Substituted cathinone

Substituted cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions.[1][2][3][4][5] Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug.[6]

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

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:[7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28]

Structure Compound R1 R2 R3 R4 CAS number
CathinoneHMeHH71031-15-7
MethcathinoneHMeHMe5650-44-2
EthcathinoneHMeHEt51553-17-4
PropylcathinoneHMeHnPr52597-14-5
BuphedroneHEtHMe408332-79-6
N-Ethylbuphedrone (NEB)HEtHEt1354631-28-9
N-Methyl-N-ethylbuphedroneHEtMeEt
PentedroneHnPrHMe879722-57-3
N-EthylpentedroneHnPrHEt18268-16-1
N-IsopropylpentedroneHnPrHiPr18268-14-9
HexedroneHnBuHMe2169446-41-5
N-EthylhexedroneHnBuHEt18410-62-3
N-ButylhexedroneHnBuHnBu18296-66-7
N-Isobutylhexedrone (NDH)HnBuHi-Bu
IsohexedroneHiBuHMe
N-EthylheptedroneHnPeHEt
OctedroneHhexylHMe
DimethylcathinoneHMeMeMe15351-09-4
DiethylpropionHMeEtEt134-80-5
N-Methyl-N-ethylcathinoneHMeMeEt1157739-24-6
Bupropion (3-CBP)3-ClMeHt-Bu34911-55-2
Hydroxybupropion3-ClMeH2-Me-3-OH-propan-2-yl357399-43-0
Mephedrone4-MeMeHMe1189805-46-6
2-MMC2-MeMeHMe1246911-71-6
2-MEC2-MeMeHEt1439439-84-5
2-EMC2-EtMeHMe
2-EEC2-EtMeHEt2446466-59-5
3-MMC3-MeMeHMe1246816-62-5
3-MEC3-MeMeHEt1439439-83-4
3-EMC3-EtMeHMe
3-EEC3-EtMeHEt2446466-61-9
4-EMC4-EtMeHMe1225622-14-9
4-EEC4-EtMeHEt2446466-62-0
4-MC4-MeMeHH31952-47-3
Benzedrone4-MeMeHBn1225617-75-3
2'-MeO-Benzedrone4-MeMeH2-MeO-Bn
2,N-Dimethylbenzedrone2-MeMeMeBn
3,N-Dimethylbenzedrone3-MeMeMeBn
4,N-Dimethylbenzedrone4-MeMeMeBn
4-MEC4-MeMeHEt1225617-18-4
4-MPC4-MeMeHnPr
N,N-DMMC4-MeMeMeMe1448845-14-4
N,N-MEMC4-MeMeMeEt
N,N-DEMC4-MeMeEtEt676316-90-8
4-MEAP4-MePrHEt746540-82-9
EDMC4-EtMeMeMe
2,3-DMMC2,3-dimethylMeHMe
2,3-DMEC2,3-dimethylMeHEt
2,4-DMMC2,4-dimethylMeHMe1225623-63-1
2,4-DMEC2,4-dimethylMeHEt1225913-88-1
2,5-DMMC2,5-dimethylMeHMe
2,5-DMEC2,5-dimethylMeHEt
2,6-DMMC2,6-dimethylMeHMe
2,6-DMEC2,6-dimethylMeHEt
3,4-DMMC3,4-dimethylMeHMe1082110-00-6
3,4-DMEC3,4-dimethylMeHEt1225811-81-3
3,5-DMEC3,5-dimethylMeHEt
2,4,5-TMMC2,4,5-trimethylMeHMe1368603-85-3
2,4,5-TMOMC2,4,5-trimethoxyMeHMe
3,4,5-TMOMC3,4,5-trimethoxyMeHMe
Methedrone4-MeOMeHMe530-54-1
Dimethedrone4-MeOMeMeMe91564-39-5
Ethedrone4-MeOMeHEt
2-MOMC2-MeOMeHMe
3-MOMC3-MeOMeHMe1435933-70-2
3-FC3-FMeHH1082949-91-4
4-FC4-FMeHH80096-51-1
2-FMC2-FMeHMe1186137-35-8
2-FEC2-FMeHEt
3-FMC3-FMeHMe1049677-77-1
3-FEC3-FMeHEt
2-CMC2-ClMeHMe
2-BMC2-BrMeHMe
2-IMC2-IMeHMe
2-TFMAP2-CF3MeHMe
Clophedrone3-ClMeHMe1049677-59-9
