Substituted cathinone

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]

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
	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
	Hexedrone	H	nBu	H	Me
	Ethyl-Hexedrone	H	nBu	H	Et	18410-62-3
	N-Butyl-hexedrone	H	nBu	H	nBu
	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
	2-MEC	2-Me	Me	H	Et
	2-EEC	2-Et	Me	H	Et
	3-MMC	3-Me	Me	H	Me	1246816-62-5
	3-MEC	3-Me	Me	H	Et
	3-EMC	3-Et	Me	H	Me
	3-EEC	3-Et	Me	H	Et
	4-EMC	4-Et	Me	H	Me	1225622-14-9
	4-EEC	4-Et	Me	H	Et
	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
	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
	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
	2,4-DMMC	2,4-dimethyl	Me	H	Me
	2,4-DMEC	2,4-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
	2,4,5-TMMC	2,4,5-trimethyl	Me	H	Me
	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
	3-FC	3-F	Me	H	H
	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
	3-BMC	3-Br	Me	H	Me
	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
	4-CEC	4-Cl	Me	H	Et
	4-CiPC	4-Cl	Me	H	iPr
	4-CBC	4-Cl	Me	H	nBu
	4-CDMC	4-Cl	Me	Me	Me
	Brephedrone	4-Br	Me	H	Me	486459-03-4
	4-BEC	4-Br	Me	H	Et
	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
	MFMC	3-Me-4-F	Me	H	Me
	MMOMC	3-Me-4-MeO	Me	H	Me
	3,4-DCMC	3,4-dichloro	Me	H	Me
	3,5-DCMC	3,5-dichloro	Me	H	Me
	3,5-DFMC	3,5-difluoro	Me	H	Me
	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
	Methylone	3,4-methylenedioxy	Me	H	Me	186028-79-5
	Dimethylone	3,4-methylenedioxy	Me	Me	Me
	N-acetyl-methylone	3,4-methylenedioxy	Me	acetyl	Me
	N-hydroxy-methylone	3,4-methylenedioxy	Me	hydroxy	Me
	Ethylone	3,4-methylenedioxy	Me	H	Et	1112937-64-0
	Diethylone	3,4-methylenedioxy	Me	Et	Et
	N-acetyl-ethylone	3,4-methylenedioxy	Me	acetyl	Et
	N-isopropyl-βk-MDA	3,4-methylenedioxy	Me	H	iPr
	MDPT	3,4-methylenedioxy	Me	H	t-Bu
	BMDP	3,4-methylenedioxy	Me	H	Bn
	3,4-EDMC	3,4-ethylenedioxy	Me	H	Me
	βk-IMP	3,4-trimethylene	Me	H	Me
	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
	4-Bromobuphedrone	4-Br	Et	H	Me
	4-MeMABP	4-Me	Et	H	Me	1336911-98-8
	4-Me-NEB	4-Me	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
	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
	Dipentylone	3,4-methylenedioxy	nPr	Me	Me
	Hexylone	3,4-methylenedioxy	nBu	H	Me
	N-Ethylhexylone	3,4-methylenedioxy	nBu	H	Et
	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
	4-F-Pentedrone	4-F	nPr	H	Me
	4-Cl-Pentedrone	4-Cl	nPr	H	Me
	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
	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
	"NRG-3"	β-naphthyl instead of phenyl	Me	H	Me
	βk-Methiopropamine	thiophen-2-yl instead of phenyl	Me	H	Me	24065-17-6
	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
	α-Phthalimidopropiophenone	H	Me	phthalimido		19437-20-8
	PPPO	H	Me	piperidinyl
	PPBO	H	Et	piperidinyl
	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
	3-MePPP	3-Me	Me	pyrrolidinyl		1214940-01-8
	4-MePPP	4-Me	Me	pyrrolidinyl		1313393-58-6
	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
	2,4-DMPPP	2,4-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
	Pyrovalerone (O-2371)	4-Me	nPr	pyrrolidinyl		3563-49-3
	3-F-PVP	3-F	nPr	pyrrolidinyl
	FPVP	4-F	nPr	pyrrolidinyl		850352-31-7
	4-Cl-PVP	4-Cl	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
	FPHP	4-F	nBu	pyrrolidinyl
	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
	MDPEP (MD-PV8)	3,4-methylenedioxy	pentyl	pyrrolidinyl
	MDPOP (MD-PV9)	3,4-methylenedioxy	hexyl	pyrrolidinyl
	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-PVP	3,4-tetramethylene	nPr	pyrrolidinyl
	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

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.[21]

"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.[22] 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,[23][24] along with a further broad based structure ban even more expansive than the last.[25][26]

“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.[27]

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.[28]

• Markush structure
• Substituted amphetamines
• Substituted methylenedioxyphenethylamines
• Substituted phenethylamines
• Substituted phenylmorpholines
• Structural scheduling of synthetic cannabinoids
• Arylcyclohexylamines
• List of aminorex analogues
• List of fentanyl analogues
• List of methylphenidate analogues