Methedrone

Last updated
Methedrone
4-Methoxymethcathinone.svg
Clinical data
Other namespara-Methoxymethcathinone; 4-Methoxymethcathinone; bk-PMMA; PMMC; Methoxyphedrine; 4-MeOMC
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 26.2 ± 0.7 hours[ citation needed ]
Identifiers
  • (RS)-1-(4-Methoxyphenyl)-2-(methylamino)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.209.920 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H15NO2
Molar mass 193.246 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • O=C(c1ccc(OC)cc1)C(NC)C
  • InChI=1S/C11H15NO2/c1-8(12-2)11(13)9-4-6-10(14-3)7-5-9/h4-8,12H,1-3H3 Yes check.svgY
  • Key:MQUIHBQDYYAEMH-UHFFFAOYSA-N Yes check.svgY
   (verify)

Methedrone (para-methoxymethcathinone, 4-methoxymethcathinone, bk-PMMA, PMMC, methoxyphedrine, 4-MeOMC) is a recreational drug of the cathinone chemical class. [2] Chemically, methedrone is closely related to para-methoxymethamphetamine (PMMA), methylone and mephedrone. Methedrone received media attention in 2009 after the death of two young Swedish men. In both cases toxicology analysis showed methedrone was the only drug present in both men during the time of their overdose and subsequent deaths. [3] [4]

Contents

Uses

Dosage

There is little information available about how Methedrone is dosed. According to users, a single dose of Methedrone varies from 50 to 500 mg with effects lasting 45 minutes to two hours. There are at least two cases known of fatal intoxications with Methedrone. In the first case, the postmortem femoral blood sample of the patient contained a concentration of 8.4 μg/g Methedrone, the patient died 16 hours after consumption (with polysubstance use detected). In the second body the concentration in the femoral blood sample was 9.6 μg/g, with Methedrone being the only toxic compound detected. The scientific investigation [3] of these cases suggests that the Methedrone alone was responsible for these deaths and that the concentrations in the femoral blood represent the fatal levels of methedrone. These studies show that the therapeutic index (or safety ratio) is low compared to other illegal drugs like Amphetamine. A fatal dose is likely to be around 8 μg/g whereas the dose among users varies from 0.1 to 4.8 μg/g blood according to studies. [3]

Adverse effects

Anecdotal and case reports of human use of "bath salts", such as methedrone, suggest that these substances produce powerful psychological effects. These psychological effects include psychotic behavior, paranoia, delusions, hallucinations and also self-injury. [5]

There is very little known of the physical effects of methedrone in humans, but there have been some studies to the effects of methedrone in animals, so we[ who? ] focused on the effects in mice.

Studies to the effects of methedrone in mice show that methedrone produces a significant increase in circling, beam breaks and hyperactivity. Furthermore, the mice also showed a significant increase in salivation, head weaving and stimulation. Methedrone is currently a legal drug in many jurisdictions, however studies show that it shares major pharmacological properties with drugs that have been banned, such as mephedrone and methylone. Also, the effects of Methedrone are very similar to the effects of banned drugs in mice. [5] This suggests that Methedrone may be just as harmful as most commonly found Illicit drugs.

The health risks associated with methedrone are mostly unknown, but are expected to be similar to other cathinones. [6] Methedrone was almost immediately withdrawn from sale by initial vendors after reports of adverse health effects.[ citation needed ] Some amphetamine analogs containing a para-methoxy group are known to cause severe hyperthermia and even death due to concurrent MAOI and monoamine releasing action. [7]

Overdose

The deaths of two young men in southeast Sweden in 2009 were attributed to methedrone overdose. [3] [8]

Both were comatose when found. One suffered cardiorespiratory arrest on the way to the hospital, while the second survived for 16 hours in the emergency department.

