-F nPr pyrrolidinyl 2725852-55-9
FPVP 4-F nPr pyrrolidinyl 850352-31-7
2-Cl-PVP 2-Cl nPr pyrrolidinyl
3-Cl-PVP 3-Cl nPr pyrrolidinyl
4-Cl-PVP 4-Cl nPr pyrrolidinyl 5537-17-7
3-Br-PVP 3-Br nPr pyrrolidinyl
4-Br-PVP 4-Br nPr pyrrolidinyl
MOPVP 4-MeO nPr pyrrolidinyl 5537-19-9
DMOPVP 3,4-dimethoxy nPr pyrrolidinyl 850442-84-1
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
DMOPHP 3,4-dimethoxy nBu pyrrolidinyl
MFPHP 3-Me-4-F nBu pyrrolidinyl
3F-PiHP 3-F iBu pyrrolidinyl
4F-PiHP 4-F iBu pyrrolidinyl
O-2394 4-Me iBu pyrrolidinyl 850352-51-1
MPEP 4-Me pentyl pyrrolidinyl
4F-PV8 4-F pentyl pyrrolidinyl
4-MeO-PV8 4-MeO pentyl pyrrolidinyl
MFPEP 3-Me-4-F pentyl pyrrolidinyl
MCPEP 3-Me-4-Cl pentyl pyrrolidinyl
4F-PV9 4-F hexyl pyrrolidinyl
4-MeO-PV9 4-MeO hexyl pyrrolidinyl
α-Phenylpyrovalerone 4-Me phenyl pyrrolidinyl
MDPPP 3,4-methylenedioxy Me pyrrolidinyl 783241-66-7
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
2,3-MDPV 2,3-methylenedioxy nPr pyrrolidinyl
5-Me-MDPV 3,4-methylenedioxy-5-Me nPr pyrrolidinyl
6-Me-MDPV 2-Me-4,5-methylenedioxy nPr pyrrolidinyl
6-MeO-MDPV 2-MeO-4,5-methylenedioxy nPr pyrrolidinyl
Br-MeO-MDPV 2,3-methylenedioxy-4-MeO-5-Br nPr pyrrolidinyl
MDPiVP 3,4-methylenedioxy iPr pyrrolidinyl
MDPHP 3,4-methylenedioxy nBu pyrrolidinyl 776994-64-0
MDPHiP 3,4-methylenedioxy iBu pyrrolidinyl
MDPEP (MD-PV8) 3,4-methylenedioxy pentyl pyrrolidinyl 24646-39-7
MDPOP (MD-PV9) 3,4-methylenedioxy hexyl pyrrolidinyl 24646-40-0
3,4-EtPV 3,4-dimethylene nPr pyrrolidinyl
5-PPDi 3,4-trimethylene Et pyrrolidinyl
Indanyl-α-PVP 3,4-trimethylene nPr pyrrolidinyl 2748590-83-0
5-BPDi 3,4-trimethylene nBu pyrrolidinyl
IPPV 3,4-trimethylene phenyl pyrrolidinyl
TH-PBP 3,4-tetramethylene Et pyrrolidinyl
TH-PVP 3,4-tetramethylene nPr pyrrolidinyl 2304915-07-7
TH-PHP 3,4-tetramethylene nBu pyrrolidinyl
5-DBFPV 2,3-dihydrobenzofuran-5-yl instead of Ph nPr pyrrolidinyl 1620807-94-4
3-BF-PVP benzofuran-3-yl instead of Ph nPr pyrrolidinyl
Naphyrone (O-2482) β-naphthyl instead of phenyl nPr pyrrolidinyl 850352-53-3
α-Naphyrone α-naphthyl instead of phenyl nPr pyrrolidinyl
α-PPT thiophen-2-yl instead of phenyl Me pyrrolidinyl
α-PBT thiophen-2-yl instead of phenyl Et pyrrolidinyl
α-PVT thiophen-2-yl instead of phenyl nPr pyrrolidinyl 1400742-66-6

Legality

[edit]

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.[78]

"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.[79] 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,[80][81] along with a further broad based structure ban even more expansive than the last.[82][83]

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

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

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

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

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

by inclusion of the 2-amino nitrogen atom in a cyclic structure".

— Home Office, 13 July 2010.
General chemical structure of substituted naphyrones, with R1-R3 defined in text

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

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

More new derivatives have however continued to appear, with the UK reporting more novel cathinone derivatives detected in 2010 than any other country in Europe, with most of them first identified after the generic ban had gone into effect and thus already being illegal despite never having been previously reported.[84]

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.[85]

See also

[edit]

References

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