MEPH and MDPV Synthetic Cathinones: “Non-addictive,” Schedule I

Substances

Alexandra Traynor

FYS100HC: the Science of Addiction

Dr. Hagan

19 November, 2014

Abstract

Synthetic cathinones are not classified in the Diagnostic and Statistical Manual of

Mental Disorders, Fifth Edition, as addictive substances. However, the United States

government assigned synthetic cathinones as Schedule I compounds in 2012, due to the

imminent health hazard they began exerting on the country.

The most psychoactive of the synthetic cathinone central nervous system

stimulants are mephedrone (MEPH) and 3,4-methylenedioxypyrovalerone (MDPV).

Coincidentally, they also happen to be the most widely used. MEPH and MDPV are

typically compounds that make up a bath salt. When consumed simultaneously, MEPH

and MDPV can be deadly for the body. One conducted study calculated a result that

showed MDPV to be 9x as potent on the body as cocaine.

Synthetic cathinones, analogues of the naturally occurring compound cathinone,

share many similar properties with amphetamines. Many chemical and pharmacological

properties are shared between amphetamines and synthetic cathinones. Due to these

similarities, many analysts deduce synthetic cathinones to have a high potential for

addiction.

Although MEPH and MDPV are not classified as addictive substances, they have

a high potential to be. Their pharmacological properties, ways in which they enter the

body, and most importantly their pharmacological properties, all point to the deduction

that synthetic cathinones, particularly MEPH and MDPV, are addictive.

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Introduction

Bath Salts are a recently new craze of drug stimulants. These amphetamine-like

substances (Mas-Morey, Visser, Winkelmolen, & Touw, 2013, p. 353) gained a spotlight

in 2011 after a New York Times article published crazed human acts caused by bath salt

usage (Goodnough, 2011). It reported a man in Pennsylvania who entered a monastery

and stabbed a priest, and a woman who scratched her body terribly because she thought

there was something under her skin; the emergency room doctor reported her looking “…

like she had been dragged through a briar bush for several miles” (Goodnough, 2011).

Episodes similar to the ones previously stated exemplify the type of behavior linked with

bath salts: psychoactive and hallucinogenic (Baumann et. al, 2012, p. 552; Penders &

Gestring, 2011, p. 523).

Bath salts are a synthetic breed of drugs. They are a mixture of numerous

substances mainly consisting of psychoactive molecular compounds known as synthetic

cathinones (Cameron et al, 2013, p.1754). Synthetic cathinone substances are analogues

of the naturally occurring molecular component cathinone (Lopez et al, 2013, p. 64). The

molecule cathinone is the primary psychoactive component of the khat (Catha edulis)

plant, which is native to East Africa and the Arabian Peninsula. Cathinone proffers

amphetamine-like effects of euphoria, energy, hyperactivity, and increased alertness

(National Institute, 2013, p. 1). In 1993 the Drug Enforcement Administration (DEA)

placed cathinone on the Controlled Substance Act list under Schedule I because it posed

an imminent threat to public safety (Lee, 1995, p 116); MDPV was reported as the fifth

most commonly used hallucinogen in the United States (German et al., 2014, p. 4). In

order to mimic the effects of cathinone but sidestep the legal system, drug dealers

designed synthetic cathinones. Today these substances are dubbed “designer drugs” and

normally called by their street name, bath salts (Cameron, 2013, p. 1750).

The bath salt craze jumpstarted in 2009 and continued through 2010, when the

drug reached a level of representation that threatened the health of the United States

(German, Fleckenstein, & Hanson, 2014, p. 2). Because of their rising popularity,

President Obama signed the Synthetic Drug Abuse Prevention Act of 2012 which

classified two synthetic cathinones as Substance I controlled drugs. The Act made the

purchase, distribution, provision, and possession of mephedrone (MEPH) and 3,4-

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methylenedioxypyrovalerone (MDPV) illegal (Miller and Stogner 2014). Since this

declaration, the manufacturing and distribution of diverse synthetic cathinones, called

“designer drugs”, became common occurrences (p. 7).

Designer drugs are “legal” because their molecular structure is different enough

from the scheduled synthetic cathinones to avoid scheduling by the DEA (Banks, Works,

Rusyniak, & Sprague, 2014, p. 633). However, the synthetic cathinone’s structure needs

to share specific qualities with cathinone in order to elicit a comparable response (p. 634).

