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]
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 ketonegroup.[5]
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 (50–300mg) 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]
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.
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.
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]
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]
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]
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 3toSchedule 1; however, methylone was not added.[26]
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 (MDPV), 4-methylmethcathinone (mephedrone), 4-methoxymethcathinone (methedrone), 4-fluoromethcathinone (flephedrone), and 3-fluoromethcathinone (3-FMC).
Tennessee:
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]
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.
"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.
^ abcdeCozzi NV, Sievert MK, Shulgin AT, Jacob P, Ruoho AE (September 1999). "Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines". European Journal of Pharmacology. 381 (1): 63–69. doi:10.1016/S0014-2999(99)00538-5. PMID10528135.
^Dal Cason TA, Young R, Glennon RA (December 1997). "Cathinone: an investigation of several N-alkyl and methylenedioxy-substituted analogs". Pharmacology, Biochemistry, and Behavior. 58 (4). Elsevier BV: 1109–1116. doi:10.1016/s0091-3057(97)00323-7. PMID9408221. S2CID9704972.
^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).
^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).
^ abcNagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID17223101.
^Kamata HT, Shima N, Zaitsu K, Kamata T, Miki A, Nishikawa M, et al. (August 2006). "Metabolism of the recently encountered designer drug, methylone, in humans and rats". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 36 (8): 709–723. doi:10.1080/00498250600780191. PMID16891251. S2CID10875717.
^van Amsterdam JG, Best W, Opperhuizen A, de Wolff FA (February 2004). "Evaluation of a procedure to assess the adverse effects of illicit drugs". Regulatory Toxicology and Pharmacology. 39 (1). Elsevier BV: 1–4. doi:10.1016/j.yrtph.2003.09.001. hdl:10029/12622. PMID14746774.
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