3-CEC3-ClMeHEt2150476-60-9
3-BMC3-BrMeHMe676487-42-6
3-IMC3-IMeHMe
3-TFMAP3-CF3MeHMe
Flephedrone4-FMeHMe447-40-5
4-FEC4-FMeHEt1225625-74-0
Clephedrone4-ClMeHMe1225843-86-6
2-CEC2-ClMeHEt
4-CEC4-ClMeHEt14919-85-8
2-CiPC2-ClMeHiPr
3-CiPC3-ClMeHiPr
4-CiPC4-ClMeHiPr
4-CBC4-ClMeHnBu1225621-71-5
2-CDMC2-ClMeMeMe
3-CDMC3-ClMeMeMe
4-CDMC4-ClMeMeMe1157667-29-2
Brephedrone4-BrMeHMe486459-03-4
4-BEC4-BrMeHEt135333-26-5
4-IMC4-IMeHMe
4-TFMAP4-CF3MeHMe
4-EFMC4-(2-fluoroethyl)MeHMe
4-MTMC4-SCH3MeHMe
4-MSMC4-SO2CH3MeHMe
4-PHMC4-phenylMeHMe
Mexedrone4-MemethoxymethylHMe
FMMC3-F-4-MeMeHMe1696642-00-8
MFMC3-Me-4-FMeHMe1368943-21-8
MMOMC3-Me-4-MeOMeHMe
3,4-DCMC3,4-dichloroMeHMe802281-39-6
3,4-DCEC3,4-dichloroMeHEt1225618-63-2
3,5-DCMC3,5-dichloroMeHMe
3,5-DFMC3,5-difluoroMeHMe1430343-55-7
2,5-DMOMC2,5-dimethoxyMeHMe
βk-2C-C2,5-dimethoxy-4-chloroHHH1538191-15-9
βk-2C-B2,5-dimethoxy-4-bromoHHH807631-09-0
βk-2C-I2,5-dimethoxy-4-iodoHHH
βk-2C-D2,5-dimethoxy-4-methylHHH1368627-25-1
βk-2C-E2,5-dimethoxy-4-ethylHHH1517021-02-1
βk-2C-P2,5-dimethoxy-4-propylHHH
βk-2C-iP2,5-dimethoxy-4-isopropylHHH1511033-62-7
βk-DOB2,5-dimethoxy-4-bromoMeHH
βk-MDOM2,5-dimethoxy-4-methylMeHMe
βk-MDA3,4-methylenedioxyMeHH80535-73-5
N-Acetyl-βk-MDA3,4-methylenedioxyMeHacetyl
2,3-MDMC2,3-methylenedioxyMeHMe1427205-87-5
Methylone3,4-methylenedioxyMeHMe186028-79-5
Dimethylone3,4-methylenedioxyMeMeMe109367-07-9
N-Acetylmethylone3,4-methylenedioxyMeacetylMe
N-Hydroxymethylone3,4-methylenedioxyMehydroxyMe
Ethylone3,4-methylenedioxyMeHEt1112937-64-0
Diethylone3,4-methylenedioxyMeEtEt
N-Acetylethylone3,4-methylenedioxyMeacetylEt
N-Isopropyl-βk-MDA3,4-methylenedioxyMeHiPr
MDPT3,4-methylenedioxyMeHt-Bu186028-84-2
Benzylone (BMDP)3,4-methylenedioxyMeHBn1823274-68-5
3,4-EDMC3,4-ethylenedioxyMeHMe30253-44-2
βk-IMP3,4-trimethyleneMeHMe100608-69-3
βk-IBP3,4-trimethyleneEtHEt
βk-IVP3,4-trimethylenenPrHEt
3-Fluorobuphedrone3-FEtHMe
4-Fluorobuphedrone4-FEtHMe1368599-12-5
4-Bromobuphedrone4-BrEtHMe
3-Methylbuphedrone3-MeEtHMe1797911-07-9
4-Me-MABP4-MeEtHMe1336911-98-8
4-Me-NEB4-MeEtHEt18268-19-4
2-F-NEB2-FEtHEt
3-F-NEB3-FEtHEt
4-F-NEB4-FEtHEt
4-Me-DMB4-MeEtMeMe
3,4-DMEB3,4-dimethylEtHEt
4-Methoxybuphedrone4-MeOEtHMe
Butylone3,4-methylenedioxyEtHMe802575-11-7
Eutylone3,4-methylenedioxyEtHEt802855-66-9
βk-PBDB3,4-methylenedioxyEtHnPr
Bn-4-MeMABP4-MeEtHBn1445751-39-2
BMDB3,4-methylenedioxyEtHBn1445751-47-2
βk-DMBDB3,4-methylenedioxyEtMeMe802286-83-5
βk-MMDMA3,4-methylenedioxy-5-MeOMeHMe2230716-98-8
βk-MMDMA-22-MeO-3,4-methylenedioxyMeHMe
βk-DMMDA2,5-diMeO-3,4-methylenedioxyMeHH
