Chemistry:Methylone

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Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an entactogen and stimulant drug of the amphetamine, cathinone, and benzodioxole families related to 3,4-methylenedioxymethamphetamine (MDMA; "ecstasy").[1][2][3] It is the β-keto or cathinone analogue of MDMA.[3][2] Methylone is usually taken orally, but is also used by other routes.[1][2]

The drug acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA).[1][4][5][6] It has much less activity at the vesicular monoamine transporter 2 (VMAT2) than MDMA[1][7] and may have less serotonergic neurotoxicity.[1][8][9][4] In contrast to certain other entactogens like MDMA, methylone does not appear to be a significant agonist of the serotonin 5-HT2 receptors.[1][9][10][11] Methylone is similar in its effects to MDMA, producing entactogenic effects and euphoria, but has a reputation of being gentler than MDMA and only lasts about half as long.[1][12] Side effects of methylone include tachycardia, hangover, and insomnia.[1] It may have reduced negative after-effects compared to MDMA.[1] Methylone's onset is about 0.5 hours and its duration is about 2 to 3 hours.[1][13]

Methylone was first synthesized by Peyton Jacob III and Alexander Shulgin in the mid-1990s[14] and was first described in the literature in 1996.[2][15] It was patented by Jacob and Shulgin as a potential antidepressant and antiparkinsonian agent, but was never developed or marketed for such uses.[2][15] Methylone was encountered as a designer and recreational drug by 2004 and has become a controlled substance in many countries.[3][2] Similarly to MDMA, it is being developed for the treatment of post-traumatic stress disorder (PTSD).[16][17][18]

Use and effects

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 drug discrimination tests in rodents. Methylone does not substitute for the stimulant amphetamine or for the hallucinogen DOM in animal drug discrimination tests.[19] 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.[20][21][7]

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:[12]

"[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.[22][23] The studies found that the effects of methylone were similar to or milder than those of MDMA.[22][23] 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.[22] The misuse potential of methylone, as measured by for instance drug liking responses, appeared to be similar to that of MDMA.[22] However it also has less off-target effects than MDMA which may be an advantage for medical applications.[24][22][25]

Interactions

Pharmacology

Pharmacodynamics

Methylone acts as a mixed releasing agent and reuptake inhibitor of serotonin, norepinephrine, and dopamine.[7][26] In comparison to MDMA, it has approximately 3-fold lower affinity for the serotonin transporter, while its affinity for the norepinephrine and dopamine transporters is similar.[7][26] Notably, methylone's affinity for the vesicular monoamine transporter 2 (VMAT2) is about 13-fold lower than that of MDMA.[7] 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 still has relatively robust releasing capabilities.[26]

In contrast to MDMA, methylone and its metabolites lack significant affinity for the serotonin 5-HT2A and 5-HT2C receptors and similarly do not activate the serotonin 5-HT2B receptor.[9][10][11] This may make methylone safer than MDMA, for instance in terms of long-term cardiac valvulopathy risk.[27][28][29] Methylone is inactive at the mouse and rat trace amine-associated receptor 1 (TAAR1).[30][11]

Methylone has been found to produce psychoplastogenic effects in preclinical research and showed greater effects than MDMA.[31]

Similarly to MDMA, methylone has been found to be a monoaminergic neurotoxin in animals.[8] It has specifically been found to produce serotonergic and dopaminergic neurotoxicity in rodents.[8] However, in one study, moderate doses of MDMA produced serotonergic neurotoxicity in rodents whereas methylone and mephedrone did not do so, suggesting that cathinones like methylone may be less neurotoxic than their corresponding amphetamine counterparts like MDMA.[9][4]

Monoamine release of methylone and related agents (EC50, nM)
Compound 5-HT NE DA Ref
Dextroamphetamine 698–1,765 6.6–7.2 5.8–24.8 [32][5]
Dextromethamphetamine 736–1,292 12.3–13.8 8.5–24.5 [32][4]
Cathinone 6,100–7,595 23.6–25.6 34.8–83.1 [33][34][35]
Methcathinone 2,592–5,853 22–26.1 12.5–49.9 [33][34][36][37][35]
MDC 966 394 370 [6]
Methylone (MDMC) 234–708 140–270 117–220 [4][5][38][39][6]
Mephedrone 118.3–122 58–62.7 49.1–51 [4][5][34][37][40]
Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs:[41][42]

