Substituted cathinone explained

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. 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.

Name SerotoninNorepinephrineDopamineTypeReferences
2837 156 650 NDRA
2815 93 179 NDRA
>10000
48.7 NDRA - 7220 339 920 NDRA - 347–490 53 81–97.9 SNDRA - >10000
>10000 - 2-TFMMC (2-TFMAP) 8400–>10000 2200
8000–>10000 SNDRA [17] - PAL-586 621 [18] [19] - 136–137 25 21–28.0 SNDRA - 567 105 64 SNDRA - 3-CCPC (RTI-6037-39) PAL-433 1328 [20] - (–)-3-CCPC PAL-1122 562 - (+)-3-CCPC PAL-1123 733 - PAL-361 - PAL-820 181 - 3-CMC (clophedrone) PAL-434 211–410 19–54.4 26–46.8 SNDRA [21] - PAL-363 - 1460
64.8 NDRA - PAL-588 1067 - PAL-591 1014 - 306–683 111
109–129 SNDRA [22] [23] - 268–292 27 28–70.6 SNDRA - 188
729 SNDRA - 3-TFMMC (3-TFMAP) 297–380 2700
610–1290 SNDRA - PAL-787 356 - 4-BMC (brephedrone) 42.5–60.2 100 59.4 SNDRA [24] - 128.4 85.1 221.8 SNDRA [25] [26] - PAL-743 1632 - 152.6 5194.0 353.6 SDRA - 4-CMC (clephedrone) 71.1–144 44–90.9 42.2–74.7 SNDRA - 4-FMC (flephedrone) 1290–1450 62 83.4–119 NDRA [27] - PAL-744 667 - 4-MeO-MC (methedrone) 120–195 111 506–881 SNDRA - 942
(≈ 50%) 		[28] - 118 7510 - 4-TFMMC (4-TFMAP) 190–270 900 2700–4230 SNRA [29] [30] [31] - α-Me-MC (βk-mephentermine; RAD-081) 12860 153 590 NDRA [32] [33] - 21 55 [34] - Amfepramone (diethylpropion) >10000 >10000 >10000 [35] [36] - 27 34 - Buphedrone (βk-MEPEA) PAL-429 411 - Bupropion (amfebutamone) NDRI [37] [38] - Butylone (βk-MBDB) 330 SRA/NDRI [39] [40] - Cathinone (C; βk-AMPH) 6100–7595 23.6–25.6 34.8–83.1 NDRA [41] [42] - -Cathinone >10000 72.0 183.9 NDRA [43] - -Cathinone 2366–9267 12.4–28 18–24.6 NDRA [44] - DRI - 347 327 496 SNDRA [45] - (NDRI) [46] - Ethcathinone (EC) 1923–2118 88.3–99.3 267.6–>1000 NRA - Ethylone (βk-MDEA) 617.4 4251 1122 SNDRA - Eutylone (βk-EBDB) 1020 SRA/NDRI [47] - 14100 110 90 NDRA - 7210 6340 5840 SNDRA - 966 394 370 SNDRA - Mephedrone (4-MMC) 118.3–122 58–62.7 49.1–51 SNDRA [48] - S(–)-Mephedrone 61 74 [49] - R(+)-Mephedrone 1470 31 - Methcathinone (MC) 2592–5853 22–26.1 12.5–49.9 NDRA [50] [51] - -Methcathinone NRA - -Methcathinone 1772 13.1 14.8 NDRA - Methylone (MDMC) 234–708 140–270 117–220 SNDRA [52] - Mexedrone (4-MMC-MeO) 2525 SRA/NDRI [53] - Normephedrone (4-MC) 210 100 220 SNDRA [54] - R(+)-Normephedrone 179 89 150 SNDRA - S(–)-Normephedrone 1592 115 391 NDRA - 476–1030
(≈ 50%) 		SRA/NDRI - 3128 975.9 SDRA