These minor changes in molecular formula of synthetic cathinones create a huge

problem for law enforcement agencies. The authorities have a difficult time staying

abreast of the synthetic cathinone evolution, because as soon as one form of a synthetic

cathinone is pronounced illegal, another molecular form is designed (Mas-Morey et. al,

2013, p. 353). There are thirty known derivatives of synthetic cathinones (Cameron et. al,

2013, p. 1754). The designer drug bath salts circumvent detection by selling as common

household cleaners or plant food. With labels that read “not for human consumption”

bath salts navigate around the legal system (den Hollander, Rozov, Linden, Uusi-Oukari,

Ojanperä, & Korpi, 2013, p. 502).

Bath Salt Addiction

The Diagnostic and Statistical Manual of Mental Disorders, Fifth Edition (DSM

V), does not explicitly state synthetic cathinones, components of bath salts, as addictive.

It does classify amphetamines as an addiction because of the psychoactive symptoms

amphetamines elicit from the body – including but not limited to hallucinations,

hyperthermia, tachycardia, and psychoactive behaviors (Lewin, Seltzman, Carroll,

Mascarella, & Reddy, 2014, p. 16; Banks et al., 2014, p. 634; German et al., 2014, p. 3) –

as well as tolerance built from repetitive use. Amphetamines and synthetic cathinones fall

under the same class of chemical compounds called phenethylamines because they share

many pharmacological and chemical properties, including a pharmacophore core of

phenyl (Banks et al., 2014, p. 633). Phenethylamines are known for their psychoactive

effects on the central nervous system (CNS) caused by increased amounts of monoamines

in the synaptic cleft (Mas-Morey et al., 2013, p. 354; Cameron et al., 2013, p. 1750).

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The pharmacological properties of the phenethylamine chemical class share

similar functions exhibited by like effects on behavior and mental function (Cameron et

al., 2012, p. 1).

Synthetic cathinones ultimately induce molecular and physiological responses

similar to those in amphetamine addictions; therefore, analysts deduce that bath salts

have the potential to be addictive.

Consumption

Bath salts are administered to the body in a multitude of ways. Most commonly

they are snorted through the nasal passages, taken orally, injected intravenously by

needle, or smoked (Mas-Morey et al., 2013, p. 353; Waitz, 2011, p. 396). Intravenous

routes and the inhalation of bath salts cause the most harm to the body (Waitz, 2011, p.

396). Such entry creates the quickest route of admittance, the fastest passage to and

through the blood brain barrier, and ultimately the greatest high. Other entryways include

administration by parenteral injection, absorption through the rectus, and insertion into

the gums (Mas-Morey et al., 2013, p. 355). Consumption patterns commonly consist of

binge usage in social settings, typically combined with other drugs (German et al., 2014,

p. 4). Synthetic cathinones have a high potential for abuse because of their consumption

patterns (p. 7).

Phenethylamine Analogues

Amphetamine, cathinone, and synthetic cathinones are analogues because they

share the same phenethylamine pharmacophore: a phenyl group attached to a linear chain

Phenethylamine Amphetamine

Figure 1

3,4-methylenedioxypyrovalerone(MDPV)

Mephedrone(MEPH)

Cathinone

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of two carbon atoms ending in an amine group, as seen in Figure 1 (Banks et al., 2014, p.

634; European Monitoring Centre for Drugs and Drug Addiction, 2012; PubChem, 2014,

2D Structure). Figure 1 shows the similarity in structure between amphetamine and

multiple synthetic cathinones (V). Similar pharmacophore in molecular compounds is

essential for the compounds to exert the same effect.

The phenethylamine molecule in Figure 1 terminates in a cytosine amine group.

Amphetamine terminates in a cytosine and methyl group. Cathinone exhibits the same

structure as amphetamine, with the addition of a carbonyl group (=O) at the β-carbon

(Banks et al., 2014, p. 633). Synthetic cathinones MEPH and MDPV have a modified

structure of cathinone: MEPH has a methyl group attached to its phenyl ring, a cytosine

group attached to the fourth carbon of the phenyl group, and a carbonyl group attached at

the α-carbon. MDPV has a pyrrodiniyl ring and propane molecule added to its α-carbon

and a methylenedioxy ring attached to the aromatic ring of the β-ketone backbone

(German et al., 2014, p. 4). These minute changes are responsible for notable differences

in the molecules’ functions, but still link amphetamines and synthetic cathinones closely

to each other (Banks et al., 2014, p. 633).

The more carbon atoms attached to a molecule’s phenyl group, the greater the

length of carbon’s bond to the α-carbon, and the addition of highly electronegative atoms,

such as fluorine or oxygen, determines how great the lipophilic nature of a molecule will

be. A molecule’s absorption rate into the body is dependent on its lipophilic nature.

