Methylone

Source: Wikipedia, the free encyclopedia.
"MDMC" redirects here. For other uses, see MDMC (disambiguation).
Not to be confused with ethylone.
Methylone
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 action0.5 hours[3]
Elimination half-life5.8–6.9 hours[3]
Duration of action2.5–3.0 hours[3]
Identifiers
  • 1-(1,3-Benzodioxol-5-yl)-2-(methylamino)propan-1-one
JSmol)
Solubility in water357 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 checkY
  • Key:VKEQBMCRQDSRET-UHFFFAOYSA-N checkY
 ☒NcheckY (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.

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

See also: MDMA
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

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

phosphorylate the monoamine transporters being similar in potency relative to MDMA.[citation needed
]

Pharmacokinetics

The two major

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

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.

Legal status

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]

  • Arizona:
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).
  • Florida:
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]
  • Louisiana:
In January 2011, Louisiana Governor Bobby Jindal emergency scheduled 3,4-methylenedioxymethcathinone (methylone), 3,4-methyenedioxypyrovalerone (
3-FMC
).
  • Tennessee:
On May 5, 2011, Tennessee Governor
3-FMC).[31]
  • Texas:
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.
  • Michigan:
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-MBDB
have become the established names for those substances.

See also

References

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ "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.
  3. ^
    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. 
  5. ^
    PMID 10528135
    .
  6. S2CID 9704972
    .
  7. ^ Cozzi NV, Sievert MK, Shulgin AT, Jacob III P, Ruoho AE (1998). "Methcathinone and 2 methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one (methylone) selectively inhibit plasma membrane catecholamine reuptake transporters". Soc. Neurosci. Abs. 24 (341.8).
  8. ^ Cozzi NV, Shulgin AT, Ruoho AE (1998). "Methcathinone (MCAT) and 2-methylamino-1-(3,4 methylenedioxyphenyl)propan-1-one (MDMCAT) inhibit [3H]serotonin uptake into human platelets". Amer. Chem. Soc. Div. Med. Chem. Abs. 215 (152).
  9. ^ "Cathinone | Ask Dr. Shulgin Online". Archived from the original on 2010-04-13. Retrieved 2010-01-17.
  10. ^
    PMID 36873994
    .
  11. ^
    PMID 34440023
    .
  12. PMID 36704743
    .
  13. PMID 36873994
    .
  14. PMID 38389788
    .
  15. ^
    PMID 17223101
    .
  16. S2CID 10875717
    .
  17. ^ "Methylone sold under "Explosion" and "Inpact" brand names in the Netherlands and Japan". www.erowid.org. Apr 2005. Archived from the original on 2009-03-04.
  18. PMID 14746774
    .
  19. 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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