Synthetic cathinones are related to the parent compound cathinone.docx

7/25/2019 Synthetic cathinones are related to the parent compound cathinone.docx

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Synthetic cathinones are related to the parent compound cathinone (Figure 1), one of the

psychoactive principals in khat(Catha edulisForsk). Cathinone derivatives are the -keto (k)

analogues of a correspondingphenethylamine. he group includes several su!stances that have!een used as active pharmaceutical ingredients ("#$)of medicinal products, e.g. amfepramone

(diethylpropion% Figure &). Since the mid-&'''s, unregulated ring-su!stituted cathinonederivatives have appeared in the uropean recreational drugs market. he most commonly

availa!le cathinones sold on the recreational market in the period up to &'1' appear to !emephedrone (Figure ) and methylone (Figure *). hese products are usually encountered as

highly pure +hite or !ro+n po+ders. ing-su!stituted cathinone derivatives are claimed to have

effects similar to those of cocaine,amphetamineor "(ecstasy), !ut little is kno+n of theirdetailed pharmacology. "part from cathinone (Figure 1), methcathinone (Figure /) and t+o

"#$0s amfepramone (Figure &) and pyrovalerone, cathinone derivatives are not under

international control.

Chemistry

Figures 12 sho+ the naturally occurring cathinone (Figure 1) and si3 synthetic derivatives

(Figures &2).

Figure 1: Cathinone

olecular formula4 C561178olecular +eight4 1*5.15 g9mol

Figure 2: Amfepramone (diethylpropion)
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olecular formula4 C161578olecular +eight4 &'/.' g9mol

Figure 3: Mephedrone (4-methylmethcathinone 4-MMC)

olecular formula4 C1161/78olecular +eight4 122.&* g9mol

Figure 4: Methylone (!"-M#MA 34-methylenedio$y-%-methylcathinone)


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olecular formula4 C116178olecular +eight4 &'2.&& g9mol

Figure &: Methcathinone (ephedrone)

olecular formula4 C1'6178

olecular +eight4 1:.&& g9mol

Figure ': M# (34-methylenedio$ypyro*alerone)

olecular formula4 C1:6&178olecular +eight4 &2/./ g9mol

Figure +: Methedrone (!"-MMA 4-metho$ymethcathinone)


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olecular formula4 C1161/78&olecular +eight4 15.&* g9mol

Cathinone (Figure 1) and its derivatives are closely related to the phenethylamine family. hus

cathinone itself is -keto (k) amphetamine, &-aminopropiophenone or, more formally, &-amino-

1-phenyl-1-propanone ($;#"Csystematic name). he first synthetic cathinone that appeared inthe recreational drug market, methcathinone (Figure /), is k-methamphetamine, ephedrone or

N-methylcathinone. ost of the unregulated cathinone derivatives that have !een marketed in

the past fe+ years are ring-su!stituted, the most prevalent of +hich appears to !e mephedrone (*-

methylmethcathinone, *-C, Figure ). Some products sold are also likely to contain ami3ture of different chemicals. 8ther cathinones reported to the arly +arning system on ne+

drugsinclude methylone (k-"% ,*-methylenedio3y-7-methylcathinone, Figure *),

#< (,*-methylenedio3ypyrovalerone, Figure :), methedrone (k-#"% *-

metho3ymethcathinone, Figure 2) and ### (=-pyrrolidinopropiophenone).

>ike the phenethylamines, cathinone derivatives can e3ist in t+o stereoisomericforms, +hich

may differ in their potencies. he cathinone that occurs naturally in khatis the S-enantiomers.

6o+ever, it is likely that most ring-su!stituted derivatives are racemic mi3tures. $t is also!elieved that racemisation of all cathinone derivatives can occur through keto-enol tautomerism.

Cathinone is la!ile and transforms to a dimer(,:-dimethyl-&,/-diphenylpyra?ine). Cathinone

derivatives can also rearrange via a dihydropyra?ine dimer to form so-called @isocathinones0% "llkno+n cathinone derivatives are eitherN-alkylated or the nitrogen atom is part of apyrrolidine

ring, and most are produced as hydrochloridesalts. any illicit products areN-methylated, i.e.

ephedrone derivatives, +here!y mephedrone can !e descri!ed as *-methylephedrone. he

pyrrolidinederivatives (###, #


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0a/le 1

he structural classification of cathinone derivatives found in drug sei?ures, collected samples oroffered for sale on $nternet sites (see Figure A). hose that are or have !een used as active

pharmaceutical ingredients ("#$) are sho+n em!oldened.