MEPH and MDPV are largely lipophilic; this means they are easily absorbed by the body

and impose a greater reaction than amphetamine on the release and uptake of monoamine

molecules (Banks et al., 2014, p. 633).

As seen in Figure 1, synthetic cathinones MDPV and MEPH structures contain

longer carbon chains bonded to the α-carbon than amphetamine, and are composed of a

greater number of carbon atoms than amphetamine. These characteristics provide bath

salts composed of MDPV and MEPH a greater absorption rate into the body than

amphetamine, due to MDPV’s and MEPH’s greater lipophilicity (German et al., 2014, p.

4).

The varying molecular groups added onto the compounds shown in Figure 1 have

an impact on the compound’s affinity for monoamine transporters dopamine, serotonin,

6

and norepinephrine. The addition of β-ketone on MDPV, for example, increases MDPV’s

selectivity for the dopamine transporter over the serotonin transporter by 120-fold (Banks

et al., 2014, p. 634). This information provides a reason for crazed behaviors exhibited by

a bath salt user.

The similarity of a pharmacophore phenyl group amongst amphetamine,

cathinone, and synthetic cathinones MEPH and MDPV provides each molecular

phenethylamine with the same basic function of neurotransmission in the CNS (Bonano

et al., 2014, p. 200). That common chemical structural base provides a connection

between amphetamine and synthetic cathinones, increasing the synthetic cathinones’

potential for addiction (Banks et al., 2014, p. 634).

A study performed by researchers Cameron et al. (2012) exemplified the

increased activity of MEPH and MDPV when compared to certain amphetamine

substances (p. 1750). This study will be discussed in the following section.

Dopamine Pathway

Synthetic cathinones and amphetamines interact with the same catecholamine,

monoamine neurotransmitter receptors – dopamine, serotonin, and norepinephrine (p.

1755). The main receptor synthetic cathinones MDPV and MEPH, as well as

amphetamines, interact with on the neuron is the dopamine receptor. Dopamine is an

endogenous monoamine molecule whose levels in the brain can be manipulated by

exogenous synthetic cathinones (Banks et al., 2014, p. 638).

The dopamine pathway in the brain begins when an exogenous substance, a drug,

travels through the blood stream up to the blood brain barrier (BBB). The drug reaches

the BBB, enters the brain, and joins the mesolimbic pathway (Williams College, 1998, p.

Figure 1 illustrates the dopaminergic pathway in the human brain, commencing at the blood brain barrier.

Figure 2

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22). Figure 2 presents the pathway dopamine takes to enter and traverse the brain

(Dopamine Synthesis, 2002).

Dopamine is mainly stored in the presynaptic terminal in the brain’s nucleus

accumbens. Figure 3 shows the location of the nucleus accumbens in the brain

(Dopamine Pathways, n.d.). The dopamine neurotransmitter leaves the presynaptic

neuron vesicle once an action potential prompts its release into the postsynaptic cleft

between the presynaptic neuron and postsynaptic neuron (for clarification see Figure 2)

(Williams College, 1998, p. 22). Receptors embedded on the postsynaptic neuron’s

plasma membrane detect and interact with the dopamine neurotransmitter. The dopamine

neurotransmitter then binds to a dopamine receptor on the postsynaptic neuron’s plasma

membrane and activates the G-protein coupled metabotropic receptor (p. 23). Its binding

with the G-protein receptor causes a conformational change of the ion channel on the

postsynaptic neuron, allowing sodium (Na+) ions into the cell, and creating an action

potential (p. 23). When a bath salt composed of MDPV and MEPH enters the body, it

alters the aforementioned dopaminergic pathway. MEPH binds to the dopamine

transporters embedded in the plasma membrane of the presynaptic neuron and increases

the amount of dopamine neurotransmitters released into the postsynaptic cleft. MDPV

inhibits the reuptake of dopamine on the postsynaptic neuron (Cameron et al., 2013, p.

Figure 3 identifies main sections of the brain. Dopamine is heavily concentrated in the nucleus accumbens, located above the VTA.

Figure 3

8

1755). Figure 4 describes a normal synaptic transmission alongside a synaptic

transmission after bath salt use (Banks et al., 2014, p. 638 modified). The diagram in

Figure 4 demonstrates the existence of dopamine levels in the postsynaptic in much

greater amounts after bath salt use as compared to without bath salt use. In synaptic

transmission after bath salt use, the MEPH molecule excites the presynaptic neuron so

that it to releases greater levels of dopamine into the postsynaptic cleft than a normal

synaptic transmission (Banks et al., 2014, p. 638). Oppositely, MDPV interacts with the

dopamine transporter on the presynaptic neuron to inhibit the reuptake of dopamine (p.

