Substituted cathinone

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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. Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug.[1]

Chemical derivatives[edit]

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:

Compound R1 R2 R3 R4
Cathinone H Me H H
Methcathinone H Me H Me
Ethcathinone H Me H Et
Buphedrone H Et H Me
NEB H Et H Et
NEP H nPr H Et
Pentedrone H nPr H Me
Dimethylcathinone H Me Me Me
Diethylpropion H Me Et Et
Bupropion 3-Cl Me H t-Bu
Mephedrone 4-Me Me H Me
3-MMC 3-Me Me H Me
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
4-EEC 4-Et Me H Et
Benzedrone 4-Me Me H Bn
2'-MeO-Benzedrone 4-Me Me H 2-MeO-Bn
4-MEC 4-Me Me H Et
N,N-DMMC 4-Me Me Me Me
N,N-MEMC 4-Me Me Me Et
N,N-DEMC 4-Me Me Et Et
EDMC 4-Et Me Me Me
2,4-DMMC 2,4-dimethyl Me H Me
3,4-DMMC 3,4-dimethyl Me H Me
DMEC 3,4-dimethyl Me H Et
2,4,5-TMMC 2,4,5-trimethyl Me H Me
Methedrone 4-MeO Me H Me
Ethedrone 4-MeO Me H Et
3-MOMC 3-MeO Me H Me
2-FMC 2-F Me H Me
2-FEC 2-F Me H Et
3-FMC 3-F Me H Me
3-FEC 3-F Me H Et
3-CMC 3-Cl Me H Me
3-BMC 3-Br Me H Me
Flephedrone 4-F Me H Me
4-FEC 4-F Me H Et
4-CMC 4-Cl Me H Me
Brephedrone 4-Br Me H Me
FMMC 3-F-4-Me Me H Me
3,5-DCMC 3,5-diCl Me H Me
3,5-DFMC 3,5-diF Me H Me
2,5-DMOMC 2,5-dimethoxy Me H Me
bk-MDOM 2,5-dimethoxy-4-methyl Me H Me
bk-MDA 3,4-methylenedioxy Me H H
2,3-MDMC 2,3-methylenedioxy Me H Me
Methylone 3,4-methylenedioxy Me H Me
Ethylone 3,4-methylenedioxy Me H Et
BMDP 3,4-methylenedioxy Me H Bn
3,4-EDMC 3,4-ethylenedioxy Me H Me
bk-IMP 3,4-trimethylene Me H Me
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
4-Me-NEB 4-Me Et H Et
4-Methoxybuphedrone 4-MeO Et H Me
Butylone 3,4-methylenedioxy Et H Me
Eutylone 3,4-methylenedioxy Et H Et
bk-PBDB 3,4-methylenedioxy Et H nPr
Bn-4-MeMABP 4-Me Et H Bn
BMDB 3,4-methylenedioxy Et H Bn
bk-DMBDB 3,4-methylenedioxy Et Me Me
5-Methylmethylone 3,4-methylenedioxy-5-Me Me H Me
5-Methylethylone 3,4-methylenedioxy-5-Me Me H Et
2-Methylbutylone 2-Me-3,4-methylenedioxy Et H Me
5-Methylbutylone 3,4-methylenedioxy-5-Me Et H Me
Pentylone 3,4-methylenedioxy nPr H Me
MMP 4-Me nPr H Me
MEP 4-Me nPr H Et
4-F-Pentedrone 4-F nPr H Me
DL-4662 3,4-diMeO nPr H Et
"NRG-3" β-naphthyl instead of phenyl Me H Me
bk-Methiopropamine thiophen-2-yl instead of phenyl Me H Me
bk-5-MAPB benzofuran-5-yl instead of phenyl Me H Me
bk-6-MAPB benzofuran-6-yl instead of phenyl Me H Me
α-Phthalimidopropiophenone H Me phthalimido
α-PPP H Me pyrrolidinyl
α-PBP H Et pyrrolidinyl
PPBO H Et piperidinyl
α-PVP (O-2387) H nPr pyrrolidinyl
α-PHP H nBu pyrrolidinyl
α-PEP H nPe pyrrolidinyl
4-MePPP 4-Me Me pyrrolidinyl
MOPPP 4-MeO Me pyrrolidinyl
3-F-PPP 3-F Me pyrrolidinyl
FPPP 4-F Me pyrrolidinyl
MPBP 4-Me Et pyrrolidinyl
FPBP 4-F Et pyrrolidinyl
3-MPBP 3-Me Et pyrrolidinyl
3-F-PBP 3-F Et pyrrolidinyl
EPBP 4-Et Et pyrrolidinyl
MOPBP 4-MeO Et pyrrolidinyl
O-2384 3,4-dichloro Et pyrrolidinyl
Pyrovalerone (O-2371) 4-Me nPr pyrrolidinyl
MPHP 4-Me nBu pyrrolidinyl
MPEP 4-Me pentyl pyrrolidinyl
MDPPP 3,4-methylenedioxy Me pyrrolidinyl
MDMPP 3,4-methylenedioxy α,α-di-Me pyrrolidinyl
MDPBP 3,4-methylenedioxy Et pyrrolidinyl
MDPV 3,4-methylenedioxy nPr pyrrolidinyl
5-Me-MDPV 3,4-methylenedioxy-5-Me nPr pyrrolidinyl
FPVP 4-F nPr pyrrolidinyl
MOPVP 4-MeO nPr pyrrolidinyl
DMPVP 3,4-dimethoxy nPr pyrrolidinyl
O-2390 3,4-dichloro nPr pyrrolidinyl
O-2494 4-Me iBu pyrrolidinyl
4F-PV8 4-F hexyl pyrrolidinyl
4F-PV9 4-F heptyl pyrrolidinyl
4-MeO-PV9 4-MeO heptyl pyrrolidinyl
Naphyrone (O-2482) β-naphthyl instead of phenyl nPr pyrrolidinyl
α-Naphyrone α-naphthyl instead of phenyl nPr pyrrolidinyl
α-PBT thiophen-2-yl instead of phenyl Et pyrrolidinyl
α-PVT thiophen-2-yl instead of phenyl nPr pyrrolidinyl