1 2 3 4 & %ame

6 6 6 6 6 Cathinone

ethyl 6 6 6 6 ethcathinone (ephedrone)

ethyl ethyl 6 6 6 N,N-imethylcathinone (metamfepramone)

thyl 6 6 6 6 N-thylcathinone (C)

ethyl 6 6 ethyl 6 Buphedronethyl 6 *-ethyl 6 6 *-ethyl-N-ethylcathinone

ethyl 6 *-ethyl 6 6 ephedrone (*-C% -C")

thyl thyl 6 6 6 Amfepramone

t-Butyl 6 -C$ 6 6 upropion

ethyl 6,*-ethylenedio3y

6 6 ethylone (k-")

thyl 6,*-

ethylenedio3y6 6 thylone (k-")

ethyl 6 *-ethyl ethyl 6 Butylone (k-BB)

ethyl 6 *-etho3y 6 6 ethedrone (k-#")ethyl 6 *-F 6 6 Flephedrone (*-FC)

ethyl 6 -F 6 6 -Fluoromethcathinone (-FC)

pyrrolidinoD 6 6 6 =-#yrrolidinopropiophenone (###)

pyrrolidinoD *-ethyl 6 6*-ethyl-=-pyrrolidinopropiophenone(###)


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1 2 3 4 & %ame

pyrrolidinoD *-e8 6 6*-metho3y-=-pyrrolidinopropiophenone

(8###)

pyrrolidinoD *-ethyl #ropyl 6*-ethyl-=-pyrrolidino-he3anophenone

(#6#)

pyrrolidinoD *-ethyl thyl 6 yro*alerone

pyrrolidinoD *-ethyl ethyl 6*-ethyl-=-pyrrolidino-!utyrophenone

(#B#)

pyrrolidinoD *-ethyl 6 ethyl*-ethyl-=-pyrrolidino-=-

methylpropiophenone

pyrrolidinoD,*-

ethylenedio3y6 6

,*-ethylenedio3y-=-

pyrrolidinopropiophenone (###)

pyrrolidinoD,*-

ethylenedio3ythyl 6 ,*-ethylenedio3ypyrovalerone (#ike cocaine, the resulting @high0 of mephedrone is short-lived.

ConseEuently, users may consume several doses in succession, up to 1 g in a session. his is
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supported !y the finding that the most common @+rap si?e0 of mephedrone found in police

sei?ures in the ;nited ingdom is close to 2/' mg.

hepyrrolidine ringand the tertiary aminogroup in #< could lead to a more lipophilic, i.e.morepotent, molecule% $nternet user-forums suggest that the dose is as lo+ as /1' mg.

Furthermore, it should !e noted that p-metho3yphenethylamines (e.g. #", #") are kno+nto have a particularly high to3icity, and this property might translate to their k-analogues. For

e3ample, methedrone (p-metho3ymethcathinone) has !een detected in a fe+ fatalities.

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ynthesis and precursors

Simple derivatives such as methcathinone andN,N-dimethylcathinone can !e synthesised !y

o3idation of ephedrine (or pseudoephedrine) andN-methylephedrine (orN-methylpseudoephedrine) respectively. his reEuires reacting the precursor +ith a solution of

potassium permanganate in dilute sulfuric acid. he precursors can !e o!tained as specificenantiomers, there!y ensuring that the synthesis is stereoselective. Cathinone itself can !e madein a similar +ay, starting from phenylpropanolamine (norephedrine). 8ne of the ha?ards of the

permanganate process is that users can suffer manganese poisoning if the product is not purified.

he ring-su!stitutedN-methylcathinone derivatives are !est synthesised !y reacting the suita!ly

su!stituted !romopropiophenone +ith methylamine% the result is al+ays racemic.$n the case ofmethylone, for e3ample, &-!romo-,*-methylenedio3y-propiophenone can !e prepared !y

reacting ,*-methylenedio3ypropiophenone +ith !romine. hese precursor su!stances are

readily availa!le and none of them is under international control. 8ther methods are reEuired toproduce thepyrrolidinederivatives, !ut apart from #


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+ith the phenethylamines, acronyms are common. hus #< stands for ,*-

methylenedio3ypyrovalerone, *-FC for *-fluoromethcathinone (flephedrone), and *-C for

*-methylmethcathinone (mephedrone). ;ser names for mephedrone include -Cat, meph, drone,miao+, meo+ meo+, su!coca-1 and !u!!les% +hile methylone is sometimes kno+n as op Cat.

