Substituted cathinone

Last updated March 31, 2024

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]^[23]^[24]^[25]^[26]^[27]^[28]

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-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
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^[29]	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
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
Pyrovalerone (O-2371)	4-Me	nPr	pyrrolidinyl		3563-49-3
4-Et-PVP	4-Et	nPr	pyrrolidinyl
3F-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
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
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.^[30]

"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.^[31] 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,^[32]^[33] along with a further broad based structure ban even more expansive than the last.^[34]^[35]

"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.

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.^[36]

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.^[37]

Related Research Articles

A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Designer drugs include psychoactive substances that have been designated by the European Union as new psychoactive substances (NPS) as well as analogs of performance-enhancing drugs such as designer steroids. Some of these were originally synthesized by academic or industrial researchers in an effort to discover more potent derivatives with fewer side effects and shorter duration and were later co-opted for recreational use. Other designer drugs were prepared for the first time in clandestine laboratories. Because the efficacy and safety of these substances have not been thoroughly evaluated in animal and human trials, the use of some of these drugs may result in unexpected side effects.

<span class="mw-page-title-main">Methylenedioxypyrovalerone</span> Chemical compound

Methylenedioxypyrovalerone (MDPV) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI). It was first developed in the 1960s by a team at Boehringer Ingelheim. Its activity at the dopamine transporter is six times stronger than at the norepinephrine transporter and it is virtually inactive at the serotonin transporter. MDPV remained an obscure stimulant until around 2004 when it was reportedly sold as a designer drug. In the US, products containing MDPV and labeled as bath salts were sold as recreational drugs in gas stations, similar to the marketing for Spice and K2 as incense, until it was banned in 2011.

Substituted phenethylamines are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents.

These drugs are known in the UK as controlled drug, because this is the term by which the act itself refers to them. In more general terms, however, many of these drugs are also controlled by the Medicines Act 1968, there are many other drugs which are controlled by the Medicines Act but not by the Misuse of Drugs Act, and some other drugs are controlled by other laws.

<i>alpha</i>-Pyrrolidinopentiophenone Chemical compound

α-Pyrrolidinopentiophenone is a synthetic stimulant of the cathinone class developed in the 1960s that has been sold as a designer drug and often consumed for recreational reasons. α-PVP is chemically related to pyrovalerone and is the ketone analog of prolintane.

<span class="mw-page-title-main">Naphyrone</span> Substituted cathinone stimulant drug

Naphyrone, also known as O-2482 and naphthylpyrovalerone, is a substituted cathinone drug derived from pyrovalerone that acts as a triple reuptake inhibitor, producing stimulant effects and has been reported as a novel designer drug. No safety or toxicity data is available on the drug.

Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).

<span class="mw-page-title-main">Cannabicyclohexanol</span> Chemical compound

Cannabicyclohexanol is a cannabinoid receptor agonist drug, developed by Pfizer in 1979. On 19 January 2009, the University of Freiburg in Germany announced that an analog of CP 47,497 was the main active ingredient in the herbal incense product Spice, specifically the 1,1-dimethyloctyl homologue of CP 47,497, which is now known as cannabicyclohexanol. The 1,1-dimethyloctyl homologue of CP 47,497 is in fact several times more potent than the parent compound, which is somewhat unexpected as the 1,1-dimethylheptyl is the most potent substituent in classical cannabinoid compounds such as HU-210.

<span class="mw-page-title-main">6-(2-Aminopropyl)indole</span> Chemical compound

6-(2-Aminopropyl)indole is an indole derivative which was first identified being sold on the designer drug market by a laboratory in the Czechia in July 2016.

<span class="mw-page-title-main">2-Fluorodeschloroketamine</span> Chemical compound

2-Fluorodeschloroketamine is a dissociative anesthetic related to ketamine. Its sale and use as a designer drug has been reported in various countries. It is an analogue of ketamine where the chlorine group has been replaced by fluorine. Due to its recent emergence, the pharmacological specifics of the compound are mostly unclear, but effects are reported to be similar to its parent compound, ketamine.