5-Methylmethylone3,4-methylenedioxy-5-MeMeHMe1364933-83-4
5-Methylethylone3,4-methylenedioxy-5-MeMeHEt1364933-82-3
2-Methylbutylone2-Me-3,4-methylenedioxyEtHMe1364933-86-7
5-Methylbutylone3,4-methylenedioxy-5-MeEtHMe1354631-29-0
Pentylone3,4-methylenedioxynPrHMe698963-77-8
N-Ethylpentylone3,4-methylenedioxynPrHEt727641-67-0
N-propylpentylone3,4-methylenedioxynPrHnPr
N-butylpentylone3,4-methylenedioxynPrHnBu
2,3-Dipentylone2,3-methylenedioxynPrMeMe
Dipentylone3,4-methylenedioxynPrMeMe17763-13-2
N,N-Diethylnorpentylone3,4-methylenedioxynPrEtEt
Hexylone3,4-methylenedioxynBuHMe
Isohexylone3,4-methylenedioxyiBuHMe
N-Ethylhexylone3,4-methylenedioxynBuHEt27912-41-0
N-Ethylheptylone3,4-methylenedioxynPeHEt
4-MEAP4-MenPrHEt746540-82-9
3,4-DMEP3,4-dimethylnPrHEt
2-F-Pentedrone2-FnPrHMe
3-F-Pentedrone3-FnPrHMe
4-F-Pentedrone4-FnPrHMe
4-Cl-Pentedrone4-ClnPrHMe2167949-43-9
4-Methylpentedrone4-MenPrHMe1373918-61-6
DL-46623,4-dimethoxynPrHEt1674389-55-9
4-F-iPr-norpentedrone4-FnPrHiPr
3-CBV3-ClnPrHtBu
4-methylhexedrone4-MenBuHMe
MEH4-MenBuHEt
3F-NEH3-FnBuHEt
4-F-hexedrone4-FnBuHMe
4-F-octedrone4-FhexylHMe
α-phenylmephedrone4-MephenylHMe
βk-EphenidineHphenylHEt22312-16-9
BMAPNβ-naphthyl instead of phenylMeHMe
βk-Methiopropaminethiophen-2-yl instead of phenylMeHMe24065-17-6
5-Cl-bk-MPA5-chlorothiophen-2-yl instead of phenylMeHMe
βk-5-MAPBbenzofuran-5-yl instead of phenylMeHMe
βk-6-MAPBbenzofuran-6-yl instead of phenylMeHMe
βk-5-ITindol-5-yl instead of phenylMeHH1369231-36-6
α-PhthalimidopropiophenoneHMephthalimido19437-20-8
PPPOHMepiperidinyl
PPBOHEtpiperidinyl92728-82-0
FPPVO4-FnPrpiperidinyl
MDPV-azepane3,4-methylenedioxynPrazepane
Caccure 9074-SCH3α,α-di-Memorpholinyl
α-PPPHMepyrrolidinyl19134-50-0
α-PBPHEtpyrrolidinyl13415-54-8
α-PVP (O-2387)HnPrpyrrolidinyl14530-33-7
α-PHPHnBupyrrolidinyl13415-86-6
α-PHiPHiBupyrrolidinyl
α-PEP (α-PHPP)HnPepyrrolidinyl13415-83-3
α-POPHhexylpyrrolidinyl
α-PNPHheptylpyrrolidinyl
DPPE (A-D2PV)Hphenylpyrrolidinyl27590-61-0
α-PcPePHcyclopentylpyrrolidinyl
α-PCYPHcyclohexylpyrrolidinyl1803168-11-7
2-MePPP2-MeMepyrrolidinyl2092429-83-7
3-MePPP3-MeMepyrrolidinyl1214940-01-8
4-MePPP4-MeMepyrrolidinyl1313393-58-6
3-MeO-PPP3-MeOMepyrrolidinyl
MOPPP4-MeOMepyrrolidinyl478243-09-3
3-F-PPP3-FMepyrrolidinyl1214939-99-7
FPPP4-FMepyrrolidinyl28117-76-2
Cl-PPP4-ClMepyrrolidinyl93307-24-5
Br-PPP4-BrMepyrrolidinyl
2,3-DMPPP2,3-dimethylMepyrrolidinyl
2,4-DMPPP2,4-dimethylMepyrrolidinyl
3,4-DMPPP3,4-dimethylMepyrrolidinyl
3-MPBP3-MeEtpyrrolidinyl1373918-60-5