6o+ever, these su!stances are often sold in products that have a large num!er of !rand names

that change rapidly over time and +here the specific content is often not given. he chemicalnames can lead to confusion% methylone, mephedrone and methedrone should !e distinguished

from each other and from the unrelated narcotic analgesic methadone. "lthough k-BB is

often descri!ed as @!utylone0, !utylone has also !een used as a proprietary name for theunrelated!ar!ituratepento!ar!ital.

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Analysis

Cathinone derivatives do not give a coloured reaction +ith the arEuis field test. "nalysis using

GCSand $nfrared ($) spectroscopyis straightfor+ard. "lthough pure reference samples ofsome derivatives may not !e commercially availa!le, analytical profiles for most have !een

pu!lished. $mmunoassayfield tests formethamphetaminegive false positive reactions +ith some

cathinone derivatives.

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0ypical purities

Some po+ders containing mephedrone and related compounds have !een adulterated +ith other

drugs such as ketamine, cocaine, paracetamol or pipera?ine derivatives, !ut most appear to !ehighly pure as Hudged !y $ spectroscopy.

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Control status

Cathinone and methcathinone are listed in Schedule $ of the ;nited 7ations 1521 Convention on

#sychotropic Su!stances. "mfepramone and pyrovalerone are in Schedule $< of thatConvention, !ut other derivatives are not under international control. " fe+ cathinone derivatives

are controlled in some em!er States under drug control or eEuivalent legislation, for e3ample4

mephedrone (Belgium, enmark, Germany, stonia, $reland, France, $taly, >ithuania, omania,S+eden, Croatia and 7or+ay)% methylone (enmark, $reland, omania and S+eden)% !utylone

(enmark, $reland, omania, S+eden and 7or+ay)% #< (enmark, $reland, Finland and

S+eden)% and flephedrone (enmark, $reland and omania). Generic control in the ;nited

ingdom covers a +ide group of cathinone derivatives. ephedrone is controlled undermedicines legislation in Finland and the 7etherlands and Finland.
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By Council ecision of & ecem!er &'1', *-methylmethcathinone (mephedrone) +as su!mitted

to control measures in ; em!er States (&'1'92/59;).

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re*alence

Synthetic cathinones have only recently appeared on the recreational drugs market, and fe+

formal epidemiological studies have !een pu!lished. here are no nation+ide studies +ithin the

; on the prevalence of mephedrone use in any given population. $n an online survey conductedin late &'1' in colla!oration +ith the ;nited ingdom0s dance music maga?ine i3mag,

mephedrone +as the fourth most-commonly used drug in the past year (aftercanna!is,ecstasy

and cocaine) and had !een tried !y :1 I of respondents. &/ I of respondents had tried it +ithinthe last month, +hich +as a decrease compared to .:I in late &''5. $t should !e noted that

mephedrone +as scheduled in the ; mid-april &'1'.

"lthough not controlled in many countries, synthetic cathinones are regularly su!mitted toforensic la!oratories !y police and customs for identification. he num!er of such su!missionsincreased rapidly during the second half of &''5. ethylone +as one of the first ring-su!stituted

synthetic cathinones to !e reported in the ; (7etherlands, S+eden, &''/), !ut mephedrone has

!ecome the most commonly seen derivative. $nformation on sei?ures and samples from the

7etherlands indicate that ta!lets sold as ecstasy, !ut actually containing mephedrone (sometimesin com!ination +ith "), appeared on the market for the first time in &''5. 6o+ever, the

a!sence of systematic data makes it difficult to comment +ith confidence on the availa!ility of

different cathinone products, although reports do suggest that availa!ility varies over time andplace.

