Ethylone
| Summary sheet: Ethylone |
| Ethylone | |||||||||||||||||||||||||||||||
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| Chemical Nomenclature | |||||||||||||||||||||||||||||||
| Common names | Ethylone, bk-MDEA, MDEC | ||||||||||||||||||||||||||||||
| Substitutive name | 3,4-methylenedioxy-N-ethylcathinone | ||||||||||||||||||||||||||||||
| Systematic name | (RS)-1-(1,3-benzodioxol-5-yl)-2-(ethylamino)propan-1-one | ||||||||||||||||||||||||||||||
| Class Membership | |||||||||||||||||||||||||||||||
| Psychoactive class | Stimulant / Entactogen | ||||||||||||||||||||||||||||||
| Chemical class | Cathinone / MDxx | ||||||||||||||||||||||||||||||
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3,4-methylenedioxy-N-ethylcathinone (also known as Ethylone, MDEC and βk-MDEA) is a synthetic entactogen and stimulant of the cathinone class. It is the β-keto analog of MDEA ("Eve").
As a designer drug, ethylone is commonly sold on the street along with other cathinones like butylone or 3-MMC as a substitute or counterfeit for MDMA and/or methylone due to methylone's declining availability on the research chemicals market. However, in spite of behavioral and pharmacological similarities between ethylone, MDMA and methylone, it should be noted that the observed subjective effects of both drugs are not completely identical. [1]
Ethylone has only a short history of human use and is reported to be less potent than its relative methylone as well as possessing more classical stimulant-type as opposed to entactogenic effects.
Chemistry
Ethylone, or 3,4-methylenedioxy-N-ethylcathinone, is a synthetic molecule of the cathinone family. Cathinones are structurally similar to amphetamines in that 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 ethylone are alpha-methylated phenethylamines (i.e. amphetamines) but differ from them with the addition of a ketone functional group (a carbonyl group at Rβ). Ethylone contains an ethyl substitution at RN, a substitution which is shared with drugs like MDEA, 4-MEC, and certain other stimulants and entactogens. Additionally, ethylone contains 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. Ethylone shares this methylenedioxy ring with MDA, MDAI and MDMA.
Pharmacology
Ethylone acts as a mixed reuptake inhibitor/releasing agent of serotonin, norepinephrine, and dopamine.[2][3] These are the neurotransmitters in charge of pleasure, reward, 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 methylone, it has approximately over 3x lower affinity for the serotonin transporter (which itself has 3x lower affinity than MDMA), while its affinity for the norepinephrine and dopamine transporters is similar.[4][3] The results of these differences in pharmacology relative to methylone is that ethylone 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, ethylone still has relatively robust releasing capabilities.[4]
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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- Spontaneous physical sensations - The "body high" of ethylone 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, ethylone is commonly considered to be extremely stimulating and energetic. This encourages activities such as running, climbing and dancing in a way that makes ethylone a popular choice for musical events such as festivals and raves. The particular style of stimulation which ethylone 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 ethylone; 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 ethylone result in an overall difficulty when it comes to urination. This is an effect that is completely temporary and harmless. It is due to ethylone’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 
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The cognitive effects of ethylone can be broken down into several components which progressively intensify proportional to dosage. The general head space of ethylone is described by many as one of extreme mental stimulation, light feelings of love or empathy and moderate 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 ethylone 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 ethylone and speed up the experience of time quite noticeably.
- Thought acceleration
- Analysis enhancement
- Mindfulness
- Increased libido
- Increased music appreciation
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 ethylone 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 ethylone 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 substance.
Dependence and abuse potential
As with other stimulants, the chronic use of ethylone 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 ethylone 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). Ethylone presents cross-tolerance with all dopaminergic stimulants, meaning that after the consumption of ethylone 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
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.
- Stimulants - Ethylone can be potentially dangerous in combination with other stimulants as it can increase one's heart rate and blood pressure to dangerous levels.
- 25x-NBOMe & 25x-NBOH - 25x compounds are highly stimulating and physically straining. Combinations with Ethylone 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 - Ethylone 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.
- Cocaine - This combination may increase strain on the heart.
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
- Brazil: Ethylone is illegal to possess, produce, and sell under Portaria SVS/MS nº 344.[10]
- China: As of October 2015, Ethylone is a controlled substance in China.[11]
- Germany: Ethylone is controlled under Anlage I BtMG (Narcotics Act, Schedule I)[12] as of December 13, 2014.[13] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[14]
- Sweden: Ethylone is a controlled substance since 1992[15]
- Switzerland: Ethylone is a controlled substance specifically named under Verzeichnis D.[16]
- United Kingdom: Ethylone is a Class B drug in the United Kingdom as a result of the cathinone catch-all clause.[17]
- United States: Ethylone is unscheduled in the United States. However it could be considered an analog of methylone or MDMA, thus putting it under the scope of the Federal Analog Act.[citation needed]
See also
External links
Discussion
References
- ↑ "Cathinone | Ask Dr. Shulgin Online".
- ↑ 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.
- ↑ 3.0 3.1 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.
- ↑ 4.0 4.1 Simmler, L., Buser, T., Donzelli, M., Schramm, Y., Dieu, L.-H., Huwyler, J., Chaboz, S., Hoener, M., Liechti, M. (January 2013). "Pharmacological characterization of designer cathinones in vitro: Pharmacology of cathinones". British Journal of Pharmacology. 168 (2): 458–470. doi:10.1111/j.1476-5381.2012.02145.x. ISSN 0007-1188.
- ↑ 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.
- ↑ http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
- ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.
- ↑ "Anlage I BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 25, 2019.
- ↑ "Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (PDF) (in German). Bundesanzeiger Verlag. Retrieved December 25, 2019.
- ↑ "§ 29 BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 25, 2019.
- ↑ http://rkrattsbaser.gov.se/sfst?fritext=etylon&upph=false&sort=desc
- ↑ "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