Substituted cathinone - AbsoluteAstronomy.com

Substituted cathinones, which include some stimulant

Stimulant

Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...

s and entactogen

Empathogen-entactogen

The terms empathogen and entactogen are used to describe a class of psychoactive drugs that produce distinctive emotional and social effects similar to those of MDMA. Putative members of this class include 2C-B, 2C-I, MDMA, MDA, MDEA, MBDB, 2C-T-7, and 2C-T-2, among others...

s, are derivatives of cathinone

Cathinone

Cathinone, or Benzoylethanamine, is a monoamine alkaloid found in the shrub Catha edulis and is chemically similar to ephedrine, cathine and other amphetamines. Cathinone induces the release of dopamine from striatal preparations that are prelabelled either with dopamine or its precursors. It is...

. They feature a phenethylamine

Phenethylamine

Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...

core with an alkyl group

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...

attached to the alpha carbon, and a ketone

Ketone

In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...

group attached to the beta carbon, along with additional substitution

Substitution reaction

In a substitution reaction, a functional group in a particular chemical compound is replaced by another group. In organic chemistry, the electrophilic and nucleophilic substitution reactions are of prime importance...

s. Cathinone occurs naturally in the plant khat

Khat

Khat, qat, gat or Waquish Spoken from true Yemeni, is a flowering plant native to tropical East Africa and the Arabian Peninsula....

whose leaves are chewed as a recreational drug.