;p until the introduction of control measures in the ; in "pril &'1', mephedrone and othersynthetic cathinones +ere readily availa!le either from $nternet suppliers or retail outlets. "n

C" snapshot of the availa!ility of mephedrone on the $nternet in arch &'1' sho+ed thatat least 22 +e!sites, +ould sell and ship the su!stance to a user in the ;. $n July &'11, 1A

+e!sites +ere identified claiming to sell mephedrone.

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treet price

ephedrone and related compounds are primarily sold on +e!sites or in @head shops0. he &'1'C" snapshot sho+ed prices ranging !et+een ; 1' and 1/ for one gram, +ith

discounts offered for !igger Euantities. $n the &'11 C" snapshot prices +ere ranging

!et+een ; 1A and &/ for one gram.

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Medical use
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"mfepramone and pyrovalerone have !een used as anorectics, !ut are no+ largely o!solete.

Bupropion has antidepressant properties and is used as an aid for those +ho +ish to Euit to!acco

smoking.

katinona sintetis terkait dengan senyawa induk cathinone (Gambar 1), salah satu

pelaku psikoaktif di khat (Catha edulis Forsk). derivatif cathinone adalah !keto (k)analog dari phenethylamine yang sesuai. "elompok ini mencakup beberapa #at

yang telah digunakan sebagai bahan aktif farmasi ($%&) dari produk obat, misalnya

amfepramone (diethylpropion' Gambar ). e*ak pertengahan +++!an, tidak diatur

cincin tersubstitusi turunan cathinone telah muncul di pasar narkoba ropa. -he

katinona yang paling umum tersedia di*ual di pasar rekreasi pada periode hingga

+1+ tampak mephedrone (Gambar ) dan metilon (Gambar /). %roduk!produk ini

biasanya ditemui sebagai bubuk putih atau coklat yang sangat murni. derivatif

cathinone cincin tersubstitusi yang diklaim memiliki efek mirip dengan kokain,

amfetamin atau 00$ (ekstasi), tetapi sedikit yang diketahui farmakologi rinci.

-erlepas dari cathinone (Gambar 1), methcathinone (Gambar 2) dan dua $%&

amfepramone (Gambar ) dan pyrovalerone, turunan cathinone tidak berada di

bawah pengawasan internasional.

Cathinone (Gambar 1) dan turunannya terkait erat dengan keluarga

phenethylamine. 3adi cathinone itu sendiri adalah !keto (k) amfetamin, !

aminopropiophenone atau, lebih formal, !amino!1!fenil!1!propanon (&4%$C nama

sistematis). -he cathinone sintetis pertama yang muncul di pasar narkoba,

methcathinone (Gambar 2), adalah k!methamphetamine, ephedrone atau 5!

methylcathinone. ebagian besar turunan cathinone tidak diatur yang telah

dipasarkan di beberapa tahun terakhir adalah cincin tersubstitusi, yang paling

umum yang tampaknya men*adi mephedrone (/!methylmethcathinone, /!00C,Gambar ). 6eberapa produk yang di*ual *uga mungkin mengandung campuran

bahan kimia yang berbeda. katinona lainnya dilaporkan ke sistem peringatan dini

pada obat baru termasuk metilon (k!00$' ,/!methylenedio7y!5!

methylcathinone, Gambar /), 0%8 (,/!methylenedio7ypyrovalerone, Gambar 9),

methedrone (k!%00$' /!metho7ymethcathinone, Gambar :) dan %%% (;!

pyrrolidinopropiophenone).

eperti phenethylamines, turunan cathinone bisa eksis dalam dua bentuk

stereoisomer, yang mungkin berbeda dalam potensi mereka. -he cathinone yang

ter*adi secara alami dalam khat adalah !enantiomer. 5amun, ada kemungkinan

bahwa sebagian besar turunan cincin diganti adalah campuran rasemat.