Acute toxicity

There is little research regarding the toxicity of methedrone. Research has been done by animal-testing on mice once. [5] Also, the lethal doses found in the two Swedish methedrone-victims have been compared to the methedrone concentrations in the blood of two other males dying in similar conditions. [3]

The mean of the methedrone concentrations in the blood of the two deceased was 1.3 μg/g blood. One of these victims had a very high concentration of Methedrone in the blood, approximately 4.8 μg/g blood. The mean of the concentrations found in the blood of the deceased victims was 8.0 μg/g blood. None of the non-lethal doses or lethal doses is known, suggesting that the safety gap between a lethal and non-lethal dose of methedrone is probably very small, thus making use of this drug dangerous because poisonings, and simultaneously death, are accidental. [3]

In a study of the effects of synthetic cathiones in ‘bath salts’ the effects of methedrone on mice were tested, these effects were compared to the effects of cocaine and methamphetamine. Different tests were performed to get insight into motor coordination, balance and overall behavioral effects. The mice did not show any difference in motor coordination or balance (doses administered were 10.0 mg/kg and 30.0 mg/kg). However significant changes were shown in overall behavioral effects. Administration of methedrone led to: [5]

These effects are related with addiction potential. [9] [10] Excessive salivation is not an effect that is typically reported in humans. It is suggested that methedrone increases salivation via brain systems that primarily regulate autonomic responses. [3]

Compared with mephedrone, methylenedioxypyrovalerone (MDPV) and 4-fluoromethcathinone (4-FMC), methedrone has a relatively slow onset. Thereby increasing the risk; because effects are not immediately shown, this could lead to an accidental overdose. It could also make the drug less popular, because humans tend to favor drugs that cause large, rapid initial increases in locomotor activity. [5]

Chronic toxicity

Even in comparison with acute toxicity, chronic toxicity is poorly researched. Only the post-mortem study did little investigation on this subject. The findings of this study only showed that hair of the deceased victims contained methedrone, however, no conclusions were made regarding these findings. [3]

No studies have examined the effect of methedrone use during or before pregnancy by a pregnant female on the embryo, nor is the carcinogenicity researched.

Pharmacology

Mechanism of action

Methedrone has been found to be a potent serotonin transporter (SERT) and norepinephrine transporter (NET) inhibitor, but a weak dopamine transporter (DAT) inhibitor. Clinically, the DAT/SERT ratio of methedrone is less than one. Other analog compounds commonly have a DAT/SERT ratio less than half, meaning unlike other MDMA-like compounds methedrone does not prefer inhibition of the NET and DAT over the SERT. The resulting lack of inhibition despite its proclivity to release DAT can lead to a life-threatening adrenergic storm. Methedrone's high selectivity for SERT places it among the highest selectivity when compared to structurally similar compounds. [11]

Methedrone induces the transportation mediated release of NE, DA and 5-HT from cells preloaded with monoamines making it a serotonin–norepinephrine–dopamine (SNDRA) releasing agent, also known as triple releasing agent (TRA), which is a common characteristic among drugs of abuse. [11]

It has been found that methedrone is similar to MDMA in terms of the monoamine transporter interactions but an in vivo study of the drug resulted in a stronger hyperthermic reaction than what is normally reported in studies of MDMAs. Methedrone's affects on the serotonin transporter, SERT, can interfere and cause complications in individuals co-administering with serotonin altering medications such as selective serotonin reuptake inhibitors (SSRIs). [11]

Pharmacokinetics

To consider how methedrone (4-MeOMC) acts in a biological system, it is necessary to study the stability in an aqueous solution. Because, when tested directly in blood or urine, it is not known whether the compound will be degraded by enzymes available in the biological solutions or cause the chemical mechanisms, such as pH or dissolved oxygen. The length of the half-life of the compound has been examined and the percent remaining after 12 hours in buffers with various pHs. The tested pHs were 4, 7, 10 and 12. [12]

The conclusions are that methedrone, just as most analogs, is stable in acid solutions. However, in neutral and basic solutions it is decomposed, where a stronger decomposing takes place as the solution turns more basic.

When comparing methedrone with its analogs, it has been found that there are several factors which affect their stability:

Methedrone and four other analogs have their groups substituted in the meta- or para-positions. For these compounds the rate constant, k, has been determined and a Hammett plot was constructed by plotting the decomposition rate constant (0.693/half-life) in the pH of 12 against their Hammett constants, taken from literature. This again shows that methedrone is a relatively stable compound even in basic solution.