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

StructureCompoundR1R2R3R4CAS #
H H 71031-15-7
H Me H Me 5650-44-2
H Me H 51553-17-4
H Me H 52597-14-5
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
H nPr H Me 879722-57-3
H nPr H Et 18268-16-1
N-Isopropylpentedrone H nPr H iPr 18268-14-9
H nBu H Me 2169446-41-5
H nBu H Et 18410-62-3
N-Butylhexedrone H nBu H nBu 18296-66-7
N-Isobutylhexedrone (NDH) H nBu H
Isohexedrone H iBu H Me
H nPe H Et
Octedrone H H Me
H Me Me Me 15351-09-4
H Me Et Et 134-80-5
N-Methyl-N-ethylcathinone H Me Me Et 1157739-24-6
3-Cl Me H 34911-55-2
3-Cl Me H 2-Me-3-OH-propan-2-yl 357399-43-0
4-Me Me H Me 1189805-46-6
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-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-Et Me H Me 1225622-14-9
4-EEC 4-Et Me H Et 2446466-62-0
4-Me Me H H 31952-47-3
4-Me Me H 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-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-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-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
Me H Me 530-54-1
Dimethedrone 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-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
Me H Me 447-40-5
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
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
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
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-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
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
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
3,4-methylenedioxy Me H Me 186028-79-5
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
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
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 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
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
3,4-methylenedioxy Et H Me 802575-11-7
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
3,4-methylenedioxy Et Me Me 802286-83-5
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
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
3,4-methylenedioxy nPr H Me 698963-77-8
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
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
3,4-methylenedioxy iBu H Me 1157947-89-1
Isoheptylone 3,4-methylenedioxy iPe H Me
3,4-methylenedioxy nBu H Et 27912-41-0
3,4-methylenedioxy nPe H Et
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-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
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
H phenyl H Et 22312-16-9
β-naphthyl instead of phenyl Me H Me
thiophen-2-yl instead of phenyl Me H Me 24065-17-6
5-chlorothiophen-2-yl instead of phenyl Me H Me
benzofuran-5-yl instead of phenyl Me H Me
benzofuran-6-yl instead of phenyl Me H Me
βk-5-IT indol-5-yl instead of phenyl Me H H 1369231-36-6
H Me phthalimido 19437-20-8
PPPO H Me piperidinyl
PPBO H Et piperidinyl 92728-82-0
FPPVO 4-F nPr piperidinyl
3,4-trimethylene nPr piperidinyl
MDPV-azepane 3,4-methylenedioxy nPr
Caccure 907 4-SCH3 α,α-di-Me morpholinyl
H Me pyrrolidinyl 19134-50-0
H Et pyrrolidinyl 13415-54-8
α-PVP (O-2387) H nPr pyrrolidinyl 14530-33-7
H pyrrolidinyl 13415-86-6
H iBu pyrrolidinyl
α-PEP (α-PHPP) H pyrrolidinyl 13415-83-3
α-POP H pyrrolidinyl
α-PNP H pyrrolidinyl
DPPE (Alpha-D2PV) H phenyl pyrrolidinyl 27590-61-0
α-PcPeP H pyrrolidinyl
H pyrrolidinyl 1803168-11-7
2-MePPP 2-Me Me pyrrolidinyl 2092429-83-7
3-MePPP 3-Me Me pyrrolidinyl 1214940-01-8
4-Me Me pyrrolidinyl 1313393-58-6
3-MeO-PPP 3-MeO Me pyrrolidinyl
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
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 nPr pyrrolidinyl 850352-54-4
3-Me nPr pyrrolidinyl 13415-85-5
Pyrovalerone (O-2371) 4-Me nPr pyrrolidinyl 3563-49-3
4-Et nPr pyrrolidinyl
3-F nPr pyrrolidinyl 2725852-55-9
4-F nPr pyrrolidinyl 850352-31-7
2-Cl-PVP 2-Cl nPr pyrrolidinyl
3-Cl-PVP 3-Cl nPr pyrrolidinyl
4-Cl nPr pyrrolidinyl 5537-17-7
3-Br-PVP 3-Br nPr pyrrolidinyl
4-Br-PVP 4-Br nPr pyrrolidinyl
4-MeO nPr pyrrolidinyl 5537-19-9
3,4-dimethoxy nPr pyrrolidinyl 850442-84-1
DMPVP 3,4-dimethyl nPr pyrrolidinyl
3,4-dichloro nPr pyrrolidinyl 850352-61-3
3-methyl-4-fluoro nPr pyrrolidinyl
4-Me nBu pyrrolidinyl 34138-58-4
3-F nBu pyrrolidinyl
4-F nBu pyrrolidinyl 2230706-09-7
4-Cl nBu pyrrolidinyl 2748592-29-0
DMOPHP 3,4-dimethoxy nBu pyrrolidinyl
MFPHP 3-Me-4-F nBu pyrrolidinyl
3-F iBu pyrrolidinyl
4F-PiHP 4-F iBu pyrrolidinyl
O-2494 4-Me pyrrolidinyl 850352-51-1
MPEP 4-Me 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
4-F pyrrolidinyl
4-MeO-PV9 4-MeO hexyl pyrrolidinyl
α-Phenylpyrovalerone 4-Me pyrrolidinyl
3,4-methylenedioxy Me pyrrolidinyl 783241-66-7
MDMPP 3,4-methylenedioxy α,α-di-Me pyrrolidinyl
3,4-methylenedioxy Et pyrrolidinyl 784985-33-7
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
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
3,4-trimethylene nBu pyrrolidinyl
3,4-trimethylene phenyl pyrrolidinyl
TH-PBP 3,4-tetramethylene Et pyrrolidinyl
3,4-tetramethylene nPr pyrrolidinyl 2304915-07-7
TH-PHP 3,4-tetramethylene nBu pyrrolidinyl
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
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]

