Methylone

Last updated
Methylone
Methylone.svg
MDMC-3d-sticks.png
Clinical data
Other names3,4-Methylenedioxy-N-methylcathinone; Methylenedioxymethcathinone; MDMC; β-Keto-MDMA; βk-MDMA; M1
Routes of
administration 		Common: oral, insufflation
Uncommon: IV or IM injection, rectal
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Onset of action 0.5 hours [3]
Elimination half-life 5.8–6.9 hours [3]
Duration of action 2.5–3.0 hours [3]
Identifiers
  • 1-(1,3-Benzodioxol-5-yl)-2-(methylamino)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H13NO3
Molar mass 207.229 g·mol−1
3D model (JSmol)
Solubility in water 357 mg/mL (20 °C)
  • CC(NC)C(=O)C1=CC=C(OCO2)C2=C1
  • InChI=1S/C11H13NO3/c1-7(12-2)11(13)8-3-4-9-10(5-8)15-6-14-9/h3-5,7,12H,6H2,1-2H3 Yes check.svgY
  • Key:VKEQBMCRQDSRET-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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.

Contents

Methylone is a slight modification of 3,4-methylenedioxymethamphetamine (MDMA, also known as ecstasy). It was first synthesized by the chemists Peyton Jacob III and Alexander Shulgin in 1996 for potential use as an antidepressant. [4] Methylone has been sold for recreational use, taking advantage of the absence of legal prohibition of this compound in many countries.[ citation needed ]

Chemistry

Methylone is the substituted cathinone analogue of 3,4-methylenedioxymethamphetamine (MDMA) and the 3,4-methylenedioxy analog of methcathinone. The only structural difference of methylone with respect to MDMA is the substitution of 2 hydrogen atoms by 1 oxygen atom in the β position of the phenethylamine core, forming a ketone group. [5]

Effects

Resemblance to MDMA

Structural similarities between some amphetamine-like stimulants and their 3,4-methylenedioxy- derivatives. Left: amphetamine, methamphetamine and methcathinone. Right: MDA, MDMA, and methylone Comparisons md analogues.png
Structural similarities between some amphetamine-like stimulants and their 3,4-methylenedioxy- derivatives.
Left: amphetamine, methamphetamine and methcathinone.
Right: MDA, MDMA, and methylone

Methylone substitutes for MDMA in rats trained to discriminate MDMA from saline. Methylone does not substitute for amphetamine or for the hallucinogenic DOM in animals trained to discriminate between these drugs and saline. [6] Further, also in common with MDMA, methylone acts on monoaminergic systems. In vitro , methylone has one third the potency of MDMA at inhibiting platelet serotonin accumulation and about the same in its inhibiting effects on the dopamine and noradrenaline transporters. [7] [8] [5]

In spite of these behavioral and pharmacological similarities between methylone and MDMA, the observed subjective effects of both drugs are not completely identical. Alexander Shulgin wrote of the former: [9]

"[Methylone] has almost the same potency of MDMA, but it does not produce the same effects. It has an almost antidepressant action, pleasant and positive, but not the unique magic of MDMA."

In acute pharmacological studies of methylone (50–300 mg) in humans, the drug produced physiological and psychological effects including increased blood pressure, heart rate, body temperature, pupil dilation, stimulation, euphoria, feelings of well-being, enhanced empathy, increased sociability, and altered perception. [10] [11] The studies found that the effects of methylone were similar to or milder than those of MDMA. [10] [11] Methylone had a faster onset of action and its subjective effects wore off sooner than MDMA, which might lead to a redosing pattern of use. [10] The misuse potential of methylone, as measured by for instance drug liking responses, appeared to be similar to that of MDMA. [10] However it also has less off-target effects than MDMA which may be an advantage for medical applications. [12] [13] [14]