Legality[edit]

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.[2]

"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, 2nd April 2010

This text was added as an amendment to the Misuse of Drugs Act 1971, to come into force on 16 April 2010.[3] 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,[4][5] along with a further broad based structure ban even more expansive than the last.[6][7]

“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, 13th 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.[8]

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.[9]

See also[edit]

References[edit]

  1. ^ Colzato LS, Ruiz MJ, van den Wildenberg WP, Hommel B. Khat use is associated with impaired working memory and cognitive flexibility. PLoS One. 2011;6(6):e20602. PMID 21698275. Retrieved 2011-07-17.
  2. ^ Advisory Council on the Misuse of Drugs (UK). Consideration of the cathinones. 31 March 2010. Retrieved 2011-07-17.
  3. ^ "The Misuse of Drugs (Amendment) (England, Wales and Scotland) Regulations 2010 No. 1144". Opsi.gov.uk. Retrieved 2010-04-08. 
  4. ^ "NRG-1 'legal high' drug is banned". BBC News. 2010-07-12. Retrieved 2010-07-17. 
  5. ^ "Advisory Council on the Misuse of Drugs Naphyrone Report (2010)". Home Office. 2010-07-07. Retrieved 2010-07-17. 
  6. ^ "Explanatory Memorandum To The Misuse of Drugs (Amendment No. 2) (England, Wales and Scotland) Regulations 2010 No. 1799". Opsi.gov.uk. Retrieved 2010-07-18. 
  7. ^ "The Misuse of Drugs (Amendment No. 2) (England, Wales and Scotland) Regulations 2010 No. 1799". Opsi.gov.uk. Retrieved 2010-07-18. 
  8. ^ 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.
  9. ^ Goodnough A, Zezima K. An Alarming New Stimulant, Legal in Many States. New York Times 2011 July 16. Retrieved 2011-07-17.