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Methylone

Methylone
The skeletal formula of methylone
Methylone.png
Chemical Nomenclature
Common names Methylone
Substitutive name bk-MDMA, MDMC
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



Oral
Dosage
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.
DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation.
This dosage and duration information has been sourced from TripSit
Threshold 60 - 100 mg
Light 100 - 150 mg
Common 150 - 250 mg
Strong 200 - 300 mg
Heavy 300 mg +
Duration
Total 2 - 4 hours
Onset 15 - 60 minutes
Peak 60 - 90 minutes
Offset 60 - 120 minutes
After effects 6 - 24 hours









Summary sheet: Methylone

Methylone (also known as M1, 3,4-methylenedioxy-N-methylcathinone, MDMC and bk-MDMA) is an entactogen and stimulant of the phenethylamine, amphetamine and cathinone classes. 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 its similar range of subjective effects. However, in spite of behavioral and pharmacological similarities between methylone and MDMA, the observed subjective effects of both drugs are not completely identical. Alexander Shulgin wrote that the drug 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 ketone functional group, a carbonyl group at R1. 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 MDAI and MDMA.

Pharmacology

Methylone acts as a mixed reuptake inhibitor/releasing agent of serotonin, norepinephrine, and dopamine.[3][4] These are the neurotransmitters in charge of pleasure, motivation and focus. This is done by inhibiting the reuptake and reabsorption of the neurotransmitters after they have performed their function of transmitting a neural impulse, essentially allowing them to accumulate and be reused, causing physically stimulating and euphoric effects.

In comparison to MDMA, it has approximately 3x lower affinity for the serotonin transporter, 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 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.[8]

Subjective effects

The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.

Physical effects

  • Spontaneous tactile sensations - The "body high" of methylone can be described as a moderate to extreme euphoric tingling sensation that encompasses the entire body. It is capable of becoming overwhelmingly pleasurable at higher doses. This sensation maintains a consistent presence that steadily rises with the onset and hits its limit once the peak has been reached.
  • Stimulation - In terms of its effects on the user's physical energy levels, methylone is commonly considered to be extremely stimulating and energetic. This encourages activities such as running, climbing and dancing in a way that makes methylone a popular choice for musical events such as festivals and raves. The particular style of stimulation which methylone presents can be described as forced. This means that at higher doses, it becomes difficult or impossible to keep still as jaw clenching, involuntarily bodily shakes, and vibrations become present, resulting in an extreme unsteadiness of the hands and a general lack of motor control.
  • Vibrating vision - At high doses, a person's eyeballs may begin to spontaneously wiggle back and forth in a rapid motion, causing the vision to become blurry and temporarily out of focus. This is a condition known as nystagmus.
  • Dehydration - Feelings of dry mouth and dehydration are a universal experience with methylone; this effect is a product of an increased heart rate and an extreme motivation to engage in strenuous physical activities. While it is important to avoid becoming dehydrated (especially when out dancing in a hot environment) there have been a number of users suffering from water intoxication through over-drinking, so it is advised that users simply sip at water and never over-drink.
  • Difficulty urinating - Higher doses of methylone result in an overall difficulty when it comes to urination. This is an effect that is completely temporary and harmless. It is due to methylone’s promotion of the release of anti-diuretic hormone (ADH). ADH is responsible for regulating urination. This effect can be lessened by simply relaxing, but can be significantly relieved by placing a hot flannel over the genitals to warm them up and encourage blood flow.
  • Temperature regulation suppression
  • Tactile enhancement
  • Increased heart rate
  • Increased perspiration
  • Increased blood pressure
  • Teeth grinding - This component can be considered to be less intense when compared with that of MDMA.

Cognitive effects

The cognitive effects of methylone can be broken down into several components which progressively intensify proportional to dosage. The general head space of methylone is described by many as one of extreme mental stimulation, feelings of love or empathy and powerful euphoria. It contains a large number of typical psychedelic, entactogenic and stimulant cognitive effects.

The most prominent of these cognitive effects generally include:

  • Cognitive euphoria - Strong emotional euphoria and feelings of happiness are present within methylone and are likely a direct result of serotonin and dopamine release. In comparison to MDMA, it is closer in effects to that of the euphoria felt within amphetamine and mephedrone.
  • Empathy, love and sociability enhancement - Although distinct and powerful in its effects, this particular feeling is less pronounced and therapeutic when compared to that of MDMA. It can be described as less forceful and more internal in its manifestation, resulting in feelings of love and empathy that are not necessarily felt as essential to express to others.
  • Time distortion - Strong feelings of time compression are common within methylone and speed up the experience of time quite noticeably.
  • Thought acceleration
  • Analysis enhancement
  • Mindfulness
  • Increased libido

After effects

The effects which occur during the offset of a stimulant experience generally feel negative and uncomfortable in comparison to the effects which occurred during its peak. This is often referred to as a "comedown" and occurs because of neurotransmitter depletion. Its effects commonly include:

Toxicity and harm potential

Main article: Research chemicals § 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 very little history of human usage. Anecdotal evidence from people who have tried methylone within the community suggest that there do not seem to be any negative health effects attributed to simply trying this drug 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 drug.

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 3 - 7 days for the tolerance to be reduced to half and 1 - 2 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 drugs 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 issues

  • 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.[16]
  • 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.
  • United Kingdom: In the U.K., methylone has been illegal since the 16/04/2010 revision of the Misuse of Drugs Act.
  • Sweden: Methylone has been listed as a Schedule I narcotic in Sweden as of Oct 1 of 2010.[17]
  • Canada: Although not listed as a Schedule 1[18] 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.[19]
  • United States: As of October 21, 2011, the DEA has issued an emergency ban on methylone. It is illegal to possess and distribute.[20][21]
  • Germany: On July 26, 2012, methylone was added to Germany's controlled substance act ("BtMG"), making it illegal to produce, sell or possess.[22]

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.

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. ↑ Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity | http://bja.oxfordjournals.org/content/95/4/434
  16. ↑ van Amsterdam et al., 2004
  17. ↑ http://www.lakemedelsverket.se/upload/lvfs/LVFS_2010_23.pdf
  18. ↑ http://isomerdesign.com/Cdsa/schedule.php?schedule=1&section=18.5&structure=C
  19. ↑ http://isomerdesign.com/Cdsa/definitions.php?structure=C
  20. ↑ "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
  21. ↑ "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
  22. ↑ 26. BtMÄndVO in Kraft getreten | http://www.buzer.de/gesetz/10254/index.htm
Last modified on 13 June 2016, at 14:27