Methylone
| Summary sheet: Methylone |
| Methylone | |||||||||||||||||||||||||||||||||
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| 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 / MDxx | ||||||||||||||||||||||||||||||||
| Routes of Administration | |||||||||||||||||||||||||||||||||
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| Interactions | |||||||||||||||||||||||||||||||||
| Alcohol | |||||||||||||||||||||||||||||||||
| MXE | |||||||||||||||||||||||||||||||||
| Dissociatives | |||||||||||||||||||||||||||||||||
| DXM | |||||||||||||||||||||||||||||||||
| MDMA | |||||||||||||||||||||||||||||||||
| Stimulants | |||||||||||||||||||||||||||||||||
| 25x-NBOMe | |||||||||||||||||||||||||||||||||
| 25x-NBOH | |||||||||||||||||||||||||||||||||
| Tramadol | |||||||||||||||||||||||||||||||||
| SNRIs | |||||||||||||||||||||||||||||||||
| MAOIs | |||||||||||||||||||||||||||||||||
| Serotonin releasers | |||||||||||||||||||||||||||||||||
| SSRIs | |||||||||||||||||||||||||||||||||
| 5-HTP | |||||||||||||||||||||||||||||||||
3,4-Methylenedioxy-N-methcathinone (also known as M1, MDMC, βk-MDMA, and Methylone) is a novel stimulant-entactogen substance of the cathinone class.
Methylone was first synthesized by chemists Peyton Jacob III and Alexander Shulgin in 1996 as a potential antidepressant.[1]
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."[2]
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, 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.[3][4] Notably, methylone's affinity for the vesicular monoamine transporter 2 (VMAT2) is about 13x lower than that of MDMA.[3]
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.[4]
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
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.
It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.
Physical effects 
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- 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.
- Spontaneous physical 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.
- Tactile enhancement
- Increased heart rate[citation needed]
- Increased perspiration
- Increased blood pressure[citation needed]
- Temperature regulation suppression[citation needed]
- 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 sip at water and avoid over-drinking.
- 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.
- 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.
- Teeth grinding - This component is reported to be less prominent in comparison to that of MDMA.
- Pupil dilation
Cognitive effects 
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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:
- Anxiety suppression
- Disinhibition
- 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, affection, 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.
- Psychosis
- Increased music appreciation
- Time compression - Strong feelings of time compression are common with methylone and speed up the experience of time quite noticeably. This can promote compulsive redosing.
- Compulsive redosing
- Thought acceleration
- Immersion enhancement
- Motivation enhancement
- Increased libido
- Wakefulness
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:
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
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This toxicity and harm potential section is a stub. As a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it. |
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.
Dependence and abuse 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
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).[5] A review on treatment for amphetamine, dextroamphetamine, and methamphetamine abuse-induced psychosis states that about 5–15% of users fail to recover completely.[5][6] The same review asserts that, based upon at least one trial, antipsychotic medications effectively resolve the symptoms of acute amphetamine psychosis.[5] Psychosis very rarely arises from therapeutic use.[7]
Dangerous interactions
Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).
Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.
- 25x-NBOMe & 25x-NBOH - 25x compounds are highly stimulating and physically straining. Combinations with Methylone should be strictly avoided due to the risk of excessive stimulation and heart strain. This can result in increased blood pressure, vasoconstriction, panic attacks, thought loops, seizures, and heart failure in extreme cases.
- Alcohol - Combining alcohol with stimulants can be dangerous due to the risk of accidental over-intoxication. Stimulants mask alcohol's depressant effects, which is what most people use to assess their degree of intoxication. Once the stimulant wears off, the depressant effects will be left unopposed, which can result in blackouts and severe respiratory depression. If mixing, the user should strictly limit themselves to only drinking a certain amount of alcohol per hour.
- DXM - Combinations with DXM should be avoided due to its inhibiting effects on serotonin and norepinephrine reuptake. There is an increased risk of panic attacks and hypertensive crisis, or serotonin syndrome with serotonin releasers (MDMA, methylone, mephedrone, etc.). Monitor blood pressure carefully and avoid strenuous physical activity.
- MDMA - Any neurotoxic effects of MDMA are likely to be increased when other stimulants are present. There is also a risk of excessive blood pressure and heart strain (cardiotoxicity).
- MXE - Some reports suggest combinations with MXE may dangerously increase blood pressure and increase the risk of mania and psychosis.
- Dissociatives - Both classes carry a risk of delusions, mania and psychosis, and these risk may be multiplied when combined.