Pharmacology

Pharmacodynamics

Methylone acts as a mixed reuptake inhibitor and releasing agent of serotonin, norepinephrine, and dopamine. [5] [15] In comparison to MDMA, it has approximately 3x lower affinity for the serotonin transporter, while its affinity for the norepinephrine and dopamine transporters is similar. [5] [15] Notably, methylone's affinity for the vesicular monoamine transporter 2 (VMAT2) is about 13x lower than that of MDMA. [5] The results of these differences in pharmacology relative to MDMA are that methylone is less potent in terms of dose, has more balanced catecholaminergic effects relative to serotonergic, and behaves more like a reuptake inhibitor like methylphenidate than a releaser like amphetamine; however, methylone has relatively robust releasing capabilities, [15] perhaps due to its ability to phosphorylate the monoamine transporters being similar in potency relative to MDMA.[ citation needed ]

Pharmacokinetics

The two major metabolic pathways in mammals for methylone are N-demethylation to methylenedioxycathinone (MDC), and demethylation followed by O-methylation of the 3- or 4-hydroxy group to 4-hydroxy-3-methoxymethcathinone (HMMC) or 3-hydroxy-4-methoxymethcathinone (3-OH-4-MeO-MC). When 5 mg/kg of methylone was administered to rats, it was found that around 26% was excreted as HMMC within the first 48 hours (less than 3% excreted unchanged). [16] The mean elimination half-lives of methylone in humans following oral administration of doses of 50 to 200 mg ranged from 5.8 to 6.9 hours. [3] The onset of action and duration of action of methylone in humans are 0.5 hours and 2.5 to 3.0 hours, respectively. [3]

Commercial distribution

Bottles of Explosion Bottle with methylone aka explosion.jpg
Bottles of Explosion

Analysis of "Explosion" has confirmed that the active ingredient is methylone. [17] [ unreliable source? ] Many other formulations marketed as household chemicals, as well as the pure powder, have been sold.

Netherlands

In the Netherlands, methylone is not yet listed under the Opium Law, but is covered under the medicine act. Because methylone is not registered officially, it is forbidden to trade in methylone. The Minister of Health has asked the Coordination point Assessment and Monitoring new drugs group (CAM) to gather information about this substance, resulting possibly in an official risk assessment. [18] Until now, no research has been conducted on the toxicity of methylone, so nothing is known about the harmfulness of this new drug.

New Zealand

In New Zealand, although methylone is not explicitly scheduled and falls outside the strict definitions of an "amphetamine analogue" in the Misuse of Drugs Act, it is considered to be "substantially similar" to methcathinone and is thus considered by law enforcement authorities to be a Class C illegal drug. Methylone was sold in New Zealand for around 6 months from November 2005 to April 2006 as an MDMA substitute, under the name "Ease". The product was withdrawn after legal disputes with the government. [19] [20]

UK

In the UK, methylone is illegal since the 16/04/2010 revision of the misuse of drugs act. Before this it was not specifically mentioned in United Kingdom (U.K.) law as the β-ketone was not covered under the Misuse of Drugs Act. In March 2010, plans were announced to make methylone and other cathinones, Class B drugs, "within weeks". While delayed by dissatisfaction in the Advisory Council on the Misuse of Drugs, the revision was rushed through by the government with little regard for the views of the council. The importation of the compounds was banned immediately. [21]

Sweden

Sveriges riksdag added methylone to schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of Oct 1, 2010, published by Medical Products Agency in their regulation LVFS 2010:23 listed as Metylon, 2-metylamino-1-(3,4-metylendioxifenyl)propan-1-on. [22] Methylone was first classified by Sveriges riksdags health ministry Statens folkhälsoinstitut  [ sv ] as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor  [ sv ] (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Nov 1, 2005, in their regulation SFS 2005:733 listed as 3,4-metylendioximetkatinon (Metylon). [23]

Canada

Although not listed as a Schedule 1 [24] substance, Health Canada reports that methylone falls under the scheduling as an analogue of amphetamine. However, Methylone bears the exact chemical difference between amphetamine and cathinone – and cathinone is listed as not being an analogue of amphetamine, possibly implying that methylone is unscheduled in Canada. [25] The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1; however, methylone was not added. [26]