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). Another metabolite is 3,4-dihydroxymethcathinone (HHMC).[6][11] 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).[43] 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.[13] The onset of action and duration of action of methylone in humans are 0.5 hours and 2.5 to 3.0 hours, respectively.[13]

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.[7]

History

Methylone was first synthesized by Peyton Jacob III and Alexander Shulgin in the mid-1990s.[14][2][15] This was after the publication of Shulgin's PiHKAL (1991), and so methylone is not included in this book.[44] However, it was subsequently included in The Shulgin Index (2011).[3] The drug was patented by Jacob and Shulgin as a potential antidepressant and antiparkinsonian agent, but was never developed or marketed.[2][15] This was the first time that methylone was described in the literature.[15] The drug was first described in the scientific literature by 1997.[19] Methylone was encountered as a designer and recreational drug by 2004.[3][2] It has become a controlled substance in many countries.[2]

Society and culture

Methylone in powder form

Names and 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.

Commercial distribution

Bottles of Explosion

Analysis of "Explosion" has confirmed that the active ingredient is methylone.[45] 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.[46] 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.[47][48]

United Kingdom

In the United Kingdom, 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 compound was banned immediately.[49]

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.[50] Methylone was first classified by Sveriges riksdags health ministry Statens folkhälsoinstitut as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (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).[51]

Canada

Although not listed as a Schedule 1[52] 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.[53] 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.[54]

United States

In October 2011, the DEA issued an emergency ban on methylone. It was made illegal to possess and distribute.[55][56] On April 4, 2013, the DEA placed methylone as a Schedule 1 substance under the CSA.[57]

  • 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.[58]
  • 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).[59]
  • 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.

Research

Post-traumatic stress disorder

Under the developmental code TSND-201, methylone is under development by Transcend Therapeutics for the treatment of post-traumatic stress disorder (PTSD).[16][17][18] As of July 2024, it is in phase 2 clinical trials for this indication.[16][17]

