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Description

Methylone Also known as:

  • 1-(1,3-Benzodioxol-5-yl)-2-(methylamino)-1-propanon[German][ACD/IUPAC Name]
  • 1-(1,3-Benzodioxol-5-yl)-2-(methylamino)-1-propanone[ACD/IUPAC Name]
  • 1-(1,3-Benzodioxol-5-yl)-2-(méthylamino)-1-propanone[French][ACD/IUPAC Name]
  • 1-(1,3-Benzodioxol-5-yl)-2-(methylamino)propan-1-one
  • 1-Propanone, 1-(1,3-benzodioxol-5-yl)-2-(methylamino)-[ACD/Index Name]
  • 3,4-methylenedioxymethcathinone
  • bk-MDMA
  • L4I4B1R01F
  • METHYLONE, (+)-
  • UNII:L4I4B1R01F
  • (S)-2-METHYLAMIO-1-(3,4-METHYLENEDIOXYPHENYL)PROPAN-1-ONE
  • (S)-METHYLONE
  • 1-(Benzo[d][1,3]dioxol-5-yl)-2-(methylamino)propan-1-one
  • '186028-79-5
  • 2-METHYL AMINO-1-(3,4-METHYLENEDIOXYPHENYL) PROPAN-1-ONE
  • 2-methylamino-1-(3,4-methyl enedioxyphenyl)propan-1-one
  • 2-Methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one
  • Methylenedioxymethcathinone

βk-MDMA is a cathinone stimulant and empathogen, similar in structure to MDMA, though more stimulating and less empathogenic in comparison. Was very commonly mis-sold as MDMA on the street until it was banned in 2013. The Marquis reagent can differentiate βk-MDMA from MDMA. Less potent than MDMA with a slightly shorter duration.

Summary

Methylone was first synthesized by chemists Peyton Jacob III and Alexander Shulgin in 1996 as a potential antidepressant. Methylone is sometimes used as a substitute for MDMA due to similarities in their effects. Alexander Shulgin commented that the substances has "almost the same potency of MDMA, but it does not produce the same effects.

" He also stated that it “has an almost antidepressant action, pleasant and positive, but not the unique magic of MDMA. " The toxicity of methylone has not been well-studied, although it likely does not exceed that of MDMA, and it has a limited history of human usage. It is highly advised to use harm reduction practices if using this substance.

Chemistry

Methylone

Methylone

Cathinones are structurally similar to amphetamines, they contain a phenethylamine core featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain with an additional methyl substitution at Rα.

Cathinones such as methylone are alpha-methylated phenethylamines.

Cathinones differ from amphetamines by the addition of a ketone functional group, a carbonyl group at Rβ. Methylone contains an methyl substitution at RN, a substitution which is shared with MDMA, mephedrone, and certain other stimulants.

Methylone contains additional substitutions at R3 and R4 of the phenyl ring with oxygen groups.

These oxygen groups are incorporated into a methylenedioxy ring through a methylene chain.

Methylone shares this methylenedioxy ring with MDA, MDAI and MDMA.

Common NameMethylone
Systematic nameMethylone
FormulaC_{11}H_{13}NO_{3}
SMILESCC(C(=O)c1ccc2c(c1)OCO2)NC
Std. InChiInChI=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
Std. InChiKeyVKEQBMCRQDSRET-UHFFFAOYSA-N
Avg. Mass207.2258 Da
Molecular Weight207.2258
Monoisotopic Mass207.089539 Da
Nominal Mass207
ChemSpider ID21106350

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Dose Chart

Oral
Light100-150mg
Common150-250mg
Strong200-300mg
Heavy300+mg

Duration Chart

Methylone Duration Data
Onset15-60 minutes
Duration2-4 hours
After-effects6-24 hours

Interactions

Caution

  1. Mushrooms
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  2. LSD
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  3. DMT
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  4. Mescaline
    • The focus and anxiety caused by stimulants is magnified by psychedelics and results in an increased risk of thought loops
  5. 2C-x
    • The anxiogenic and focusing effects of stimulants increase the chance of unpleasant thought loops. The combination is generally uneccessary because of the stimulating effects of psychedelics. Combination of the stimulating effects may be uncomfortable.
  6. Cannabis
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  7. Ketamine
    • No unexpected interactions, though likely to increase blood pressure but not an issue with sensible doses. Moving around on high doses of this combination may be ill advised due to risk of physical injury.
  8. MXE
    • Risk of tachycardia, hypertension, and manic states
  9. Cocaine
    • This combination of stimulants will increase strain on the heart. It is not generally worth it as cocaine has a mild blocking effect on dopamine releasers like amphetamine
  10. Caffeine
    • This combination of stimulants is not generally necessary and may increase strain on the heart, as well as potentially causing anxiety and greater physical discomfort.
  11. Alcohol
    • Drinking on stimulants is risky because the sedative effects of the alcohol are reduced, and these are what the body uses to gauge drunkenness. This typically leads to excessive drinking with greatly reduced inhibitions, high risk of liver damage and increased dehydration. They will also allow you to drink past a point where you might normally pass out, increasing the risk. If you do decide to do this then you should set a limit of how much you will drink each hour and stick to it, bearing in mind that you will feel the alcohol and the stimulant less. Extended release formulations may severely impede sleep, further worsening the hangover.
  12. GHB/GBL
    • Stimulants increase respiration rate allowing a higher dose of sedatives. If the stimulant wears off first then the opiate may overcome the patient and cause respiratory arrest.
  13. Opioids
    • Stimulants increase respiration rate allowing a higher dose of opiates. If the stimulant wears off first then the opiate may overcome the patient and cause respiratory arrest.