- Stimulants - Methylone may be dangerous to combine with other stimulants like cocaine as they can increase one's heart rate and blood pressure to dangerous levels.
- Tramadol - Tramadol is known to lower the seizure threshold[8] and combinations with stimulants may further increase this risk.
Serotonin syndrome risk
Combinations with the following substances can cause dangerously high serotonin levels. Serotonin syndrome requires immediate medical attention and can be fatal if left untreated.
- MAOIs - Such as banisteriopsis caapi, syrian rue, phenelzine, selegiline, and moclobemide.[9]
- Serotonin releasers - Such as MDMA, 4-FA, methamphetamine, methylone and αMT.
- SSRIs - Such as citalopram and sertraline
- SNRIs - Such as tramadol and venlafaxine
- 5-HTP
Legal status
- Austria: Since June 26, 2019, methylone is illegal to possess, produce and sell under the SMG. (Suchtmittelgesetz Österreich)[10]
- Brazil: Methylone is illegal to possess, produce and sell as it is listed on Portaria SVS/MS nº 344.[11]
- Canada: Although not listed as a Schedule 1[12] 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.[13]
- Germany: Methylone is controlled under Anlage II BtMG (Narcotics Act, Schedule II)[14] as of July 26, 2012.[15] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[16]
- The Netherlands: Methylone is covered by the Medicine Act. Because methylone is not approved officially, it is forbidden to trade methylone.[17]
- 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]
- Russia: Methyloneis classed as a Schedule I prohibited substance.[18]
- Sweden: Methylone has been listed as a Schedule I narcotic in Sweden as of October 1, 2010.[19]
- Switzerland: Methylone is a controlled substance specifically named under Verzeichnis D.[20]
- United Kingdom: Methylone is a Class B drug in the United Kingdom as a result of the cathinone catch-all clause.[21]
- United States: As of October 21, 2011, the DEA has issued an emergency ban on methylone. It is illegal to possess and distribute.[22][23]
See also
External links
Discussion
References
- ↑ III, P. J., Shulgin, A. T., Novel n-substituted-2-amino-3’,4’-methylene-dioxypropiophenones
- ↑ "Cathinone | Ask Dr. Shulgin Online".
- ↑ 3.0 3.1 3.2 Cozzi, N. V., Sievert, M. K., Shulgin, A. T., Jacob, P., Ruoho, A. E. (17 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. ISSN 0014-2999.
- ↑ 4.0 4.1 4.2 Nagai, F., Nonaka, R., Satoh Hisashi Kamimura, K. (22 March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology. 559 (2): 132–137. doi:10.1016/j.ejphar.2006.11.075. ISSN 0014-2999.
- ↑ 5.0 5.1 5.2 Shoptaw, S. J., Kao, U., Ling, W. (21 January 2009). Cochrane Drugs and Alcohol Group, ed. "Treatment for amphetamine psychosis". Cochrane Database of Systematic Reviews. doi:10.1002/14651858.CD003026.pub3. ISSN 1465-1858.
- ↑ Hofmann, F. G. (1983). A handbook on drug and alcohol abuse: the biomedical aspects (2nd ed ed.). Oxford University Press. ISBN 9780195030563.
- ↑ http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021303s026lbl.pdf
- ↑ 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. doi:10.1007/BF03161089. eISSN 1937-6995. ISSN 1556-9039. OCLC 163567183.
- ↑ Gillman, P. K. (2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity". British Journal of Anaesthesia. 95 (4): 434–441. doi:10.1093/bja/aei210
. eISSN 1471-6771. ISSN 0007-0912. OCLC 01537271. PMID 16051647.
- ↑ https://www.ris.bka.gv.at/Dokumente/BgblAuth/BGBLA_2019_II_167/BGBLA_2019_II_167.pdfsig
- ↑ http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
- ↑ Controlled Drugs and Substances Act : Legislative history · Schedule I · Section 19: Tramadol [Proposed]; Amphetamines
- ↑ Controlled Drugs and Substances Act : Definitions and Interpretations
- ↑ "Anlage II BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 18, 2019.
- ↑ "Sechsundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (in German). Bundesanzeiger Verlag. Retrieved December 18, 2019.
- ↑ "§ 29 BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 18, 2019.
- ↑ van Amsterdam et al., 2004
- ↑ 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
- ↑ http://www.lakemedelsverket.se/upload/lvfs/LVFS_2010_23.pdf
- ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020.
- ↑ The Misuse of Drugs Act 1971 (Amendment) Order 2010
- ↑ "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
- ↑ "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