3-F-PBP3-FEtpyrrolidinyl1373918-59-2
MPBP4-MeEtpyrrolidinyl732180-91-5
FPBP4-FEtpyrrolidinyl1373918-67-2
EPBP4-EtEtpyrrolidinyl
MOPBP4-MeOEtpyrrolidinyl
MMOPBP3-Me-4-MeOEtpyrrolidinyl
O-23843,4-dichloroEtpyrrolidinyl850352-65-7
2-Me-PVP2-MenPrpyrrolidinyl
Pyrovalerone (O-2371)4-MenPrpyrrolidinyl3563-49-3
4-Et-PVP4-EtnPrpyrrolidinyl
3F-PVP3-FnPrpyrrolidinyl
FPVP4-FnPrpyrrolidinyl850352-31-7
2-Cl-PVP2-ClnPrpyrrolidinyl
3-Cl-PVP3-ClnPrpyrrolidinyl
4-Cl-PVP4-ClnPrpyrrolidinyl5537-17-7
4-Br-PVP4-BrnPrpyrrolidinyl
MOPVP4-MeOnPrpyrrolidinyl5537-19-9
DMOPVP3,4-dimethoxynPrpyrrolidinyl850442-84-1
DMPVP3,4-dimethylnPrpyrrolidinyl
O-23903,4-dichloronPrpyrrolidinyl850352-61-3
MFPVP3-methyl-4-fluoronPrpyrrolidinyl
MPHP4-MenBupyrrolidinyl34138-58-4
3F-PHP3-FnBupyrrolidinyl
FPHP4-FnBupyrrolidinyl2230706-09-7
4-Cl-PHP4-ClnBupyrrolidinyl
DMOPHP3,4-dimethoxynBupyrrolidinyl
3F-PiHP3-FiBupyrrolidinyl
4F-PiHP4-FiBupyrrolidinyl
O-23944-MeiBupyrrolidinyl850352-51-1
MPEP4-Mepentylpyrrolidinyl
4F-PV84-Fpentylpyrrolidinyl
4-MeO-PV84-MeOpentylpyrrolidinyl
4F-PV94-Fhexylpyrrolidinyl
4-MeO-PV94-MeOhexylpyrrolidinyl
α-Phenylpyrovalerone4-Mephenylpyrrolidinyl
MDPPP3,4-methylenedioxyMepyrrolidinyl783241-66-7
MDMPP3,4-methylenedioxyα,α-di-Mepyrrolidinyl
MDPBP3,4-methylenedioxyEtpyrrolidinyl784985-33-7
MDPV3,4-methylenedioxynPrpyrrolidinyl687603-66-3
2,3-MDPV2,3-methylenedioxynPrpyrrolidinyl
5-Me-MDPV3,4-methylenedioxy-5-MenPrpyrrolidinyl
6-Me-MDPV2-Me-4,5-methylenedioxynPrpyrrolidinyl
6-MeO-MDPV2-MeO-4,5-methylenedioxynPrpyrrolidinyl
Br-MeO-MDPV2,3-methylenedioxy-4-MeO-5-BrnPrpyrrolidinyl
MDPiVP3,4-methylenedioxyiPrpyrrolidinyl
MDPHP3,4-methylenedioxynBupyrrolidinyl776994-64-0
MDPHiP3,4-methylenedioxyiBupyrrolidinyl
MDPEP (MD-PV8)3,4-methylenedioxypentylpyrrolidinyl24646-39-7
MDPOP (MD-PV9)3,4-methylenedioxyhexylpyrrolidinyl24646-40-0
5-PPDI3,4-trimethyleneEtpyrrolidinyl
5-BPDI3,4-trimethylenenPrpyrrolidinyl
5-HPDI3,4-trimethylenenBupyrrolidinyl
IPPV3,4-trimethylenephenylpyrrolidinyl
TH-PBP3,4-tetramethyleneEtpyrrolidinyl
TH-PVP3,4-tetramethylenenPrpyrrolidinyl2304915-07-7
TH-PHP3,4-tetramethylenenBupyrrolidinyl
5-DBFPV2,3-dihydrobenzofuran-5-yl instead of PhnPrpyrrolidinyl1620807-94-4
3-BF-PVPbenzofuran-3-yl instead of PhnPrpyrrolidinyl
Naphyrone (O-2482)β-naphthyl instead of phenylnPrpyrrolidinyl850352-53-3
α-Naphyroneα-naphthyl instead of phenylnPrpyrrolidinyl
α-PPTthiophen-2-yl instead of phenylMepyrrolidinyl
α-PBTthiophen-2-yl instead of phenylEtpyrrolidinyl
α-PVTthiophen-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.[29]