Dangerous

  1. DOx
    • The combined stimulating effects of the two can lead to an uncomfortable body-load, while the focusing effects of amphetamine can easily lead to thought loops. Coming down from amphetamines while the DOx is still active can be quite anxiogenic.
  2. NBOMes
    • Amphetamines and NBOMes both provide considerable stimulation. When combined they can result in tachycardia, hypertension, vasoconstriction and in extreme cases heart failure. The anxiogenic and focusing effects of stimulants are also not good in combination with psychedelics as they can lead to unpleasant thought loops. NBOMes are known to cause seizures and stimulants can increase this risk.
  3. 2C-T-x
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences. In extreme cases, they can result in severe vasoconstriction, tachycardia, hypertension, and in extreme cases heart failure.
  4. 5-MeO-xxT
    • The anxiogenic and focusing effects of stimulants increase the chance of unpleasant thought loops. The combination is generally unnecessary because of the stimulating effects of psychedelics.
  5. DXM
    • Both substances raise heart rate, in extreme cases, panic attacks caused by these drugs have led to more serious heart issues.
  6. PCP
    • This combination can easily lead to hypermanic states

Low Synergy

  1. Benzodiazepines
    • Both can dull each other's effects, so if one wears off before the other it's possible to overdose due to the lack of counteraction

No Synergy

  1. SSRIs

High Synergy

  1. N2O
  2. MDMA
    • Amphetamines increase the neurotoxic effects of MDMA

Legal Status

  • Austria: Since June 26, 2019, methylone is illegal to possess, produce and sell under the SMG. (Suchtmittelgesetz Österreich)
  • Brazil: Methylone is illegal to possess, produce and sell as it is listed on Portaria SVS/MS nº 344.
  • Canada: Although not listed as a Schedule 1 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; cathinone is listed as not being an analogue of amphetamine leading to imply that methylone is unscheduled in Canada.
  • Germany: Methylone is controlled under Anlage II BtMG (Narcotics Act, Schedule II) as of July 26, 2012. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.
  • The Netherlands: Methylone is covered by the Medicine Act. Because methylone is not approved officially, it is forbidden to trade methylone.
  • 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.
  • Russia: Methyloneis classed as a Schedule I prohibited substance.
  • Sweden: Methylone has been listed as a Schedule I narcotic in Sweden as of October 1, 2010.
  • United Kingdom: Methylone is a Class B drug in the United Kingdom as a result of the cathinone catch-all clause.
  • United States: As of October 21, 2011, the DEA has issued an emergency ban on methylone. It is illegal to possess and distribute.
  • Sources

    References

    1. http://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=WO9639133
    2. "Cathinone | Ask Dr. Shulgin Online".
    3. Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/10528135
    4. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299906013811
    5. Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/10528135
    6. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299906013811
    7. Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/10528135
    8. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299906013811
    9. Treatment for amphetamine psychosis | [1]
    10. Treatment for amphetamine psychosis | [2]
    11. Hofmann FG (1983). A Handbook on Drug and Alcohol Abuse: The Biomedical Aspects (2nd ed.). New York: Oxford University Press. p. 329. ISBN 9780195030570.
    12. Treatment for amphetamine psychosis | [3]
    13. Stimulant Misuse: Strategies to Manage a Growing Problem | http://www.acha.org/prof_dev/ADHD_docs/ADHD_PDprogram_Article2.pdf
    14. http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021303s026lbl.pdf
    15. Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of Medical Toxicology, 5(2), 63-67. https://doi.org/10.1007/BF03161089
    16. Gillman, P. K. (2005). Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity. British Journal of Anaesthesia, 95(4), 434-441. https://doi.org/10.1093/bja/aei210
    17. https://www.ris.bka.gv.at/Dokumente/BgblAuth/BGBLA_2019_II_167/BGBLA_2019_II_167.pdfsig
    18. http://portal.anvisa.gov.br/documents/10181/3115436/(1)RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
    19. http://isomerdesign.com/Cdsa/schedule.php?schedule=1§ion=18.5&structure=C
    20. http://isomerdesign.com/Cdsa/definitions.php?structure=C
    21. "Anlage II BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 18, 2019.
    22. "Sechsundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (in German). Bundesanzeiger Verlag. Retrieved December 18, 2019.
    23. "§ 29 BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 18, 2019.
    24. van Amsterdam et al., 2004
    25. Resolution of the Government of the Russian Federation | https://www.consultant.ru/cons/cgi/online.cgi?req=doc&base=LAW&n=314201&fld=134&dst=100034,0&rnd=0.41568319511755825#047741519652799347
    26. http://www.lakemedelsverket.se/upload/lvfs/LVFS_2010_23.pdf
    27. United Kingdom. (2010). Misuse of Drugs Act 1971 (S.I. 2010/1207). London: The Stationery Office Limited. Retrieved February 9, 2018, from https://www.legislation.gov.uk/uksi/2010/1207/made
    28. "Chemicals Used in 'Bath Salts' Now Under Federal Control and Regulation". USA Dept of Justice. Retrieved 22 April 2014. | http://www.justice.gov/dea/divisions/hq/2011/hq102111.shtml
    29. "Schedules of Controlled Substances: Placement of Methylone Into Schedule I". Retrieved 22 April 2014. | http://www.deadiversion.usdoj.gov/fed_regs/rules/2012/fr1017.htm

    Information made possible with:

    1. PsychonautWiki is a community-driven online encyclopedia that aims to document the field of psychonautics in a comprehensive, scientifically-grounded manner.
    2. Erowid is a non-profit educational & harm-reduction resource with 60 thousand pages of online information about psychoactive drugs
    3. PubChem National Center for Bio Informatics
    4. Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
    5. Wikipedia

    Additional APIs were used to construct this information. Thanks to ChemSpider, NCBI, PubChem etc.

    Data is constantly updated so please check back later to see if there is any more available information on this substance.