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dimana mephedrone dapat digambarkan sebagai /!methylephedrone. -he

pyrrolidine derivatif (%%%, 0%8) dapat dianggap sebagai sub!set =obat desainer=

berbagi kerangka yang sama seperti pyrovalerone. -abel 1 daftar turunan cathinone

yang telah digunakan sebagai $%&, ditemukan dalam ke*ang obat, sampel yang

dikumpulkan untuk tu*uan monitoring atau ditawarkan untuk di*ual di situs &nternet

(lihat Gambar >). 5aphyrone (1!naphthalen!!yl!!pyrrolidin!1!ylpentan!1!satu),sebuah cathinone derivatif yang lebih kompleks, tidak termasuk dalam -abel 1.

Liquid Chromatograpy Mass Spectroscopyadalah dua alat yang diga!ungkan menHadi

satu, yang !erfungsi untuk memisahkan !e!erapa senya+a atau campuran senya+a !erdasarkan

kepolarannya (prinsip kerHa kromatografi), dimana setelah campuran senya+a terse!ut terpisah,

maka senya+a yang murni akan diidentifikasi !erat molekulnya. ata yang didapatkan adalah

!erat molekul ditam!ah !e!erapa muatan dan !erat molekul pelarut."dapun cara kerHa liquid chromatograpy adalah sama dengan 6#>C atau liquid

chromatograpylain, adalah 4

a. "nalit !ersama dengan eluen darisyringe pumpatau >C masuk ke dalam cappilary. i dalam

cappilaryterdapat anoda (kutup negatif) pada taylor conedan katoda (kutup negatif) di dekat

masukan analit dan eluen. utup ini !erfungsi agar muatan yang !erkumpul pada taylor cone

adalah muatan positif sehingga nantinya saat terHadi penyemprotan dan ter!entuk droplet (tetes

tetes) tidak !erga!ung ga!ung menHadi droplet yang le!ih !esar lagi.

!. "nalit dan solven(eluen) disemprotkan melalui taylor cone.

"kan ter!entuk droplet droplet dimana droplet droplet itu akan mengalami tahap evaporasi

solven untuk mengurangi solven yang menempel di analit. arena suatu saat, apa!ila terHadi

evaporasi secara terus menerus maka solven yang meliputi analit terkungkung dalam muatan

positif yang !erle!ih, dalam !ahasa $nggris tahap seperti ini dise!ut the rayleigh limit is

reached, maka akan terHadi e3plosion yang dise!ut coulombic explosion dimana akan terHadi

pemecahan droplet (tetesan) tadi. "da !e!erapa kemungkinan yang terHadi pada droplet droplet

terse!ut, yaitu 4


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1) analit akan tertam!ahi satu muatan positif

&) analit akan tertam!ahi !e!erapa muatan positif

) analit akan tertam!ahi satu muatan positif dan satu molekul solven*) analit akan tertam!ahi satu muatan positif dan !e!erapa molekul solven

/) analit akant tertam!ahi !e!erapa muatan positif dan !e!erapa molekul solven.

c. roplet yang mengalami coulombic exsploisonterse!ut akan masuk ke dalam conedimana di

sisi kiri dan kanannya sudah mengalir gas 7itrogen (7&). Gas ini !erfungsi agar analit yang

terHadi tadi sta!il dalam !entuknya dan tidak terganggu oleh pengaruh gas oksigen. roplet

masuk ke dalam cappilarytransfer lalu akan dianalisis melalui mass spectrometer.

uatan positif pada solven !erasal dari ion-ion 7a K, >iK, K, 76*K, dan kation lain. 8leh

karena pada daerah taylorcone dalam capillary nedle !ermuatan negatif,maka analit dalam

solven yang memiliki muatan positif akan !erkumpul didaerah taylorcone. "ki!atnya pada saat

penyemprotan tetesan-tetesan (droplet) permukaanya memiliki muatan positif, dan masing-

masing tetesan (droplet) tidak saling menempel lagi (mem!entuk tetesan yang le!ih !esar). #ada

spektra sering terHadi penam!ahan !erat molekul ion-ion terse!ut disamping penam!ahan !erat

molekul atau !iasanya ditulis dengan L K molekul ion-ionM. emungkinan ion molekul yang

terdeteksi di mass spectroscopyadalah L K 6KM, L - 6KM, serta analit dengan tam!ahan seperti

7aK, K, 68K, 76*

K, dan molekul dari fase gerak ( >C-S !ook, "udrey, &'').

Documents

Synthetic cathinones are related to the parent compound cathinone.docx