<i>N</i>-Ethylhexedrone Stimulant of the cathinone class

N-Ethylhexedrone (also known as α-ethylaminocaprophenone, N-ethylnorhexedrone, hexen, and NEH) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) with IC₅₀ values of 0.0978 and 0.0467 μM, respectively. N-Ethylhexedrone was first mentioned in a series of patents by Boehringer Ingelheim in the 1960s which led to the development of the better-known drug methylenedioxypyrovalerone (MDPV). Since the mid-2010s, N-ethylhexedrone has been sold online as a designer drug. In 2018, N-ethylhexedrone was the second most common drug of the cathinone class to be identified in Drug Enforcement Administration seizures.

To combat the illicit synthetic cannabinoid industry many jurisdictions have created a system to control these cannabinoids through their general structure as opposed to their specific identity. In this way new analogs are already controlled before they are even created. A large number of cannabinoids have been grouped into classes based on similarities in their chemical structure, and these classes have been widely adopted across a variety of jurisdictions.

Flunitrazolam is a triazolobenzodiazepine (TBZD), which are benzodiazepine (BZD) derivatives, that has been sold online as a designer drug, and is a potent hypnotic and sedative drug similar to related compounds such as flunitrazepam, clonazolam and flubromazolam. It was first definitively identified and reported to the EMCDDA Early Warning System, by an analytical laboratory in Germany in October 2016, and had not been described in the scientific or patent literature before this. It is the triazole analogue of Flunitrazepam (Rohypnol). The addition of the triazole ring to the scaffold increases potency significantly, this is evident as flunitrazolam is reported anecdotally to be active in the microgram level. It is active at 0.1 mg.

Isobutyrylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. It is believed to be around the same potency as butyrfentanyl but has been less widely distributed on illicit markets, though it was one of the earliest of the "new wave" of fentanyl derivatives to appear, and was reported in Europe for the first time in December 2012.

Difludiazepam (Ro07-4065) is a benzodiazepine derivative which is the 2',6'-difluoro derivative of fludiazepam. It was invented in the 1970s but was never marketed, and has been used as a research tool to help determine the shape and function of the GABA_A receptors, at which it has an IC₅₀ of 4.1nM. Difludiazepam has subsequently been sold as a designer drug, and was first notified to the EMCDDA by Swedish authorities in 2017.

α-PHiP is a stimulant drug of the cathinone class that has been sold online as a designer drug. It is a positional isomer of pyrovalerone, with the methyl group shifted from the 4-position of the aromatic ring to the 4-position of the acyl chain. In a classic 2006 study of pyrrolidinyl cathinone derivatives by Meltzer et al. at Organix, the alpha-isobutyl derivative of pyrovalerone, O-2494, was found to have the highest potency in vitro as an inhibitor of the dopamine transporter of the alpha substituted derivatives tested; however, it was not until ten years later in July 2016 that α-PHiP was first identified as a designer drug, when it was reported to the EMCDDA by a forensic laboratory in Slovenia.

<span class="mw-page-title-main">TH-PVP</span> Chemical compound

TH-PVP is a substituted cathinone derivative which has been sold as a designer drug. It was first identified by a forensic laboratory in Hungary in 2015, but has subsequently been found in numerous other countries around the world including Spain, Belgium, Poland, Turkey and Brazil. Pharmacological studies in vitro showed it to inhibit reuptake and promote the release of monoamine neurotransmitters with some selectivity for serotonin, but it failed to produce stimulant effects in animals, and has a pharmacological profile more comparable to that of sedating empathogens such as MDAI and 5-Methyl-MDA.

2-Methylmethcathinone (2-MMC), also known as ortomephedrone is a recreational designer drug with stimulant and euphoric effects. It is a substituted cathinone derivative, closely related to better known drugs such as 3-methylmethcathinone and 4-methylmethcathinone (mephedrone). It was first identified in Sweden in 2014, and has subsequently been reported in other European countries such as Poland and Spain.

<span class="mw-page-title-main">Dipentylone</span> Substituted cathinone stimulant drug

N,N-Dimethylpentylone is a substituted cathinone derivative with stimulant effects, which has been sold as a designer drug, first detected in Sweden in 2014.