638 modified). This creates excess amounts of dopamine, which hang around in the

synapse located between the presynaptic neuron and postsynaptic neuron. The previously

mentioned study conducted by Cameron et. al (2012) compared dopamine levels present

in the postsynaptic cleft after the application of different exogenous substances to oocyte

cells (Cameron et al., 2013, p. 1750).

Comparison of Amphetamines and Synthetic Cathinones

Previous studies have shown that synthetic cathinones, particularly MDPV and

MEPH, yield a greater impact on monoamine, catecholamine-selective, neurotransmitter

9

release in the brain as compared to amphetamine compounds, namely cocaine and

methamphetamine (p. 1753). Cameron et. al (2012) aimed to discern the difference in

dopamine levels produced by bath salts and dopamine levels produced by amphetamines.

Cameron et. al (2012) observed dopamine levels released by oocytes, a cell from a female

ovary, after the application of synthetic cathinones and amphetamines. The dopamine

levels were measured at the dopamine transporters of a presynaptic and postsynaptic

neuron in the oocyte. The exogenous substances observed were the most prevalent

synthetic cathinone bath salt components - MDPV, MEPH, and a mixture of MDPV and

MEPH. The amphetamine compounds observed were cocaine and methamphetamine (p.

1751).

A two-electrode voltage clamp was placed on each of the oocytes to gain data of

dopamine levels released at the dopamine transporter protein on the presynaptic neuron

as well as the postsynaptic neuron. Inward, inhibitory currents of applied solutions were

measured alongside outward, hyperpolarizing currents at the dopamine transporter.

Oocytes were attached to a voltage clamp that produced and kept a running electric

current of -60 mV, close to cells’ resting potential. The -60 mV electric current would be

compared against the dopamine induced currents in each 10 µM oocyte (p.1752). Data of

dopamine levels was recorded using

Clampfit 10.2 software and a filtering

of 1-kHz. The drug solution was

applied to the oocyte at 10 µM for 60s.

The current of each solution was

measured with the assistance of drug-

induced I(V) curves (Figure 5). The

drug-induced I(V) curve was

calculated by subtracting the curve of

solution without the drug substance

from the curve of the solution with the

drug containing substance. This

calculation is visualized in Figure 5 (p.

1754,).

Table of abbreviationsCOC= cocaineDA=dopamineMDPV=3,4-methylenedioxypyro-valeroneMEPH=mephedrone

Figure 5 displays the calculated drug-induced I(V) curves of an experiment comparing synthetic cathinones and amphetamines. MDPV produced a greater inhibitory current than COC whereas MEPH produced a lesser excitatory current than DA.

Figure 5

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Results of Synthetic Cathinones vs. Amphetamines

The I(V) curves of cocaine (COC) and dopamine (DA) are control groups because

their signal currents of dopamine transporters are known. Cocaine is a molecule

recognized for its production of an inhibitory, hyperpolarizing current during dopamine

interactions (p. 1750). As seen in Figure 5, MDPV produced an inhibitory curve similar

to cocaine, suggesting MDPV is also an uptake inhibitor of presynaptic dopamine

neuroreceptors (p. 1751). This result supports data collected in other studies that similarly

identify MDPV as a selective transporter reuptake blocker (Baumann et al., 2012, p. 553).

MDPV not only blocked a greater portion of the endogenous dopamine leak than

cocaine, but it also lasted for 30 minutes longer than cocaine. MDPV was measured to

have an affect on assays that is 20x more potent more potent than cocaine (Cameron et

al., 2013, p. 1753).

Contrary to MDPV, which sends an inhibitory signal to the dopamine transporters

on a presynaptic neuron, Cameron et al.’s (2012) study showed MEPH sending an

excitatory, depolarizing current to the dopamine transporters embedded in presynaptic

neurons. The depolarizing signal sent to the dopamine transporters in the presynaptic

neuron resulted in the release of large amounts of dopamine into the postsynaptic cleft.

Figure 5 allows a comparison to be drawn between the excitatory current caused by

MEPH and the excitatory current caused by dopamine transporters on the presynaptic

neuron. When the current of MEPH at the oocyte’s dopamine transporter was measured,

it revealed a blocking uptake of dopamine half as potent as dopamine itself.

The calculated I(V) curve of MEPH displayed a lower excitatory current of

dopamine transporters on the presynaptic dopamine transporters.

