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Description

Ethylone Also known as:

  • 1-(1,3-Benzodioxol-5-yl)-2-(ethylamino)-1-propanon[German][ACD/IUPAC Name]
  • 1-(1,3-Benzodioxol-5-yl)-2-(ethylamino)-1-propanone[ACD/IUPAC Name]
  • 1-(1,3-Benzodioxol-5-yl)-2-(éthylamino)-1-propanone[French][ACD/IUPAC Name]
  • 1-Propanone, 1-(1,3-benzodioxol-5-yl)-2-(ethylamino)-[ACD/Index Name]
  • 3,4-Methylenedioxy-N-ethylcathinone
  • bk-MDEA
  • L91C78FW96
  • MDEC
  • UNII:L91C78FW96
  • 1-(1,3-benzodioxol-5-yl)-2-(ethylamine) propane-1-one[ACD/IUPAC Name]
  • 1-(1,3-benzodioxol-5-yl)-2-(ethylamino)propan-1-one
  • 1-(1,3-benzodioxol-5-yl)-2-ethylaminopropan-1-one
  • 2-ETHYLAMINO-1-(3,4-METHYLENEDIOXYPHENYL)PROPAN-1-ONE

A euphoric stimulant often sold in place of MDMA since methylone was banned. Slightly less potent and empathogenic than methylone, it is often described as more of a ‘straight stimulant.’

Summary

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 (all of which have collectively come to be referred to as "Molly") 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.

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

Ethylone

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.

Common NameEthylone
Systematic nameEthylone
FormulaC_{12}H_{15}NO_{3}
SMILESCCNC(C)C(=O)c1ccc2c(c1)OCO2
Std. InChiInChI=1S/C12H15NO3/c1-3-13-8(2)12(14)9-4-5-10-11(6-9)16-7-15-10/h4-6,8,13H,3,7H2,1-2H3
Std. InChiKeyMJEMIOXXNCZZFK-UHFFFAOYSA-N
Avg. Mass221.2524 Da
Molecular Weight221.2524
Monoisotopic Mass221.105194 Da
Nominal Mass221
ChemSpider ID21106271

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Dose Chart

Oral
Light125-175mg
Common200-250mg
Strong250-400mg

Duration Chart

Ethylone Duration Data
Onset30-45 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

Psychological Effects

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:

Pharmacological Effects

Ethylone acts as a mixed reuptake inhibitor/releasing agent of serotonin, norepinephrine, and dopamine. 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. 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.

Physical Effects

  • 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.

Subjective Effects

Disclaimer: The effects listed below are cited from the Subjective Effect Index (SEI), which relies on assorted anecdotal reports and the personal experiences of PsychonautWiki contributors. As a result, they should be taken with a healthy amount of skepticism. It is worth noting that these effects will not necessarily occur in a consistent or reliable manner, although higher doses (common+) are more likely to induce the full spectrum of reported effects. Likewise, adverse effects become much more likely on higher doses and may include serious injury or death.

Legal Status

  • Brazil: Ethylone is illegal to possess, produce, and sell under Portaria SVS/MS nº 344.
  • China: As of October 2015, Ethylone is a controlled substance in China.
  • Germany: Ethylone is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of December 13, 2014. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.
  • United Kingdom: Ethylone is a Class B drug in the United Kingdom as a result of the cathinone catch-all clause.
  • 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.
  • Sources

    References

    1. "Cathinone | Ask Dr. Shulgin Online".
    2. Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/10528135
    3. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299906013811
    4. "Pharmacological characterization of designer cathinones in vitro" | http://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.2012.02145.x/pdf
    5. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299906013811
    6. "Pharmacological characterization of designer cathinones in vitro" | http://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.2012.02145.x/pdf
    7. Treatment for amphetamine psychosis | [1]
    8. Treatment for amphetamine psychosis | [2]
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    10. Treatment for amphetamine psychosis | [3]
    11. Stimulant Misuse: Strategies to Manage a Growing Problem | http://www.acha.org/prof_dev/ADHD_docs/ADHD_PDprogram_Article2.pdf
    12. http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021303s026lbl.pdf
    13. 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
    14. 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
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    16. "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.
    17. "Anlage I BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 25, 2019.
    18. "Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (PDF) (in German). Bundesanzeiger Verlag. Retrieved December 25, 2019.
    19. "§ 29 BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 25, 2019.
    20. 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

    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.