Emerging drugs of abuse: current perspectives on substituted cathinones

Figures & data

Figure 1 Chemical structure of synthetic cathinones.

Table 1 List of the most common substituted cathinones

Usual names	Chemical name
Amfepramone or diethylpropion	2-diethylamino-1-phenyl-1-propanone
Benzedrone or methylbenzylcathinone or 4-MBC	1-(4-methylphenyl)-2-benzylamino-1-propanone
BMDB	2-benzylamino-1-(3,4-methylenedioxyphenyl)-1-butanone
BMDP or 3,4-MDBC	2-benzylamino-1-(3,4-methylenedioxyphenyl)-1-propanone
Brephedrone or 4-bromomethcathinone or 4-BMC	1-(4-bromophenyl)-2-(methylamino)-1-propanone
Buphedrone	2-(methylamino)-1-phenyl-1-butanone
Bupropion	1-(3-chlorophenyl)-2-(tertbutylamino)-1-propanone
Butylone or bk-MBDB	2-(methylamino)-1-(3,4-methylenedioxyphenyl)-1-butanone
Cathinone	2-amino-1-phenyl-1-propanone
Dibutylone or methylbutylone or bk-DMBDB	2-(dimethylamino)-1-(3,4-methylenedioxyphenyl)-1-butanone
Dimethylone or bk-MDDMA	1-(1,3-benzodioxol-5-yl)-2-(dimethylamino)-1-butanone
Dimethylmethcathinone or 3,4-DMMC	1-(3,4-dimethylphenyl)-2-(methylamino)-1-propanone
Ephedrone or methcathinone	2-(methylamino)-1-(4ethylphenyl)-1-propanone
Ethylbuphedrone or NEB	2-(ethylamino)-1-phenyl-1-butanone
Ethylcathinone or ethcathinone or ethylpropion	2-(ethylamino)-1-phenyl-1-propanone
Ethylmethcathinone or 4-EMC	2-(methylamino)-1-phenyl-1-propanone
Ethylone or bk-MDEA	2-(ethylamino)-1-(3,4-methylenedioxyphenyl)-1-propanone
Eutylone ou bk-EBDB	1-(1,3-benzodioxol-5-yl)-2-(ethylamino)-1-butanone
Flephedrone or 4-fluoromethcathinone or 4-FMC	2-(methylamino)-1-(4-fluorophenyl)-1-propanone
Fluorocathinone or ‘-FC	2-amino-1-(4-fluorophenyl)-1-propanone
Fluoromethcathinone or 3-FMC	2-(methylamino)-1-(3-fluorophenyl)-1-propanone
Isoethcathinone	2-(ethylamino)-1-phenyl-2-propanone
Isopentedrone	2-(methylamino)-1-phenyl-2-pentanone
MDMPP	1-(3,4-methylenedioxyphenyl)-2-methyl-2-pyrrolidinyl-1-propanone
MDPBP	1-(3,4-methylenedioxyphenyl)-2-(1-pyrrolidinyl)-1-butanone
MDPPP	1-(3,4-methylenedioxyphenyl)-2-(1-pyrrolidinyl)-1-propanone
MDPV or MDPK	1-(3,4-methylenedioxyphenol)-2-pyrrolidinyl-1-pentanone
Mephedrone or 4-methylmethcathinone or 4-MMC	2-(methylamino)-1-(4-methylphenyl)-1-propanone
Metamfepramone or dimethylcathinone or dimethylpropion	2-dimethylamino-1-phenyl-1-propanone
Methedrone or 4-methoxymethcathinone or bk-PMMA	1-(4-methoxyphenyl)-2-(methylamino)-1-propanone
Methylbuphedrone or 4Me-MABP or bk-N-methyl-4-MAB	2-(methyllamino)-1-(4-methylphenyl)-1-butanone
Methylethcathinone or 4-MEC	2-(ethylamino)-1-(4-methylphenyl)-1-propanone
Methylmethcathinone or 3-MMC	2-(methylamino)-1-(3-methylphenyl)-1-propanone
Methylone or MDMC or bk-MDMA	2-methylamino-1-[3,4-methylenedioxyphenyl]-1-propanone
MOPPP	4′-methoxy-α-pyrrolidinovalerophenone
MPBP	1-(4-methylphenyl)-2-(1-pyrrolidinyl)-1-butanone
MPHP	4′-methyl-α-pyrrolidinovalerophenone
MPPP	4′-methyl-α-pyrrolidinovalerophenone
Naphyrone	1-naphthalen-2-yl-2-pyrrolidin-1-yl-1-pentanone
Propylbutylone or bk-PBDB	2-(propylamino)-1-(3,4-methylenedioxyphenyl)-1-butanone
Pentedrone or ethyl-methcathinone	2-(methylamino)-1-phenyl-1-pentanone
Pentylone	2-(methylamino)-1-(3,4-methylenedioxyphenyl)-1-pentanone
PBP	1-phenyl-2-(1-pyrrolidinyl)-1-butanone
PEP	1-phenyl-2-(1-pyrrolidinyl)-1-heptanone
PPP	1-phenyl-2-(1-pyrrolidinyl)-1-propanone
PVP	1-phenyl-2-(1-pyrrolidinyl)-1-pentanone
Pyrovalerone	11-(4-methylphenyl)-2-(1-pyrrolidinyl)-1-pentanone
Trimethylmethcathinone or 2,4,5-TMMC	2-(methylamino)-1-(2,4,5-trimethylphenyl)-1-propanone

Table 2 Related structure of several alkylcathinones

Abbreviations: MMC, mehylmethcathinone; TMMC, trimethylmethcathinone; EMC, ethylmethcathinone; MEC, methylethcathinone; NEB, ethylbuphedrone.

