Substituted cathinone

Cathinone

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

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]

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]

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-CBP)	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-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-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-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
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
BMDP	3,4-methylenedioxy	Me	H	Bn	1823274-68-5
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
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
3-F-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
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
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
α-Phthalimidopropiophenone	H	Me	phthalimido		19437-20-8
PPPO	H	Me	piperidinyl
PPBO	H	Et	piperidinyl		92728-82-0
FPPVO	4-F	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 (A-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
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
Pyrovalerone (O-2371)	4-Me	nPr	pyrrolidinyl		3563-49-3
4-Et-PVP	4-Et	nPr	pyrrolidinyl
3-F-PVP	3-F	nPr	pyrrolidinyl
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
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
FPHP	4-F	nBu	pyrrolidinyl		2230706-09-7
4-Cl-PHP	4-Cl	nBu	pyrrolidinyl
DMOPHP	3,4-dimethoxy	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
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
5-PPDI	3,4-trimethylene	Et	pyrrolidinyl
5-BPDI	3,4-trimethylene	nPr	pyrrolidinyl
5-HPDI	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[]

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.^[23]

"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.^[24] 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,^[25]^[26] along with a further broad based structure ban even more expansive than the last.^[27]^[28]

“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.^[29]

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.^[30]

References[]

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ Europol 2008 Annual Report on the implementation of Council Decision 2005/387/JHA
^ Europol 2009 Annual Report on the implementation of Council Decision 2005/387/JHA
^ Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA
^ Europol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA
^ Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA
^ Europol 2013 Annual Report on the implementation of Council Decision 2005/387/JHA
^ Europol 2014 Annual Report on the implementation of Council Decision 2005/387/JHA
^ Europol 2015 Annual Report on the implementation of Council Decision 2005/387/JHA
^ Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA
^ Europol 2017 Annual Report on the implementation of Council Decision 2005/387/JHA
^ 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.
^ Davis S, Rands-Trevor K, Boyd S, Edirisinghe M (April 2012). "The characterisation of two halogenated cathinone analogues: 3,5-difluoromethcathinone and 3,5-dichloromethcathinone". Forensic Science International. 217 (1–3): 139–45. doi:10.1016/j.forsciint.2011.10.042. PMID 22088945.
^ Błażewicz A, Bednarek E, Popławska M, Olech N, Sitkowski J, Kozerski L (2019). "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. doi:10.1007/s11419-018-00463-w. S2CID 59618061.
^ Westphal F, Girreser U, Angerer V, Auwärter V (January 2016). "Analytische Daten neuer 2-aminosubstituierter Methylendioxyvalerophenonderivate". Toxichem Krimtech. 83 (1): 3–29.
^ Lajtai A, et al. New psychoactive versus conventional stimulants - a ten-year review of casework in Hungary. Legal Medicine 2020; 47: 101780. doi:10.1016/j.legalmed.2020.101780
^ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" [Government Decree on Psychoactive Substances Banned from the Consumer Market]. Finlex Data Bank (in Finnish).
^ Advisory Council on the Misuse of Drugs (UK). Consideration of the cathinones. 31 March 2010. Archived 22 September 2011 at the Wayback Machine Retrieved 2011-07-17.
^ "The Misuse of Drugs (Amendment) (England, Wales and Scotland) Regulations 2010 No. 1144". Opsi.gov.uk. Retrieved 8 April 2010.
^ "NRG-1 'legal high' drug is banned". BBC News. 12 July 2010. Retrieved 17 July 2010.
^ "Advisory Council on the Misuse of Drugs Naphyrone Report (2010)". Home Office. 7 July 2010. Archived from the original on 17 July 2010. Retrieved 17 July 2010.
^ "Explanatory Memorandum To The Misuse of Drugs (Amendment No. 2) (England, Wales and Scotland) Regulations 2010 No. 1799" (PDF). Opsi.gov.uk. Retrieved 18 July 2010.
^ "The Misuse of Drugs (Amendment No. 2) (England, Wales and Scotland) Regulations 2010 No. 1799" (PDF). Opsi.gov.uk. Retrieved 18 July 2010.
^ 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.
^ Goodnough A, Zezima K (16 July 2011). "An Alarming New Stimulant, Legal in Many States". The New York Times. Retrieved 17 July 2011.

[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.

[pmid21698275-6] 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] 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.

[18] Davis S, Rands-Trevor K, Boyd S, Edirisinghe M (April 2012). "The characterisation of two halogenated cathinone analogues: 3,5-difluoromethcathinone and 3,5-dichloromethcathinone". Forensic Science International. 217 (1–3): 139–45. doi:10.1016/j.forsciint.2011.10.042. PMID 22088945.

[19] Błażewicz A, Bednarek E, Popławska M, Olech N, Sitkowski J, Kozerski L (2019). "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. doi:10.1007/s11419-018-00463-w. S2CID 59618061.

[20] Westphal F, Girreser U, Angerer V, Auwärter V (January 2016). "Analytische Daten neuer 2-aminosubstituierter Methylendioxyvalerophenonderivate". Toxichem Krimtech. 83 (1): 3–29.

[21] Lajtai A, et al. New psychoactive versus conventional stimulants - a ten-year review of casework in Hungary. Legal Medicine 2020; 47: 101780. doi:10.1016/j.legalmed.2020.101780

[22] "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" [Government Decree on Psychoactive Substances Banned from the Consumer Market]. Finlex Data Bank (in Finnish).

[ACMD2010-23] Advisory Council on the Misuse of Drugs (UK). Consideration of the cathinones. 31 March 2010. Archived 22 September 2011 at the Wayback Machine Retrieved 2011-07-17.

[24] "The Misuse of Drugs (Amendment) (England, Wales and Scotland) Regulations 2010 No. 1144". Opsi.gov.uk. Retrieved 8 April 2010.

[25] "NRG-1 'legal high' drug is banned". BBC News. 12 July 2010. Retrieved 17 July 2010.

[26] "Advisory Council on the Misuse of Drugs Naphyrone Report (2010)". Home Office. 7 July 2010. Archived from the original on 17 July 2010. Retrieved 17 July 2010.

[27] "Explanatory Memorandum To The Misuse of Drugs (Amendment No. 2) (England, Wales and Scotland) Regulations 2010 No. 1799" (PDF). Opsi.gov.uk. Retrieved 18 July 2010.

[28] "The Misuse of Drugs (Amendment No. 2) (England, Wales and Scotland) Regulations 2010 No. 1799" (PDF). Opsi.gov.uk. Retrieved 18 July 2010.

[29] 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.

[30] Goodnough A, Zezima K (16 July 2011). "An Alarming New Stimulant, Legal in Many States". The New York Times. Retrieved 17 July 2011.

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show v t Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-C 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-O 2C-O-4 2C-P 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-19 2C-T-21 2C-T-28 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

Substituted cathinone

Contents

List of substituted cathinones[]

Legality[]

See also[]

References[]