"Any compound (not being bupropion or a substance for the time being specified in paragraph 2.2) structurally derived from 2-amino-1-phenyl-1-propanone by modification in any of the following ways, that is to say,

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

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

(iii) by substitution at the nitrogen atom with alkyl or dialkyl groups, or by inclusion of the nitrogen atom in a cyclic structure."

— ACMD, 2 April 2010

This text was added as an amendment to the Misuse of Drugs Act 1971, to come into force on 16 April 2010.[30] Note that four of the above compounds (cathinone, methcathinone, diethylpropion and pyrovalerone) were already illegal in the UK at the time the ACMD report was issued. Two compounds were specifically excluded from the ban, these being bupropion because of its common use in medicine and relative lack of abuse potential, and naphyrone because its structure falls outside the generic definition and not enough evidence was yet available to justify a ban.

Naphyrone analogues were subsequently banned in July 2010 following a further review by the ACMD,[31][32] along with a further broad based structure ban even more expansive than the last.[33][34]

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

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

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

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

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

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

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

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.[35]

In the United States, substituted cathinones are the psychoactive ingredients in "bath salts" which as of July 2011 were banned by at least 28 states, but not by the federal government.[36]

See also

References
  1. Meltzer PC, Butler D, Deschamps JR, Madras BK (February 2006). "1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors". Journal of Medicinal Chemistry. 49 (4): 1420–32. doi:10.1021/jm050797a. PMC 2602954. PMID 16480278.
  2. Paillet-Loilier M, Cesbron A, Le Boisselier R, Bourgine J, Debruyne D (2014). "Emerging drugs of abuse: current perspectives on substituted cathinones". Substance Abuse and Rehabilitation. 5: 37–52. doi:10.2147/SAR.S37257. PMC 4043811. PMID 24966713.
  3. Simmons SJ, Leyrer-Jackson JM, Oliver CF, Hicks C, Muschamp JW, Rawls SM, Olive MF (October 2018). "DARK Classics in Chemical Neuroscience: Cathinone-Derived Psychostimulants". ACS Chemical Neuroscience. 9 (10): 2379–2394. doi:10.1021/acschemneuro.8b00147. PMC 6197900. PMID 29714473.
  4. Beck O, Bäckberg M, Signell P, Helander A (April 2018). "Intoxications in the STRIDA project involving a panorama of psychostimulant pyrovalerone derivatives, MDPV copycats". Clinical Toxicology. 56 (4): 256–263. doi:10.1080/15563650.2017.1370097. PMID 28895757. S2CID 3401681.
  5. Majchrzak M, Celiński R, Kuś P, Kowalska T, Sajewicz M (2018). "The newest cathinone derivatives as designer drugs: an analytical and toxicological review". Forensic Toxicology. 36 (1): 33–50. doi:10.1007/s11419-017-0385-6. PMC 5754390. PMID 29367861.
  6. Colzato LS, Ruiz MJ, van den Wildenberg WP, Hommel B (2011). "Khat use is associated with impaired working memory and cognitive flexibility". PLOS One. 6 (6): e20602. Bibcode:2011PLoSO...620602C. doi:10.1371/journal.pone.0020602. PMC 3115937. PMID 21698275.
  7. Europol 2008 Annual Report on the implementation of Council Decision 2005/387/JHA
  8. Europol 2009 Annual Report on the implementation of Council Decision 2005/387/JHA
  9. Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA
  10. Europol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA
  11. Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA
  12. Europol 2013 Annual Report on the implementation of Council Decision 2005/387/JHA
  13. Europol 2014 Annual Report on the implementation of Council Decision 2005/387/JHA
  14. Europol 2015 Annual Report on the implementation of Council Decision 2005/387/JHA
  15. Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA
  16. Europol 2017 Annual Report on the implementation of Council Decision 2005/387/JHA
  17. European Monitoring Center for Drugs and Drug Addiction (December 2020). New psychoactive substances: global markets, glocal threats and the COVID-19 pandemic. An update from the EU Early Warning System (PDF). Luxembourg: Publications Office of the European Union. doi:10.2810/921262. ISBN 9789294975584.
  18. Maurer HH, Kraemer T, Springer D, Staack RF (April 2004). "Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis". Therapeutic Drug Monitoring. 26 (2): 127–31. doi:10.1097/00007691-200404000-00007. PMID 15228152. S2CID 9255084.
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