Methylone

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Summary sheet: Methylone
Methylone
Molecular structure of Methylone
Methylone.svg
Chemical Nomenclature
Common names Methylone, bk-MDMA, M1, MDMC
Substitutive name 3,4-Methylenedioxy-N-methylcathinone
Systematic name (RS)-1-(Benzo[d][1,3]dioxol-5-yl)-N-methylpropan-2-amine
Class Membership
Psychoactive class Stimulant / Entactogen
Chemical class Cathinone
Routes of Administration

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.



Oral
Dosage
Threshold 75 mg
Light 75 - 150 mg
Common 150 - 225 mg
Strong 225 - 325 mg
Heavy 325 mg +
Duration
Total 2.5 - 4 hours
Onset 15 - 45 minutes
Peak 60 - 90 minutes
Offset 60 - 90 minutes
After effects 6 - 24 hours









DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.

3,4-Methylenedioxy-N-methcathinone (also known as M1, MDMC, βk-MDMA, and Methylone) is an entactogenic and stimulant substance of the cathinone chemical class that produces a mixture of entactogenic, stimulating, and euphoric effects when administered. It was first synthesized by chemists Peyton Jacob III and Alexander Shulgin in 1996 for potential use as an antidepressant.[1]

This compound is often 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."[2]

Chemistry

Methylone, or 3,4-methylenedioxy-N-methylcathinone, is a synthetic molecule of the cathinone family. 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.

Pharmacology

Methylone acts as a mixed reuptake inhibitor/releasing agent of serotonin, norepinephrine, and dopamine.[3][4] These neurotransmitters are thought to be responsible for regulating pleasure, motivation, focus, and sense of well-being. This is done by inhibiting the reuptake and reabsorption of the neurotransmitters after they have performed their function of transmitting a neural impulse, allowing them to accumulate and be reused, which results stimulating and euphoric effects.

In comparison to MDMA, it has approximately 3x lower affinity for the serotonin transporter (Ki=242.1 nM for methylone to Ki=72 nM for MDMA) while its affinity for the norepinephrine and dopamine transporters is similar.[5][6] Notably, methylone's affinity for the vesicular monoamine transporter 2 (VMAT2) is about 13x lower than that of MDMA.[7]

The result of these differences in pharmacology relative to MDMA are that methylone is less potent in terms of dose, has more balanced catecholaminergic relative to serotonergic effects, and behaves more like a reuptake inhibitor such as methylphenidate rather than a releaser like amphetamine; however, methylone still has relatively robust releasing capabilities.[8]

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 bk-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 bk-MDEA and bk-MBDB have become the established names for those substances.

Subjective effects

The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects should be taken with a grain of salt and will rarely (if ever) occur all at once, but heavier doses will increase the chances and are more likely to induce a full range of effects. Likewise, adverse effects become much more likely on higher doses and may include injury or death.

Physical effects
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Cognitive effects
User.svg

After effects
Aftereffects (3).svg

Experience reports

There are currently no anecdotal reports which describe the effects of this compound within our experience index. Additional experience reports can be found here:

Toxicity and harm potential

The toxicity and long-term health effects of recreational methylone use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown. This is because methylone has a very limited history of human usage.

Anecdotal evidence from people who have tried methylone within the community suggests that there do not seem to be any negative health effects attributed to simply trying it at low to moderate doses by itself and using it sparingly (but nothing can be completely guaranteed).

It is strongly recommended that one use harm reduction practices when using this substance.

Tolerance and addiction potential

As with other stimulants, the chronic use of methylone can be considered moderately addictive with a high potential for abuse and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and withdrawal effects may occur if a person suddenly stops their usage.

Tolerance to many of the effects of methylone develops with prolonged and repeated use. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about 1 - 3 weeks for the tolerance to be reduced to half and 3 - 6 weeks to be back at baseline (in the absence of further consumption). Methylone presents cross-tolerance with all dopaminergic stimulants, meaning that after the consumption of methylone all stimulants will have a reduced effect.

Psychosis

Main article: Stimulant psychosis

Abuse of compounds within the stimulant class at high dosages for prolonged periods of time can potentially result in a stimulant psychosis that may present with a variety of symptoms (e.g., paranoia, hallucinations, or delusions).[9] A review on treatment for amphetamine, dextroamphetamine, and methamphetamine abuse-induced psychosis states that about 5–15% of users fail to recover completely.[10][11] The same review asserts that, based upon at least one trial, antipsychotic medications effectively resolve the symptoms of acute amphetamine psychosis.[12] Psychosis very rarely arises from therapeutic use.[13][14]

Dangerous interactions

Although many psychoactive substances are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

Serotonin syndrome risk

Combinations in the list below may increase the amount of neurotransmitters such as serotonin and dopamine to dangerous or even fatal levels.

Legal status

  • Brazil - Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.[16]
  • Netherlands: In the Netherlands, methylone is covered under the medicine act. Because methylone is not registered officially, as such, it is forbidden to trade in methylone.[17]
  • 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.[citation needed]
  • United Kingdom: In the U.K., methylone has been illegal since the 16/04/2010 revision of the Misuse of Drugs Act.[citation needed]
  • Sweden: Methylone has been listed as a Schedule I narcotic in Sweden as of Oct 1 of 2010.[18]
  • Canada: Although not listed as a Schedule 1[19] 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.[20]
  • United States: As of October 21, 2011, the DEA has issued an emergency ban on methylone. It is illegal to possess and distribute.[21][22]
  • Germany: On July 26, 2012, methylone was added to Germany's controlled substance act ("BtMG"), making it illegal to produce, sell or possess.[23]

See also

External links

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. 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
  16. http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
  17. van Amsterdam et al., 2004
  18. http://www.lakemedelsverket.se/upload/lvfs/LVFS_2010_23.pdf
  19. http://isomerdesign.com/Cdsa/schedule.php?schedule=1&section=18.5&structure=C
  20. http://isomerdesign.com/Cdsa/definitions.php?structure=C
  21. "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
  22. "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
  23. 26. BtMÄndVO in Kraft getreten | http://www.buzer.de/gesetz/10254/index.htm