United States

In October 2011, the DEA issued an emergency ban on methylone. It was made illegal to possess and distribute. [27] [28] On April 4, 2013, the DEA placed methylone as a Schedule 1 substance under the CSA. [29]

Effective February 16, 2012, methylenedioxymethcathinone (methylone) was classified as a dangerous drug, making it a felony to knowingly possess, use, possess for sale, manufacture, administer, transport for sale, import into the state, or offer to transport for sale or import into this state, sell, transfer or offer to sell or transfer. A.R.S. 13-3401(6)(c)(xliii), 2012 Ariz. Legis. Serv. Ch. 1 (H.B. 2356).
In January 2011, it was reported that Florida Attorney General Pam Bondi issued an emergency ban on MDPV, Methylone, Mephedrone, 3-methoxymethcathinone, 3-fluoromethcathinone, and 4-fluoromethcathinone as media attention on products labeled as "bath salts" grew. These chemicals are now Schedule I under Florida law. [30]
In January 2011, Louisiana Governor Bobby Jindal emergency scheduled 3,4-methylenedioxymethcathinone (methylone), 3,4-methyenedioxypyrovalerone (MDPV), 4-methylmethcathinone (mephedrone), 4-methoxymethcathinone (methedrone), 4-fluoromethcathinone (flephedrone), and 3-fluoromethcathinone (3-FMC).
On May 5, 2011, Tennessee Governor Bill Haslam signed a law making it a crime to knowingly produce, manufacture, distribute, sell, offer for sale or possess with intent produce, manufacture, distribute, sell, or offer for sale any product containing 3,4-methylenedioxymethcathinone (methylone), 3,4-methyenedioxypyrovalerone (MDPV), 4-methylmethcathinone (mephedrone), 4-methoxymethcathinone (methedrone), 4-fluoromethcathinone (flephedrone), and 3-fluoromethcathinone (3-FMC). [31]
In September 2011, Texas added 3,4-methylenedioxy-N-methylcathinone to the Penalty Group 2 listing of the Health and Safety Code. Possession of a substance in penalty group 2 is a minimum of a state jail felony.
Schedule 1 controlled substance in 2012.

Etymology

"Methylone" is also a trademarked brand name for an injectable form of methylprednisolone, a corticosteroid hormone used to treat arthritis and severe allergic reactions; hence, methylone may be confused with it. Aside from context, they can be distinguished by the fact that the name will usually be capitalized when referring to the prescription drug.

A proposed alternate name is βk-MDMA, or beta-keto-MDMA. While this nomenclature has not caught on because the name "methylone" became widely used before the conflicting Methylone trademark was noticed, the analogous names for related chemicals βk-MDEA and βk-MBDB have become the established names for those substances.

See also

Related Research Articles

<span class="mw-page-title-main">MDMA</span> Psychoactive drug, often called ecstasy

3,4-Methyl​enedioxy​methamphetamine (MDMA), commonly known as ecstasy, and molly or mandy, is a potent empathogen–entactogen with stimulant and minor psychedelic properties. Investigational indications include as an adjunct to psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder. The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours.

<span class="mw-page-title-main">Methcathinone</span> Psychoactive stimulant

Methcathinone is a monoamine alkaloid and psychoactive stimulant, a substituted cathinone. It is used as a recreational drug due to its potent stimulant and euphoric effects and is considered to be addictive, with both physical and psychological withdrawal occurring if its use is discontinued after prolonged or high-dosage administration. It is usually snorted, but can be smoked, injected, or taken orally.

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

Cathinone is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the main contributor to the stimulant effect of Catha edulis, also known as khat. Cathinone differs from many other amphetamines in that it has a ketone functional group. Other phenethylamines that share this structure include the stimulants methcathinone, MDPV, mephedrone and the antidepressant bupropion.

