Abstract

Eutylone (also recognized as β-keto-1,3-benzodioxolyl-N-ethylbutanamine, bk-EBDB, and N-ethylbutylone) is a stimulant and empathogenic substance created in the 1960s, categorized as a designer drug. It was initially documented by the EMCDDA in 2014 and gained global prevalence between 2019 and 2020, following prohibitions on the related compound ephylone. Eutylone is not a naturally occurring substance but rather a synthetic cathinone. In 2021, it stood out as the most frequently identified cathinone by the Drug Enforcement Administration in the United States. This article provides overview of eutylone, general information, physico-chemical properties, recreational pharmacology, effects and symptoms, street names, prices and approximate dosages, legal status, eutylone synthesis, conclusion, and bibliography.

Medical experts concerned over surge in overdoses, deaths from eutylone — aka ‘bath salts’ — i…

General information About Eutylone

Other synonyms names of Eutylone are: 1-(1,3-Benzodioxol-5-yl)-2-(ethylamino)-1-butanon; DL-eutylone; 1-(1,3-benzodioxol-5-yl)-2-(ethylamine)buthane-1-one; 1-(2H-1,3-Benzodioxol-5-yl)-2-(ethylamino)butan-1-one; 2-Ethyl-5-methyl-2H-pyrazol-3-ylamine; 1-(1,3-Benzodioxol-5-yl)-2-(ethylamino)-1-butanone; N-Ethylbutylone; BKMDMA CRYSTAL; bk-EBDB; keto-Ethylbenzodioxolylbutanamine

IUPAC Name of Eutylone: 1-(1,3-benzodioxol-5-yl)-2-(ethylamino)butan-1-one

CAS numbers are 802855-66-9 (free base); 17764-18-0 (hydrochloric salt)

Physico-Chemical Properties of Eutylone

• Molecular formula: C₁₃H₁₇NO₃
• Molar Weight: 235.28 g/mol
• Boiling Point: 374.7±42.0 °C
• Melting point: 238–239°C (hydrochloride salt)
• Solubility: The hydrochloride salt is soluble in water, methanol, ethanol, DMF and DMSO
• Color/Form: The drug’s hydrochloride salt has been characterized as a crystalline solid.
• Odor: There are currently no documented observations regarding its odor; however, its molecular structure suggests that its pure state is anticipated to lack any discernible scent.

Structural formula present on Figure 1.

Powder and crystalline solid possible of the eutylone can be seen in the pictures provided in Figure 2 and Figure 3.

General Information of Eutylone in Recreational Use and Pharmacology:

Eutylone, also known as bk-EBDB or n-ethylbutylone, represents a stimulant within the synthetic cathinone family, categorized under the broader class of New Psychoactive Substances (NPS), often termed designer drugs, novel designer drugs, or bath salts. Exhibiting chemical and pharmacological resemblances to schedule I and II amphetamines and cathinones like 3,4-methylenedioxymethamphetamine (MDMA), methylone, and pentylone, eutylone is identified as a synthetic cathinone commonly abused for its psychoactive effects.

Functioning as a synthetic cathinone, eutylone exerts psychostimulant effects primarily through interactions with monoamine transporters in the brain. Studies indicate its inhibition of neurotransmitter uptake at dopamine and norepinephrine transporters, coupled with partial releasing actions at serotonin transporters. The robust locomotor activity observed in mice suggests potential abuse liability and psychostimulant side effects in humans. Despite gaining popularity as a recreational substance, eutylone is both illegal and strongly discouraged due to associated risks and adverse effects.

In clinical contexts, eutylone finds application in scientific research and forensic analysis, leveraging its psychoactive properties and detectability in biological samples. Its prevalence in forensic investigations, often linked to impairments and fatalities, underscores the necessity for controlled laboratory use and heightened awareness among law enforcement and medical professionals.

Eutylone, being a synthetic cathinone with psychostimulant effects, carries inherent risks such as hospitalizations, overdose, and even death. Structurally akin to methylone, another synthetic cathinone, eutylone’s pharmacological effects remain somewhat underexplored. In vitro transporter assays using rat brain synaptosomes and in vivo locomotor activity assessments in mice suggest its dose-dependent inhibition of neurotransmitter uptake at dopamine transporters (DAT) and norepinephrine transporters (NET), with stronger potency at DAT. Eutylone and pentylone also exhibited inhibitory effects at serotonin transporters (SERT), whereas dibutylone did not. Additionally, eutylone and pentylone displayed weak partial releasing actions at SERT, contributing to their psychostimulant effects. These findings highlight eutylone’s multifaceted interaction with various transporters, implying abuse liability and potential psychostimulant side effects in human users, reminiscent of its structural analog, pentylone.