See also

  • Substituted methylenedioxyphenethylamine

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol 35 (5): 512–536. May 2021. doi:10.1177/0269881120920420. PMID 32909493. 
  2. ↑ 2.00 2.01 2.02 2.03 2.04 2.05 2.06 2.07 2.08 2.09 "The effects and risks associated to mephedrone and methylone in humans: A review of the preliminary evidences". Brain Res Bull 126 (Pt 1): 61–67. September 2016. doi:10.1016/j.brainresbull.2016.03.005. PMID 26995278. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "#93. Methylone". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. pp. 228–230. ISBN 978-0-9630096-3-0. https://archive.org/details/shulgin-index-vol-1/page/228/mode/1up?view=theater. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology 37 (5): 1192–1203. 2012. doi:10.1038/npp.2011.304. PMID 22169943. 
  5. ↑ 5.0 5.1 5.2 5.3 "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology 38 (4): 552–562. 2013. doi:10.1038/npp.2012.204. PMID 23072836. 
  6. ↑ 6.0 6.1 6.2 6.3 "Pharmacokinetic Profiles and Pharmacodynamic Effects for Methylone and Its Metabolites in Rats". Neuropsychopharmacology 42 (3): 649–660. February 2017. doi:10.1038/npp.2016.213. PMID 27658484. 
  7. ↑ 7.0 7.1 7.2 7.3 7.4 7.5 "Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines". European Journal of Pharmacology 381 (1): 63–69. September 1999. doi:10.1016/S0014-2999(99)00538-5. PMID 10528135. 
  8. ↑ 8.0 8.1 8.2 "Synthetic Cathinones and Neurotoxicity Risks: A Systematic Review". Int J Mol Sci 24 (7): 6230. March 2023. doi:10.3390/ijms24076230. PMID 37047201. 
  9. ↑ 9.0 9.1 9.2 9.3 "3,4-Methylenedioxy methamphetamine, synthetic cathinones and psychedelics: From recreational to novel psychotherapeutic drugs". Front Psychiatry 13. 2022. doi:10.3389/fpsyt.2022.990405. PMID 36262632. 
  10. ↑ 10.0 10.1 "Methylone is a rapid-acting neuroplastogen with less off-target activity than MDMA". Front Neurosci 18. 2024. doi:10.3389/fnins.2024.1353131. PMID 38389788. 
  11. ↑ 11.0 11.1 11.2 11.3 "Metabolites of the ring-substituted stimulants MDMA, methylone and MDPV differentially affect human monoaminergic systems". J Psychopharmacol 33 (7): 831–841. July 2019. doi:10.1177/0269881119844185. PMID 31038382. 
  12. ↑ 12.0 12.1 "Cathinone | Ask Dr. Shulgin Online". 3 June 2004. http://www.cognitiveliberty.org/shulgin/adsarchive/cathinone.htm. 
  13. ↑ 13.0 13.1 13.2 Cite error: Invalid <ref> tag; no text was provided for refs named PoyatosLoFaroBerardinelli2022
  14. ↑ 14.0 14.1 James W. Jesso (1 June 2023). "Entactogens, MDMA, and Bringing New Love Drugs To Market (with Matthew Baggott)". Adventures Through The Mind (Podcast). Retrieved 27 January 2025.
  15. ↑ 15.0 15.1 15.2 15.3 15.4 Jacob III P, Shulgin AT, "Novel N-Substituted-2-Amino-3',4'-Methylene-dioxypropiophenones", WO patent 9639133, published 1996-12-12
  16. ↑ 16.0 16.1 16.2 "Methylone - Transcend Therapeutics". 24 July 2024. https://adisinsight.springer.com/drugs/800072616. 
  17. ↑ 17.0 17.1 17.2 "Delving into the Latest Updates on Methylone with Synapse". 20 September 2024. https://synapse.patsnap.com/drug/2c777b7e3faf48f18fad88d817c0ec7f. 
  18. ↑ 18.0 18.1 Bayer, Max (5 December 2023). "PTSD treatment is on the cusp of a paradigm shift. This biotech hopes to Transcend the competition". https://www.fiercebiotech.com/biotech/budding-psychiatry-biotech-looks-transcend-ptsd-competition-sample-phase-2-data. 
  19. ↑ 19.0 19.1 "Cathinone: an investigation of several N-alkyl and methylenedioxy-substituted analogs". Pharmacology, Biochemistry, and Behavior (Elsevier BV) 58 (4): 1109–1116. December 1997. doi:10.1016/s0091-3057(97)00323-7. PMID 9408221. 
  20. ↑ "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). 1998. 
  21. ↑ "Methcathinone (MCAT) and 2-methylamino-1-(3,4 methylenedioxyphenyl)propan-1-one (MDMCAT) inhibit [3H]serotonin uptake into human platelets". Am. Chem. Soc. Div. Med. Chem. Abs. 215 (152). 1998. 
  22. ↑ 22.0 22.1 22.2 22.3 22.4 "Pharmacological effects of methylone and MDMA in humans". Frontiers in Pharmacology 14. 2023. doi:10.3389/fphar.2023.1122861. PMID 36873994. 
  23. ↑ 23.0 23.1 "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. August 2021. doi:10.3390/biology10080788. PMID 34440023. 
  24. ↑ "Methylone, a rapid acting entactogen with robust anxiolytic and antidepressant-like activity". Frontiers in Psychiatry 13. 2022. doi:10.3389/fpsyt.2022.1041277. PMID 36704743. 
  25. ↑ "Methylone is a rapid-acting neuroplastogen with less off-target activity than MDMA". Frontiers in Neuroscience 18. 2024-02-07. doi:10.3389/fnins.2024.1353131. PMID 38389788. 