Table 3 Structure of pyrrolidinyl substituted cathinones

Abbreviations: PPP, pyrrolidinopropiophenone; PBP, pyrrolidinobutyrophenone; PVP, pyrrolidinovalerophenone; PEP, pyrrolidinoenanthophenone; MPPP, methyl pyrrolidinopropiophenone; MOPPP, methoxy pyrrolidinopropiophenone; MDPBP, methylenedioxy pyrrolidinobutyrophenone; MDPV, methylenedioxypyrovalerone; MDMPP, methylenedioxy pyrrolidinopropiophenone.

Table 4 Chemical structure of methylenedioxy amphetamines and cathinones

Abbreviations: MDMA, methylenedioxymethylamphetamine; MDEA, methylenedioxyethylamphetamine; MBDB, methylbenzodioxolylbutanamine; MBDP, methylbenzo-dioxolylpentanamine; EBDB, ethylbenzodioxolylbutanamine; MMBDB, dimethylbenzodioxolylbutanamine.

Table 5 Gas-chromatography mass spectrometry identification of substituted cathinones

Name	Molecular formula	GC-MS identification (electronic impact)		Reference
		Base peak	Other peaks
Amfepramone	C13H19NO	100	44, 72, 206	*
Benzedrone	C17H19NO	91	119, 146, 236	*
BMDB	C18H19NO3	91	65, 121, 148	*
BMDP	C17H17NO3	91	65, 134	*
Brephedrone	C10H12BrNO	58	155, 183, 75	*
Buphedrone	C11H15NO	72	77, 105	^Citation20
Bupropion	C13H18CINO	44	75, 100, 139	*
Butylone	C12H15NO3	72	121, 149	^Citation6
Cathinone	C9H11NO	44	51, 77, 105	*
Dibutylone	C13H17NO3	86	121, 149	*
Dimethylmethcathinone	C12H17NO	58	77, 105, 133	*
Dimethylone	C12H15NO3	72	91, 121, 149	^Citation96
Ephedrone	C10H13NO	58	51, 56, 77	*
Ethcathinone	C11H15NO	72	44, 105	^Citation5
Ethylbuphedrone	C12H17NO	86	77,105	*
Ethylone	C12H15NO3	72	121, 149, 44	^Citation96
Eutylone	C13H17NO3	72	91, 121, 149	*
Flephedrone	C10H12FNO	58	75, 95, 123, 182	^Citation97
3-FMC	C10H12FNO	58	75, 95, 123	^Citation97
MDPBP	C15H19NO3	112	149	^Citation98
MDPPP	C14H17NO3	98	121, 149, 178	^Citation99
MDPV	C16H21NO3	126	149	^Citation6
4-MEC	C12H17NO	72	119, 91	^Citation100
Mephedrone	C11H15NO	58	91, 119, 162	^Citation5
Metamfepramone	C11H15NO	72	51, 56, 70, 77	*
Methedrone	C11H15NO2	58	77, 135	^Citation101
Methylbuphedrone	C12H17NO	72	91, 119, 57	*
Methylethcathinone	C12H17NO	72	44, 91, 119	*
Methylone	C11H13NO3	58	91, 121, 149	^Citation6
MOPPP	C14H19NO2	98	107, 135, 233	^Citation99
MPBP	C15H21NO	112	119,91	^Citation102
MPHP	C17H25NO	140		^Citation77
MPPP	C14H19NO	98	56, 91, 119, 216	^Citation72
Naphyrone	C19H23NO	126	84, 155	^Citation103
NEB	C12H17NO	86	77, 58, 105	*
PBP	C14H19NO	112	77	^Citation80
Pentedrone	C12H17NO	86	44, 77, 105	^Citation104
Pentylone	C13H17NO3	86	44, 149	^Citation104
PPP	C13H17NO	98	56, 77, 105	^Citation72
PVP	C15H21NO	126	77, 84, 232	*
Pyrovalerone	C16H23NO	126	91, 119, 135	*

Note:

* Personal data.