Chemical derivatives

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 Cathinone Cathinone, or Benzoylethanamine, is a monoamine alkaloid found in the shrub Catha edulis and is chemically similar to ephedrine, cathine and other amphetamines. Cathinone induces the release of dopamine from striatal preparations that are prelabelled either with dopamine or its precursors. It is...	H	H	H	H Hydrogen Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
Methcathinone Methcathinone Methcathinone , is a psychoactive stimulant, sometimes used as a recreational drug and considered addictive. It is usually snorted, but can be smoked, injected, or taken orally...	H	H	H	Me
Ethcathinone Ethcathinone Ethcathinone, also known as ethylpropion, is a stimulant drug of the phenethylamine, amphetamine, and cathinone chemical classes. It is an active metabolite of the prodrug diethylcathinone and is fully responsible for its effects...	H	H	H	Et Ethyl Ethyl may refer to:* Ethyl group, a functional group in organic chemistry* Ethyl Corporation, a fuel additive company* Ethanol, also known as ethyl alcohol* Cold Ethyl, a rock band founded by Nicke Andersson...
Buphedrone	H	Me	H	Me
NEB	H	Me	H	Et
NEP	H	Et	H	Et
Pentedrone Pentedrone Pentedrone, also known as 2--1-phenylpentan-1-one or α-methylamino-valerophenone, is a designer drug with presumably stimulant effects, which has been found since 2010 as an ingredient in a number of "bath salt" mixes sold as legal highs....	H	Et	H	Me
Dimethylcathinone Dimethylcathinone Metamfepramone is a stimulant drug of the phenethylamine, and cathinone chemical classes...	H	H	Me	Me
Diethylpropion	H	H	Et	Et
Bupropion Bupropion Bupropion is an atypical antidepressant and smoking cessation aid. The drug is a non-tricyclic antidepressant and differs from most commonly prescribed antidepressants such as SSRIs, as its primary pharmacological action is thought to be norepinephrine-dopamine reuptake inhibition...	3-Cl	H	H	t-Bu
Mephedrone	4-Me	H	H	Me
3-MMC	3-Me	H	H	Me
4-EMC	4-Et	H	H	Me
4-EEC	4-Et	H	H	Et
Benzedrone Benzedrone Benzedrone is a designer drug with presumably stimulant effects, which has been found since 2010 as an ingredient in a number of "bath salt" mixes sold as legal highs....	4-Me	H	H	Bn Benzyl In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C6H5CH2-. Benzyl features a benzene ring attached to a CH2 group.-Nomenclature:...
4-MEC	4-Me	H	H	Et
N,N-DMMC	4-Me	H	Me	Me
N,N-DEMC	4-Me	H	Et	Et
3,4-DMMC 3,4-Dimethylmethcathinone 3,4-Dimethylmethcathinone is a stimulant drug first reported in 2010 as a designer drug analogue of mephedrone, apparently produced in response to the banning of mephedrone, following its widespread abuse in many countries in Europe and around the world.-See also:* Substituted cathinone*...	3,4-dimethyl	H	H	Me
Methedrone	4-MeO Methoxy In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether...	H	H	Me
Ethedrone	4-MeO Methoxy In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether...	H	H	Et
2-FMC	2-F	H	H	Me
3-FMC	3-F	H	H	Me
Flephedrone Flephedrone Flephedrone, also known as 4-fluoromethcathinone , is a stimulant drug of the cathinone chemical class.- History :Flephedrone started to be sold as a designer drug in 2008, along with its structural isomer 3-fluoromethcathinone .- Toxicity :Flephedrone has only a short history of human use and its...	4-F Fluorine Fluorine is the chemical element with atomic number 9, represented by the symbol F. It is the lightest element of the halogen column of the periodic table and has a single stable isotope, fluorine-19. At standard pressure and temperature, fluorine is a pale yellow gas composed of diatomic...	H	H	Me
Brephedrone	4-Br Bromine Bromine ") is a chemical element with the symbol Br, an atomic number of 35, and an atomic mass of 79.904. It is in the halogen element group. The element was isolated independently by two chemists, Carl Jacob Löwig and Antoine Jerome Balard, in 1825–1826...	H	H	Me
FMMC	3-F-4-Me	H	H	Me
bk-MDA	3,4-methylenedioxy	H	H	H
Methylone	3,4-methylenedioxy	H	H	Me
Ethylone	3,4-methylenedioxy	H	H	Et
BMDP	3,4-methylenedioxy	H	H	Bn
bk-IMP	3,4-trimethylene	H	H	Me
4-Fluorobuphedrone	4-F	Me	H	Me
4-MeMABP	4-Me	Me	H	Me
4-Methoxybuphedrone	4-MeO	Me	H	Me
Butylone	3,4-methylenedioxy	Me	H	Me
Eutylone Eutylone β-Keto-Ethylbenzodioxolylbutanamine is a stimulant compound developed in the 1960s, which has been reported as a novel designer drug.- See also :* Butylone* EBDB* Ethylone* MDEA* Pentylone...	3,4-methylenedioxy	Me	H	Et
BMDB	3,4-methylenedioxy	Me	H	Bn
bk-DMBDB	3,4-methylenedioxy	Me	Me	Me
5-Methylmethylone	3,4-methylenedioxy-5-Me	H	H	Me
2-Methylbutylone	2-Me-3,4-methylenedioxy	Me	H	Me
5-Methylbutylone	3,4-methylenedioxy-5-Me	Me	H	Me
Pentylone Pentylone β-Keto-Methylbenzodioxolylpentanamine is a stimulant compound developed in the 1960s, which has been reported as a novel designer drug, identified in some samples of powders sold as "NRG-1", along with varying blends of other substituted cathinone derivatives including flephedrone, MDPBP, MDPV and...	3,4-methylenedioxy	Et	H	Me
MEP	4-Me	Et	H	Et
bk-Methiopropamine Methiopropamine Methiopropamine is a thiophene-based structural analog of methamphetamine originally reported in 1942.It originally appeared for public sale in the UK in December 2010 as a "research chemical"...	thiophen-2-yl instead of phenyl	H	H	methyl
α-Phthalimidopropiophenone	H	H	phthalimido
α-PPP	H	H	pyrrolidinyl
α-PBP	H	Me	pyrrolidinyl
4-Et-α-PBP	4-Et	Me	pyrrolidinyl
4-MeO-α-PBP	4-MeO	Me	pyrrolidinyl
O-2384	3,4-dichloro	Me	pyrrolidinyl
α-PVP (O-2387)	H	Et	pyrrolidinyl
MPPP 4'-Methyl-α-pyrrolidinopropiophenone 4'-Methyl-α-pyrrolidinopropiophenone is a stimulant drug. It is very structurally similar to α-PPP, with only one added methyl group in the para position on the phenyl ring. MPPP was sold in Germany as a designer drug in the late 1990s and early 2000s, along with a number of other...	4-Me	H	pyrrolidinyl
MOPPP	4-MeO	H	pyrrolidinyl
MPBP	4-Me	Me	pyrrolidinyl
Pyrovalerone Pyrovalerone Pyrovalerone is a psychoactive drug with stimulant effects via acting as a norepinephrine-dopamine reuptake inhibitor , and is used for the clinical treatment of chronic fatigue or lethargy and as an anorectic or appetite suppressant for weight loss purposes... (O-2371)	4-Me	Et	pyrrolidinyl
MPHP	4-Me	Pr Propyl In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula -C3H7. It is the substituent form of the alkane propane...	pyrrolidinyl
MDPPP	3,4-methylenedioxy	H	pyrrolidinyl
MDPBP	3,4-methylenedioxy	Me	pyrrolidinyl
MDPV MDPV Methylenedioxypyrovalerone is a psychoactive drug with stimulant properties which acts as a norepinephrine-dopamine reuptake inhibitor . Reportedly, it has been sold since around 2004 as a designer drug. It is also known as MDPK, MTV, Magic, Maddie, Black Rob, Super Coke and PV...	3,4-methylenedioxy	Et	pyrrolidinyl
O-2390	3,4-dichloro	Et	pyrrolidinyl
O-2494	4-Me	iPr Isopropyl In organic chemistry, isopropyl is a propyl with a group attached to the secondary carbon. If viewed as a functional group an isopropyl is an organic compound with a propyl group attached at its secondary carbon.The bond is therefore on the middle carbon....	pyrrolidinyl
Naphyrone (O-2482)	β-naphthyl instead of phenyl	Et	pyrrolidinyl
α-PVT	thiophen-2-yl instead of phenyl	Et	pyrrolidinyl

Legality

On 2nd April 2010, the Advisory Council on the Misuse of Drugs

Advisory Council on the Misuse of Drugs

The Advisory Council on the Misuse of Drugs is a statutory and non-executive non-departmental British public body, which was established under the UK's Misuse of Drugs Act 1971.-Mandate:Its terms of reference, according to the Act, are as follows:...

in the UK

United Kingdom

The United Kingdom of Great Britain and Northern IrelandIn the United Kingdom and Dependencies, other languages have been officially recognised as legitimate autochthonous languages under the European Charter for Regional or Minority Languages...

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

Recreational drug use

Recreational drug use is the use of a drug, usually psychoactive, with the intention of creating or enhancing recreational experience. Such use is controversial, however, often being considered to be also drug abuse, and it is often illegal...

of mephedrone, a common member of the family. This ban covers compounds with the aforementioned general structure, with 28 compounds specifically named.
This text was added as an amendment to the Misuse of Drugs Act 1971

Misuse of Drugs Act 1971

The Misuse of Drugs Act 1971 is an Act of Parliament which represents UK action in line with treaty commitments under the Single Convention on Narcotic Drugs, the Convention on Psychotropic Substances, and the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic...

, to come into force on 16 April 2010. 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, along with a further broad based structure ban even more expansive than the last.
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.

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.

Chemical derivatives

Legality

See also