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
↑ 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.
↑ 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.
↑ Liu C, Jia W, Li T, Hua Z, Qian Z (August 2017). "Identification and analytical characterization of nine synthetic cathinone derivatives N-ethylhexedrone, 4-Cl-pentedrone, 4-Cl-α-EAPP, propylone, N-ethylnorpentylone, 6-MeO-bk-MDMA, α-PiHP, 4-Cl-α-PHP, and 4-F-α-PHP". Drug Testing and Analysis. 9 (8): 1162–1171. doi:10.1002/dta.2136. PMID 27863142.
↑ 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.
↑ 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.
↑ Carlsson A, Sandgren V, Svensson S, Konradsson P, Dunne S, Josefsson M, Dahlén J (February 2018). "Prediction of designer drugs: Synthesis and spectroscopic analysis of synthetic cathinone analogs that may appear on the Swedish drug market". Drug Testing and Analysis. 10 (7): 1076–1098. doi:10.1002/dta.2366. PMID 29426062.
↑ Cheng WC, Wong WC (May 2019). "Forensic drug analysis of chloro-N,N-dimethylcathinone (CDC) and chloroethcathinone (CEC): Identification of 4-CDC and 4-CEC in drug seizures and differentiation from their ring-substituted positional isomers". Forensic Science International. 298: 268–277. doi:10.1016/j.forsciint.2019.03.002. PMID 30925345. S2CID 87589412.
↑ Lajtai A, Mayer M, Lakatos Á, Kuzma M, Miseta A (November 2020). "New psychoactive versus conventional stimulants - a ten-year review of casework in Hungary". Legal Medicine. 47: 101780. doi: 10.1016/j.legalmed.2020.101780 . PMID 32882537. S2CID 221496728.
↑ Jones NS, Comparin JH (2020). "Interpol review of controlled substances 2016-2019". Forensic Science International. Synergy. 2: 608–669. doi:10.1016/j.fsisyn.2020.01.019. PMC 7770462 . PMID 33385148.
↑ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" [Government Decree on Psychoactive Substances Banned from the Consumer Market]. Finlex Data Bank (in Finnish).
↑ Baggott M. Advantageous Tryptamine Compositions For Mental Disorders or Enhancement. Patent WO 2022/061242
↑ 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.

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[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] 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.

[19] 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.

[pmid27863142-20] Liu C, Jia W, Li T, Hua Z, Qian Z (August 2017). "Identification and analytical characterization of nine synthetic cathinone derivatives N-ethylhexedrone, 4-Cl-pentedrone, 4-Cl-α-EAPP, propylone, N-ethylnorpentylone, 6-MeO-bk-MDMA, α-PiHP, 4-Cl-α-PHP, and 4-F-α-PHP". Drug Testing and Analysis. 9 (8): 1162–1171. doi:10.1002/dta.2136. PMID 27863142.

[21] 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.

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

[pmid29367861-23] 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.

[pmid29426062-24] Carlsson A, Sandgren V, Svensson S, Konradsson P, Dunne S, Josefsson M, Dahlén J (February 2018). "Prediction of designer drugs: Synthesis and spectroscopic analysis of synthetic cathinone analogs that may appear on the Swedish drug market". Drug Testing and Analysis. 10 (7): 1076–1098. doi:10.1002/dta.2366. PMID 29426062.

[pmid30925345-25] Cheng WC, Wong WC (May 2019). "Forensic drug analysis of chloro-N,N-dimethylcathinone (CDC) and chloroethcathinone (CEC): Identification of 4-CDC and 4-CEC in drug seizures and differentiation from their ring-substituted positional isomers". Forensic Science International. 298: 268–277. doi:10.1016/j.forsciint.2019.03.002. PMID 30925345. S2CID 87589412.

[pmid32882537-26] Lajtai A, Mayer M, Lakatos Á, Kuzma M, Miseta A (November 2020). "New psychoactive versus conventional stimulants - a ten-year review of casework in Hungary". Legal Medicine. 47: 101780. doi: 10.1016/j.legalmed.2020.101780 . PMID 32882537. S2CID 221496728.

[pmid33385148-27] Jones NS, Comparin JH (2020). "Interpol review of controlled substances 2016-2019". Forensic Science International. Synergy. 2: 608–669. doi:10.1016/j.fsisyn.2020.01.019. PMC 7770462 . PMID 33385148.

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

[29] Baggott M. Advantageous Tryptamine Compositions For Mental Disorders or Enhancement. Patent WO 2022/061242

[ACMD2010-30] 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.

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

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

[33] "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.

[34] "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.

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

[36] 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.

[37] 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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v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 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-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 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

Related Research Articles

References