Abbreviations: BMDB, benzylaminomethylenedioxyphenylbutanone; BMDP, benzylaminomethylenedioxyphenylpropanone; FMC, fluoromethcathinone; MDPBP, methy-lenedioxypyrrolidinobutyrophenone; MDPPP, methylenedioxypyrrolidinopropiophenone; MDPV, methylenedioxypyrovalerone; MEC, methylethcathinone; MOPPP, methoxy pyrrolidinopropiophenone; MPBP, methylpyrrolidinobutyrophenone; MPHP, methylpyrrolidinohexanophenone; MPPP, methylpyrrolidinopropiophenone; NEB, ethylbuphedrone; PBP, pyrrolidinobutyrophenone; PPP, α-pyrrolidinopropiophenone; PVP, α-pyrrolidinovalerophenone.

Table 6 Liquid chromatography–tandem mass spectrometry identification of substituted cathinones

Name	Molecular formula	Molecular weight	Multiple reaction monitoring (MRM) transitions		Reference
			Precursor ion [m/z]	Product ion [m/z]
Amfepramone	C13H19NO	205,30	206,1	105; 133; 100,1; 72	^Citation19
BMDB	C18H19NO3	297,30	298,1	280,13; 250,1; 191; 148	*
BMDP	C17H17NO3	283,30	284,1	266,1; 236,1;134,1	*
Buphedrone	C11H15NO	177,24	178,1	160,1; 91,1; 77,1	^Citation20
Bupropion	C13H18CINO	239,74	240	185	^Citation18
Butylone	C12H15NO3	221,25	222	174; 204,3; 191; 161	^Citation19
Cathinone	C9H11NO	149,19	150	132,1; 117,2	^Citation24
Dibutylone	C13H17NO3	235,28	236,1	191,04; 161,05; 86,36	*
Dimethylcathinone	C11H15NO	177,24	178,1	105,1; 133,1	^Citation11
Dimethylmethcathinone	C12H17NO	191,27	192,05	174; 159, 158	^Citation24
Ephedrone	C10H13NO	163,22	164,2	146,1; 131	^Citation24
Ethcathinone	C11H15NO	177,24	178,1	160; 132,1	^Citation24
Ethylone	C12H15NO3	221,25	222	174; 204,3	^Citation24
Flephedrone	C10H12FNO	181,21	182,2	164; 149	^Citation24
3-FMC	C10H12FNO	181,21	182,2	164; 149	^Citation24
MDPPP	C14H17NO3	247,28	248	98,1; 147	^Citation24
MDPV	C16H21NO3	275,35	276,2	126,1; 135,1; 149,9; 175,1	*
MDPBP	C15H19NO3	261,32	262,2	112,2; 149,1	^Citation11
Mephedrone	C11H15NO	177,24	178,2	160,2; 145; 143,9	^Citation24
Metamfepramone	C11H15NO	177,24	178,1	105,1; 77,1; 72,1	*
Methedrone	C11H15NO	193,24	194,1	175,9; 160,9; 146	^Citation24
Methylethcathinone	C12H17NO	191,27	192,2	174,3; 144,1; 91,1	^Citation24
Methylone	C11H13NO3	207,23	208	159,9; 190,2; 132,1	^Citation24
Naphyrone	C19H23NO	281,39	282,1	141,1; 211; 127,7	^Citation24
Pentedrone	C12H17NO	191,27	192,18	174,1; 132,2; 91,1	*
Pentylone	C13H17NO3	235,28	236,1	188; 218; 175	^Citation24
PPP	C13H17NO	203,28	204,1	105,1; 132,9; 98,2	^Citation24
PVP	C15H21NO	231,33	232,21	91,1; 77,1; 105,1; 126,1	*
Pyrovalerone	C16H23NO	245,36	246,1	105,1; 174,9; 91,1	^Citation24

Note:

* Personal data.

Abbreviations: BMDB, benzylaminomethylenedioxyphenylbutanone; BMDP, benzylaminomethylenedioxyphenylpropanone; FMC, fluoromethcathinone; MDPPP, methylene dioxypyrrolidinopropiophenone; MDPV, methylenedioxypyrovalerone; MDPBP, methylenedioxypyrrolidinobutyrophenone; PPP, α-pyrrolidinopropiophenone; PVP, α-pyrrolidinovalerophenone.

Table 7 Blood concentrations measured in several fatal cases

Substituted cathinone	Sex	Age (year)	Blood concentration (mg/L)	Reference
Butylone	Male	21	20	^Citation105
MDPV	Female	35	1.2	^Citation80
MDPV	Male	39	1.0	^Citation106
Mephedrone	Female	49	0.98	^Citation107
Mephedrone	Male	19	2.24	^Citation107
Methedrone	Male	23	8.4*	^Citation101
Methedrone	Male	19	9.6*	^Citation101
Methylone	Male	19	0.74	^Citation71
Methylone	Male	38	0.11	^Citation71
Methylone	Female	35	1.1	^Citation71
Methylone	Male	23	0.84; 1	^Citation108
Methylone	Female	19	3.3	^Citation108
Methylone	Male	23	0.58	^Citation108
Methylone	Male	19	0.7	^Citation109
Methylone	Male	16	0.227	^Citation57

Note:

* mg/kg.

Abbreviation: MDPV, methylenedioxypyrovalerone.

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