Another conclusion based on the results from the literature is that there is negative charge built up in the transition state during the rate determining step. This reasoning is based on the good linear correlation (r=0.9805) and the positive slope (determined as 1.76). [12]

There are two possible metabolites known for methedrone: [13]

Chemistry

Structure

Methedrone is a synthetic cathinone. It is related to the parent compound cathinone. Methedrone belongs to the phenethylamine family due to the presence of the cyclic group of atoms C 6 H 5 in which six carbons bind to form a hexagonal ring with five hydrogens each bonding to a carbon and the remaining carbon bonded to an atom or group of atoms other than hydrogen. [14] [15] [16]

Synthesis

Figure 1: Synthesis of methedrone Synthesis Methedrone.png
Figure 1: Synthesis of methedrone

The synthesis of methedrone is described in figure 1. and can be written as the following steps:

  1. Bromination of 1-(4-methoxyphenyl)propan-1-one to 2-bromo-1-(4-methoxyphenyl)propan-1-one.
  2. A reaction with methylamine in which the 2-bromo-1-(4-methoxyphenyl)propan-1-one becomes 1-(4-methoxyphenyl)-2-(methylamino)propan-1-ol.
  3. The final step is a reaction with potassium permanganate.

The synthesis of mephedrone, a structurally similar compound with only one less ether group than methedrone, is well documented. [17]

Reactivity

There are no articles found about the reactivity of methedrone.[ citation needed ]

History

The synthesis of methedrone was first reported in 1933. [18]

Society and culture

Names

Methoxyphedrine is the generic name of the drug and its INN Tooltip International Nonproprietary Name. [19]

Recreational use

Methedrone is a research chemical and its euphoric and stimulant properties can be abused. Similarly to MDMA it can be administered through insufflation, ingestion, smoking, rectal, and intravenous routes; however, it differs greatly in both duration and toxicity and great care should be taken when used due to the lack of medical literature available common among designer drugs. [20]

Its sale has been banned in Sweden since December 9, 2009. [3]

It is a controlled substance in China since October 1, 2015. [21]

Methedrone can be purchased legally in Europe (excluding Sweden) and in most states in the US on the Internet, but also it can also be found at head shops and other retailers. [22] It is, along with other new or unregulated synthetic drugs and research chemicals, commonly labeled as a "bath salt". [20]

Other animals

Mice

Methedrone has been found to have an effect on the overall behavior of mice which includes: [5]

Related Research Articles

<span class="mw-page-title-main">Reuptake</span> Reabsorption of a neurotransmitter by a neurotransmitter transporter

Reuptake is the reabsorption of a neurotransmitter by a neurotransmitter transporter located along the plasma membrane of an axon terminal or glial cell after it has performed its function of transmitting a neural impulse.

<span class="mw-page-title-main">Phenethylamine</span> Organic compound, a stimulant in humans

Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons. To a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentation.

<span class="mw-page-title-main">Empathogen</span> Class of psychoactive drugs that produce empathic experiences

Empathogens or entactogens are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, relatedness, emotional openness—that is, empathy or sympathy—as particularly observed and reported for experiences with 3,4-methylenedioxymethamphetamine (MDMA). This class of drug is distinguished from the classes of hallucinogen or psychedelic, and amphetamine or stimulants. Major members of this class include MDMA, MDA, MDEA, MDOH, MBDB, 5-APB, 5-MAPB, 6-APB, 6-MAPB, methylone, mephedrone, GHB, αMT, and αET, MDAI among others. Most entactogens are phenethylamines and amphetamines, although several, such as αMT and αET, are tryptamines. When referring to MDMA and its counterparts, the term MDxx is often used. Entactogens are sometimes incorrectly referred to as hallucinogens or stimulants, although many entactogens such as ecstasy exhibit psychedelic or stimulant properties as well.

<span class="mw-page-title-main">Methylone</span> Group of stereoisomers

Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.

<span class="mw-page-title-main">Methylenedioxypyrovalerone</span> Chemical compound

Methylenedioxypyrovalerone is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI). It was first developed in the 1960s by a team at Boehringer Ingelheim. Its activity at the dopamine transporter is six times stronger than at the norepinephrine transporter and it is virtually inactive at the serotonin transporter. MDPV remained an obscure stimulant until around 2004 when it was reportedly sold as a designer drug. In the US, products containing MDPV and labeled as bath salts were sold as recreational drugs in gas stations, similar to the marketing for Spice and K2 as incense, until it was banned in 2011.

<span class="mw-page-title-main">Mephedrone</span> Synthetic stimulant drug

Mephedrone, also known as 4-methylmethcathinone, 4-MMC, and 4-methylephedrone, is a synthetic stimulant drug belonging to the amphetamine and cathinone classes. It is commonly referred to by slang names such as drone, M-CAT, White Magic, meow meow, and bubble. Chemically, it is similar to the cathinone compounds found in the Khat plant, native to eastern Africa.