<span class="mw-page-title-main">3,4-Methylenedioxyamphetamine</span> Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylenedioxyamphetamine is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

<span class="mw-page-title-main">Butylone</span> Entactogen, psychedelic, and stimulant drug of the phenethylamine class

Butylone, also known as β-keto-N-methylbenzodioxolylbutanamine (βk-MBDB), is an entactogen, psychedelic, and stimulant psychoactive drug of the phenethylamine chemical class. It is the β-keto analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone.

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

Ethylone, also known as 3,4-methylenedioxy-N-ethylcathinone, is a recreational designer drug classified as an entactogen, stimulant, and psychedelic of the phenethylamine, amphetamine, and cathinone chemical classes. It is the β-keto analogue of MDEA ("Eve"). Ethylone has only a short history of human use and is reported to be less potent than its relative methylone. In the United States, it began to be found in cathinone products in late 2011.

<i>alpha</i>-Pyrrolidinopropiophenone Chemical compound

α-Pyrrolidinopropiophenone (α-PPP), is a stimulant drug. It is similar in structure to the appetite suppressant diethylpropion and has analogous effects in animals. Little is known about this compound, but it has been detected by laboratories in Germany as an ingredient in "ecstasy" tablets seized by law enforcement authorities. This drug has been found to produce stimulant effects in animals and presumably also produces these effects in humans, based on the context in which it has been found.

<span class="mw-page-title-main">Substituted methylenedioxyphenethylamine</span> Class of psychoactive drugs

The substituted methylenedioxyphenethylamines represent a diverse chemical class of compounds derived from phenethylamines. This category encompasses numerous psychoactive substances with entactogenic, psychedelic, and/or stimulant properties, in addition to entheogens. These compounds find application as research chemicals, designer drugs, and recreational substances.

<span class="mw-page-title-main">Methedrone</span> Chemical compound of the cathinone class

Methedrone is a recreational drug of the cathinone chemical class. 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.

<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 of the amphetamine and cathinone classes. Slang names include drone, M-CAT, White Magic, meow meow and bubble. It is chemically similar to the cathinone compounds found in the Khat plant of eastern Africa. It comes in the form of tablets or crystals, which users can swallow, snort or inject, producing effects similar to those of MDMA, amphetamines and cocaine.

<span class="mw-page-title-main">Ethcathinone</span> Simulant designer drug

Ethcathinone, also known as ethylpropion or ETH-CAT, 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. Ethcathinone has been identified as an ingredient in both quasi-legal "party pills", and, along with mephedrone, has also been reported as having been sold as "ecstasy" in the Australian city of Cairns.

<span class="mw-page-title-main">5-Methyl-MDA</span> Chemical compound

5-Methyl-3,4-methylenedioxyamphetamine (5-Methyl-MDA) is an entactogen and psychedelic designer drug of the amphetamine class. It is a ring-methylated homologue of MDA and a structural isomer of MDMA.

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

MDAI (5,6-methylenedioxy-2-aminoindane) is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) in vitro and produces entactogen effects in humans.

<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 a monoamine neurotransmitter from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitter. Many drugs induce their effects in the body and/or brain via the release of monoamine neurotransmitters, e.g., trace amines, many substituted amphetamines, and related compounds.

3,4-Methylenedioxy-<i>N</i>-ethylamphetamine Chemical compound

3,4-Methylenedioxy-N-ethylamphetamine is an empathogenic psychoactive drug. MDEA is a substituted amphetamine and a substituted methylenedioxyphenethylamine. MDEA acts as a serotonin, norepinephrine, and dopamine releasing agent and reuptake inhibitor.

Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).

<span class="mw-page-title-main">3,4-Dimethylmethcathinone</span> Designer stimulant drug

3,4-Dimethylmethcathinone (3,4-DMMC) 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. 3,4-DMMC has been seized as a designer drug in Australia. In vitro, 3,4-DMMC was shown to be a monoamine transporter substrate that potently inhibits norepinephrine and serotonin reuptake, and to a lesser extent dopamine reuptake.