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]

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.[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

External links

Notes and References

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  2. Paillet-Loilier M, Cesbron A, Le Boisselier R, Bourgine J, Debruyne D . Emerging drugs of abuse: current perspectives on substituted cathinones . Substance Abuse and Rehabilitation . 5 . 37–52 . 2014 . 24966713 . 4043811 . 10.2147/SAR.S37257 . free .
  3. Simmons SJ, Leyrer-Jackson JM, Oliver CF, Hicks C, Muschamp JW, Rawls SM, Olive MF . DARK Classics in Chemical Neuroscience: Cathinone-Derived Psychostimulants . ACS Chemical Neuroscience . 9 . 10 . 2379–2394 . October 2018 . 29714473 . 6197900 . 10.1021/acschemneuro.8b00147 .
  4. Beck O, Bäckberg M, Signell P, Helander A . Intoxications in the STRIDA project involving a panorama of psychostimulant pyrovalerone derivatives, MDPV copycats . Clinical Toxicology . 56 . 4 . 256–263 . April 2018 . 28895757 . 10.1080/15563650.2017.1370097 . 3401681 . free .
  5. Majchrzak M, Celiński R, Kuś P, Kowalska T, Sajewicz M . The newest cathinone derivatives as designer drugs: an analytical and toxicological review . Forensic Toxicology . 36 . 1 . 33–50 . 2018 . 29367861 . 5754390 . 10.1007/s11419-017-0385-6 .
  6. Colzato LS, Ruiz MJ, van den Wildenberg WP, Hommel B . Khat use is associated with impaired working memory and cognitive flexibility . PLOS ONE. 6 . 6 . e20602 . 2011 . 21698275 . 3115937 . 10.1371/journal.pone.0020602 . free . 2011PLoSO...620602C .
  7. Rothman RB, Baumann MH . Monoamine transporters and psychostimulant drugs . Eur. J. Pharmacol. . 479 . 1–3 . 23–40 . 2003 . 14612135 . 10.1016/j.ejphar.2003.08.054.
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  13. Kuropka P, Zawadzki M, Szpot P . A narrative review of the neuropharmacology of synthetic cathinones-Popular alternatives to classical drugs of abuse . Hum Psychopharmacol . 38 . 3 . e2866 . May 2023 . 36866677 . 10.1002/hup.2866 . 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)..
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