  26. ↑ 26.0 26.1 26.2 "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology 559 (2–3): 132–137. March 2007. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101. 
  27. ↑ "The risk of chronic psychedelic and MDMA microdosing for valvular heart disease". J Psychopharmacol 37 (9): 876–890. September 2023. doi:10.1177/02698811231190865. PMID 37572027. 
  28. ↑ "Microdosing psychedelics and the risk of cardiac fibrosis and valvulopathy: Comparison to known cardiotoxins". J Psychopharmacol 38 (3): 217–224. March 2024. doi:10.1177/02698811231225609. PMID 38214279. 
  29. ↑ "Serotonergic drugs and valvular heart disease". Expert Opin Drug Saf 8 (3): 317–329. May 2009. doi:10.1517/14740330902931524. PMID 19505264. 
  30. ↑ "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther 357 (1): 134–144. April 2016. doi:10.1124/jpet.115.229765. PMID 26791601. https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA. 
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  32. ↑ 32.0 32.1 "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse 39 (1): 32–41. January 2001. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707. 
  33. ↑ 33.0 33.1 Cite error: Invalid <ref> tag; no text was provided for refs named Blough2008
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  35. ↑ 35.0 35.1 "Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones". Neuropharmacology 245. March 2024. doi:10.1016/j.neuropharm.2023.109827. PMID 38154512. 
  36. ↑ Shalabi, Abdelrahman R. (14 December 2017). Structure-Activity Relationship Studies of Bupropion and Related 3-Substituted Methcathinone Analogues at Monoamine Transporters. VCU Scholars Compass (Thesis). doi:10.25772/M4E1-3549. Retrieved 24 November 2024.
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  38. ↑ Sakloth, Farhana (11 December 2015). Psychoactive synthetic cathinones (or 'bath salts'): Investigation of mechanisms of action. VCU Scholars Compass (Thesis). doi:10.25772/AY8R-PW77. Retrieved 24 November 2024.
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  43. ↑ "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. August 2006. doi:10.1080/00498250600780191. PMID 16891251. 
  44. ↑ PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. 1991. ISBN 978-0-9630096-0-9. OCLC 25627628. https://www.erowid.org/library/books_online/pihkal/. 
  45. ↑ "Methylone sold under "Explosion" and "Inpact" brand names in the Netherlands and Japan". Apr 2005. http://www.erowid.org/chemicals/methylone/methylone_info1.shtml. 
  46. ↑ "Evaluation of a procedure to assess the adverse effects of illicit drugs". Regulatory Toxicology and Pharmacology (Elsevier BV) 39 (1): 1–4. February 2004. doi:10.1016/j.yrtph.2003.09.001. PMID 14746774. 
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  49. ↑ "Suspected mephedrone-type compound seized at airport". BBC News. 1 April 2010. https://news.bbc.co.uk/1/hi/uk/8599814.stm. 
  50. ↑ "Läkemedelsverkets föreskrifter - LVFS och HSLF-FS". Läkemedelsverket - Swedish Medical Products Agency. http://www.lakemedelsverket.se/upload/lvfs/LVFS_2010_23.pdf. 
  51. ↑ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor;" (in sv). http://www.notisum.se/rnp/sls/sfs/20050733.pdf. 
  52. ↑ "Controlled Drugs and Substances Act: Legislative history · Schedule I · Section 19: Tramadol [Proposed; Amphetamines"]. http://isomerdesign.com/Cdsa/schedule.php?schedule=1&section=18.5&structure=C. 
  53. ↑ "Controlled Drugs and Substances Act: Definitions and Interpretations". http://isomerdesign.com/Cdsa/definitions.php?structure=C. 
  54. ↑ "The Safe Streets and Communities Act Four Components Coming into Force". 18 October 2012. http://www.justice.gc.ca/eng/news-nouv/nr-cp/2012/doc_32759.html. 
  55. ↑ "Chemicals Used in 'Bath Salts' Now Under Federal Control and Regulation". USA Dept of Justice. https://www.justice.gov/dea/divisions/hq/2011/hq102111.shtml. 
  56. ↑ "Schedules of Controlled Substances: Placement of Methylone Into Schedule I". http://www.deadiversion.usdoj.gov/fed_regs/rules/2012/fr1017.htm. 
  57. ↑ "Schedules of Controlled Substances: Placement of Methylone Into Schedule I". 2014-04-12. https://www.federalregister.gov/articles/2013/04/12/2013-08673/schedules-of-controlled-substances-placement-of-methylone-into-schedule-i. 
  58. ↑ "Florida Synthetic Drug Scheduling Actions - 2011-2014". http://myfloridalegal.com/webfiles.nsf/WF/RMAS-98NQAK/$file/History-of-AGs-Scheduling-Actions.pdf. 
  59. ↑ "Welcome to the Tennessee Secretary of State's Website – Tennessee Secretary of State". http://state.tn.us/sos/acts/107/pub/pc0169.pdf. 



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