The Cameron et. al (2012) experiment demonstrated the differing effects of

MDPV, MEPH, MDPV + MEPH, cocaine, and methamphetamine. Cameron et. al (2013)

externally applied cocaine, methamphetamine, MDPV, and MEPH to oocyte cells, an

ovary cell, and measured the rate at which dopamine was produced at the dopamine

transporter protein (p. 1752). MDPV inhibited the uptake of dopamine transmitters more

potently than cocaine; MDPV’s measured inhibitory current of 28 nM was 35x more

potent than cocaine’s measured current of 995 nM. MDPV also exhibited a lengthened its

effect on the oocyte’s transmitter- up to thirty minutes after removal, the dopamine

11

transporters on the postsynaptic oocyte neuron still exerted a hyperpolarizing effect (p.

1753).

The overall result of this study showed that MEPH and MDPV produce opposite

effects at dopamine transporters. MEPH depolarizes the dopamine transporter of the

postsynaptic neuron whereas MDPV hyperpolarizes the dopamine receptor on the

presynaptic neuron (p. 1750). MEPH releases excess amounts of dopamine from the

presynaptic neuron, and MDPV inhibits the reuptake of that excess dopamine at the

dopamine transporter of the presynaptic neuron. By preventing reuptake, dopamine levels

in the synaptic cleft are increased (refer to Figure 4), causing the physical effects seen

after bath salt usage. When manufactured in the same compound, MDPV and MEPH

work together to exert a greater potency on the dopamine neurons, and the body, than

cocaine or methamphetamine (p. 1755).

These opposite reactions exhibited by MEPH and MDPV create a synergistic

combination that could account for the adverse physiological effects brought on by bath

salt abuse. When a synthetic cathinone composed of MEPH and MDPV is applied to the

human body, MEPH first targets the dopamine transporters on the presynaptic neuron.

Not long after, MDPV inhibits the reuptake of dopamine at the postsynaptic neuron.

These simultaneous actions pose a dangerous situation for the bath salt user. The

combination of depolarization signals followed by hyperpolarization signals creates a

stimulation of the CNS greater than either of the compounds’ effects when administered

singly (p. 1756).

Conclusion

Bath salts pose an imminent threat to society because of the psychoactive

symptoms they induce on their users. Synthetic cathinones, the psychoactive stimulant

component of bath salts, are not classified as an addiction, but they have great

qualifications.

Bath salt components, in particular mephedrone and 3,4-

methylenedioxypyrovalerone, are classified as synthetic cathinones. Synthetic cathinones

share very similar pharmacological properties with the central nervous system stimulant

amphetamine. MEPH and MDPV share their pharmacophore with amphetamine, which

provides MEPH, MDPV, and amphetamines with the same function. The phenethylamine

12

pharmacophore is the entity that enables synthetic cathinones and amphetamines to elicit

similar psychoactive and hallucinogenic symptoms.

The similar structure of amphetamines and synthetic cathinones allows the

compounds to interact with the same catecholamine, monoamine receptors of dopamine,

serotonin, and norepinephrine. Amphetamines and synthetic cathinones both utilize the

dopamine neurotransmitters, which are located in the plasma membrane of presynaptic

and postsynaptic neurons. Most of the dopaminergic activity performed by synthetic

cathinones happens in the nucleus accumbens of the mesolimbic pathway.

Although the DSM V does not classify synthetic cathinones MDPV and MEPH as

addictive substances, MDPV and MEPH provoke a more potent reaction at dopamine

neurotransmitter sites than amphetamines. The experiment performed by Cameron et al.

(2013) exemplified the opposing effects produce when MDPV and MEPH are consumed

simultaneously. When taken together, the depolarization of presynaptic dopamine

transporters by MEPH increases the dopamine level in the synaptic cleft. Those

dopamine levels then remain in the synaptic cleft because MDPV inhibits their reuptake

on the presynaptic dopamine neuron with a hyperpolarizing signal. Symptoms from bath

salt usage like hallucinations, hyperthermia, and agitation are the result of increased

dopamine levels in the synapse. The combination of MDPV and MEPH applied to the

body at the same time induces dangerous results, especially because the pharmacological

properties of MDPV and MEPH have not been fully discovered.

The study by Cameron et al. (2013) also resulted in MDPV outinhibiting the

amphetamine cocaine-MDPV stimulates a potency on the body 9x greater than cocaine.

The symptoms of MDPV and MEPH, their pharmacological properties, their shared

phenethylamine pharmacophore with amphetamines, and their increased dopaminergic

activity in the brain are all examples of connections to amphetamines. The

aforementioned properties of MEPH and MDPV exemplify their similarity with

amphetamines. Because amphetamines are highly addictive, the potential for bath salts

composed of MDPV and MEPH to be severely addictive is highly plausible.

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