<span class="mw-page-title-main">Nisoxetine</span> Chemical compound

Nisoxetine, originally synthesized in the Lilly research laboratories during the early 1970s, is a potent and selective inhibitor for the reuptake of norepinephrine (noradrenaline) into synapses. It currently has no clinical applications in humans, although it was originally researched as an antidepressant. Nisoxetine is now widely used in scientific research as a standard selective norepinephrine reuptake inhibitor. It has been used to research obesity and energy balance, and exerts some local analgesia effects.

<span class="mw-page-title-main">Monoamine releasing agent</span> Class of compounds

A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitters and hence enhanced signaling by those neurotransmitters. The monoamine neurotransmitters include serotonin, norepinephrine, and dopamine; monoamine releasing agents can induce the release of one or more of these neurotransmitters.

<span class="mw-page-title-main">Naphyrone</span> Substituted cathinone stimulant drug

Naphyrone, also known as O-2482 and naphthylpyrovalerone, is a substituted cathinone drug derived from pyrovalerone that acts as a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI), producing stimulant effects and has been reported as a novel designer drug. No safety or toxicity data is available on the drug.

<span class="mw-page-title-main">3-Fluoroamphetamine</span> Stimulant drug that acts as an amphetamine

3-Fluoroamphetamine is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin. It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine.

<span class="mw-page-title-main">Substituted cathinone</span> Class of chemical compounds

Substituted cathinones, or simply 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.

<span class="mw-page-title-main">Salicylmethylecgonine</span> Chemical compound

Salicylmethylecgonine, (2′-Hydroxycocaine) is a tropane derivative drug which is both a synthetic analogue and a possible active metabolite of cocaine. Its potency in vitro is around 10x that of cocaine, although it is only around three times more potent than cocaine when administered to mice Note however that the compound 2′-Acetoxycocaine would act as a prodrug to Salicylmethylecgonine in humans, and has a more efficient partition coefficient which would act as a delivery system and would circumvent this reason for a drop in potency. Salicylmethylecgonine also shows increased behavioral stimulation compared to cocaine similar to the phenyltropanes. The hydroxy branch renders the molecule a QSAR of a 10-fold increase over cocaine in its binding potency for the dopamine transporter & a 52-fold enhanced affinity for the norepinephrine transporter. It also has a reduced selectivity for the serotonin transporter though only due to its greater increase at NET binding; its SERT affinity being 4-fold increased compared to cocaine. However, in overall binding affinity it displaces ligands better across the board than cocaine in all monoamine categories.

<span class="mw-page-title-main">Bath salts (drug)</span> Recreational drug often superficially resembling true bath salts

Bath salts are a group of recreational designer drugs. The name derives from instances in which the drugs were disguised as bath salts. The white powder, granules, or crystals often resemble Epsom salts, but differ chemically. The drugs' packaging often states "not for human consumption" in an attempt to circumvent drug prohibition laws. Additionally, they may be described as "plant food", "powdered cleaner", or other products.

<span class="mw-page-title-main">3-Methylmethcathinone</span> Substituted cathinone designer drug

3-Methylmethcathinone (3-MMC), also known as metaphedrone, is a designer drug from the substituted cathinone family. 3-MMC is a monoamine transporter substrate that potently releases and inhibits the reuptake of dopamine and norepinephrine, as well as displaying moderate serotonin releasing activity. Unlike some synthetic cathinones, 3-MMC has been evaluated in at least one large mammal study.

Selective serotonin reuptake inhibitors, or serotonin-specific re-uptake inhibitor (SSRIs), are a class of chemical compounds that have application as antidepressants and in the treatment of depression and other psychiatric disorders. SSRIs are therapeutically useful in the treatment of panic disorder (PD), posttraumatic stress disorder (PTSD), social anxiety disorder, obsessive-compulsive disorder (OCD), premenstrual dysphoric disorder (PMDD), and anorexia. There is also clinical evidence of the value of SSRIs in the treatment of the symptoms of schizophrenia and their ability to prevent cardiovascular diseases.

<span class="mw-page-title-main">4-Methylcathinone</span> Stimulant designer drug

4-Methylcathinone, is a stimulant drug of the cathinone chemical class. It is a metabolite of the better known drug mephedrone (4-methylmethcathinone).