A monoamine reuptake inhibitor (MRI) is a drug that acts as a reuptake inhibitor of one or more of the three major monoamine neurotransmitters serotonin, norepinephrine, and dopamine by blocking the action of one or more of the respective monoamine transporters (MATs), which include the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT). This in turn results in an increase in the synaptic concentrations of one or more of these neurotransmitters and therefore an increase in monoaminergic neurotransmission.

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 mislabeled as plant food, powdered cleaner, and other such products.

<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.

References

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  3. 1 2 3 4 5 Poyatos L, Lo Faro AF, Berardinelli D, Sprega G, Malaca S, Pichini S, et al. (November 2022). "Methylone and MDMA Pharmacokinetics Following Controlled Administration in Humans". International Journal of Molecular Sciences. 23 (23): 14636. doi: 10.3390/ijms232314636 . PMC   9736016 . PMID   36498963.
  4. ↑ WO 9639133,Jacob III P, Shulgin AT,"Novel N-Substituted-2-Amino-3',4'-Methylene-dioxypropiophenones",published 1996-12-12, assigned to Neurobiological Technologies Inc.
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  11. 1 2 Poyatos L, Papaseit E, Olesti E, Pérez-Mañá C, Ventura M, Carbón X, et al. (August 2021). "A Comparison of Acute Pharmacological Effects of Methylone and MDMA Administration in Humans and Oral Fluid Concentrations as Biomarkers of Exposure". Biology. 10 (8): 788. doi: 10.3390/biology10080788 . PMC   8389614 . PMID   34440023.
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  19. ↑ "Party pill sparks official concern". One News . 7 April 2006. Archived from the original on 9 February 2012. Retrieved 23 October 2011.
  20. ↑ "EASE trial terminated after conflicting advice". scoop.co.nz. April 9, 2006. Archived from the original on 2012-09-29.
  21. ↑ "Suspected mephedrone-type compound seized at airport". BBC News. 1 April 2010. Retrieved 3 April 2010.
  22. ↑ "Läkemedelsverkets föreskrifter - LVFS och HSLF-FS" (PDF). Läkemedelsverket - Swedish Medical Products Agency. Archived (PDF) from the original on 2011-02-16. Retrieved 2010-10-07.
  23. ↑ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor;" (PDF). notisum.se (in Swedish). Archived (PDF) from the original on 2016-03-04. Retrieved 2015-10-10.
  24. ↑ "Controlled Drugs and Substances Act : Legislative history · Schedule I · Section 19: Tramadol [Proposed]; Amphetamines". isomerdesign.com. Archived from the original on 10 November 2013. Retrieved 28 March 2018.
  25. ↑ "Controlled Drugs and Substances Act : Definitions and Interpretations". isomerdesign.com. Archived from the original on 10 November 2013. Retrieved 28 March 2018.
  26. ↑ "The Safe Streets and Communities Act Four Components Coming into Force". 18 October 2012. Archived from the original on 18 October 2012. Retrieved 28 March 2018.
  27. ↑ "Chemicals Used in 'Bath Salts' Now Under Federal Control and Regulation". USA Dept of Justice. Archived from the original on 25 April 2014. Retrieved 22 April 2014.
  28. ↑ "Schedules of Controlled Substances: Placement of Methylone Into Schedule I". usdoj.gov. Archived from the original on 17 April 2014. Retrieved 22 April 2014.
  29. ↑ "Schedules of Controlled Substances: Placement of Methylone Into Schedule I". federalregister.gov. 2014-04-12. Archived from the original on 15 December 2014. Retrieved 22 April 2014.
  30. ↑ "Florida Synthetic Drug Scheduling Actions - 2011-2014" (PDF). myfloridalegal.com. Archived (PDF) from the original on 2015-03-20. Retrieved 2017-04-08.
  31. ↑ "Welcome to the Tennessee Secretary of State's Website – Tennessee Secretary of State" (PDF). state.tn.us. Archived (PDF) from the original on 1 September 2013. Retrieved 28 March 2018.
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