<span class="mw-page-title-main">4-Chloromethcathinone</span> Simulant drug of the cathinone class

4-Chloromethcathinone is a stimulant drug of the cathinone class that has been sold online as a designer drug.

<span class="mw-page-title-main">Mexedrone</span> Stimulant and entactogen drug

Mexedrone is a stimulant and an entactogen drug of the cathinone class that has been sold online as a designer drug. It is the alpha-methoxy derivative of Mephedrone.

<i>N</i>-Ethylhexedrone Stimulant of the cathinone class

N-Ethylhexedrone (also known as α-ethylaminocaprophenone, N-ethylnorhexedrone, hexen, and NEH) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) with IC50 values of 0.0978 and 0.0467 μM, respectively. N-Ethylhexedrone was first mentioned in a series of patents by Boehringer Ingelheim in the 1960s which led to the development of the better-known drug methylenedioxypyrovalerone (MDPV). Since the mid-2010s, N-ethylhexedrone has been sold online as a designer drug. In 2018, N-ethylhexedrone was the second most common drug of the cathinone class to be identified in Drug Enforcement Administration seizures.

<span class="mw-page-title-main">3-Chloromethcathinone</span> Stimulant designer drug

3-Chloromethcathinone (3-CMC), also known as clophedrone, is a synthetic substance belonging to the cathinone class of psychoactive compounds. It is very similar in structure to other methcathinone derivatives such as 3-MMC and 4-CMC. Unlike cathinone, which occurs naturally in the khat plant Catha edulis, 3-CMC is not found in nature and is solely produced through chemical synthesis.

References

  1. ↑ "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii (Dz.U. 2011 nr 105 poz. 614)". Internetowy System Aktów Prawnych. Retrieved 17 June 2011.
  2. ↑ "Cathinone and its analogues (e.g. mephedrone, methedrone, α- pyrrolidinovalerophenone)". World Anti-Doping Agency. Archived from the original on 2014-11-06.
  3. 1 2 3 4 5 6 7 8 9 Wikström M, Thelander G, Nyström I, Kronstrand R (November 2010). "Two fatal intoxications with the new designer drug methedrone (4-methoxymethcathinone)". Journal of Analytical Toxicology. 34 (9): 594–8. doi: 10.1093/jat/34.9.594 . PMID   21073814.
  4. ↑ "EMCDDA and Europol step up information collection on mephedrone". Drugnet Europe. No. online 69. January–March 2010. Retrieved May 21, 2018.
  5. 1 2 3 4 5 6 Marusich JA, Grant KR, Blough BE, Wiley JL (October 2012). "Effects of synthetic cathinones contained in "bath salts" on motor behavior and a functional observational battery in mice". Neurotoxicology. 33 (5): 1305–13. Bibcode:2012NeuTx..33.1305M. doi:10.1016/j.neuro.2012.08.003. PMC   3475178 . PMID   22922498.
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  12. 1 2 Tsujikawa K, Mikuma T, Kuwayama K, Miyaguchi H, Kanamori T, Iwata YT, Inoue H (July 2012). "Degradation pathways of 4-methylmethcathinone in alkaline solution and stability of methcathinone analogs in various pH solutions". Forensic Science International. 220 (1–3): 103–10. doi:10.1016/j.forsciint.2012.02.005. PMID   22402273.
  13. ↑ Mueller DM, Rentsch KM (February 2012). "Generation of metabolites by an automated online metabolism method using human liver microsomes with subsequent identification by LC-MS(n), and metabolism of 11 cathinones" (PDF). Analytical and Bioanalytical Chemistry. 402 (6): 2141–51. doi:10.1007/s00216-011-5678-8. PMID   22231510. S2CID   27846319.
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  15. ↑ "Technical Profile of Methedrone" (PDF). European Monitoring Centre for Drugs and Drug Addiction. Retrieved March 17, 2015.
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  18. ↑ Skita A (1933). "Eine neue Synthese von 1.2-Amino-ketonen". Chemische Berichte. 66 (6): 858–866. doi:10.1002/cber.19330660615.
  19. ↑ Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 791. ISBN   978-1-4757-2085-3 . Retrieved 30 August 2024.
  20. 1 2 Psychonaut Research Web Mapping Project, MDPV report, London, UK: Institute of Psychiatry, King's College London; 2009.
  21. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  22. ↑ DEA (Drug Enforcement Agency). Synthetic cathinones – DEA request for information posted 3/31/11; 2011 [retrieved 28.07.11].
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