Effects and symptoms of Eutylone use [7]

Considering the molecular structure of eutylone, it is anticipated that the substance will induce stimulant-related psychological and somatic effects akin to schedule I synthetic cathinones (such as methylone and pentylone) and schedule I and II substances like cocaine, methamphetamine, and MDMA. Adverse effects linked to the abuse of synthetic cathinones encompass agitation, hypertension, tachycardia, and, in severe cases, fatalities.

Online discussions in chat rooms have highlighted users’ experiences with eutylone for recreational purposes, emphasizing positive effects. Users reported sensations of euphoria, insomnia, anxiety, tachycardia, hypertension, hyperthermia, delirium, paranoia, visual hallucinations, rhabdomyolysis, social disinhibition, warm tingling sensations, nausea, vomiting, and, in extreme instances, seizures and death. Unverified online accounts have also mentioned bruxism and irritation of mucous membranes following nasal administration.

Street names, Prices and Approximate Dosage

Street Aliases: Eutylone, bk-EBDB, MDEBP, β-Keto-ethylbenzodioxolylbutanamine, NEthylbutylone. In the year 2021 in New Zealand, eutylone was identified in tablets labeled as “Red Bull” and “Blue Playboys” (KnowYourStuffNZ, 2021). The presence of eutylone has also been confirmed in substances suspected to be “Ecstasy,” “Molly,” or 3,4-methylenedioxymethamphetamine (“MDMA”) (Krotulski et al., 2020). Seizure reports indicate that eutylone is commonly distributed in various forms, including tablets, capsules, crystals, and pills, suggesting that oral ingestion is the primary intended method of administration. However, there are also reports of nasal administration in online user forums. Eutylone has been identified in tablets of different colors, such as pink, yellow, and blue.

Prices: $600 per 100 g; $1900 per 1000 g.

Some users have reported experiencing effects at a dosage as low as 35 mg, with an average reported dose ranging from 60 to 100 mg. However, eutylone has been detected in “Red Bull” tablets (without MDMA) at doses as high as 300-350 mg (KnowYourStuffNZ, 2021). Information shared in online user forums suggests snorting 50 mg of eutylone (“Nick”, 2021), or oral administration ranging from 100-200 mg (“Ekstasis-//7”, 2020; “Nick”, 2021).

Legal Status

Brazil (BR): Designated as Class F2 (Restricted Psychotropics)

Canada (CA): Classified under Schedule I

Germany (DE): Listed in Anlage II (Authorized for trade only, non-prescriptible)

United Kingdom (UK): Categorized as Class B

United States (US): Enlisted in Schedule I

United Nations (UN): Recognized under Psychotropic Schedule II

Synthesis of Eutylone [14]

The first synthesis of eutylone was described in a 1960’s patent by a German pharmaceutical company (Glatfelter et al., 2021, C.H. Boehringer Sohn AG & Co. KG, 1967). However, the chemical synthesis of cathinones is facile and usually follows a two-step process. The initial synthesis is of an α-bromoketone from the appropriate arylketone, followed by a nucleophilic substitution with an appropriate amine to give the corresponding freebase of the cathinone. The cathinones are generally isolated as their salts due to the instability of the freebase. In the case of eutylone (Figure 4), the procedure includes the α- bromination of the 1-(2H-1,3-benzodioxol-5-yl)butan-1-one precursor and formation of the 1-(2H-1,3-benzodioxol-5-yl)-2-bromobutan-1-one intermediate. Reaction with N-ethylamine gives eutylone, which may then be converted into its hydrochloride salt. This procedure has been also employed for the preparation of eutylone analogs.

Conclusion

Eutylone, a synthetic cathinone, shares structural and pharmacological similarities with known stimulants, suggesting potential risks and adverse effects similar to substances like methylone and pentylone. The reported adverse effects, ranging from euphoria to insomnia and hallucinations, indicate a complex and varied response to the drug.

Its prevalence in differently colored tablets and various forms for recreational distribution underscores its diversity in the illicit market. The variable administration routes, including nasal use, may contribute to differences in reported effects and health risks.

Legal classifications vary across jurisdictions, with eutylone being recognized under different schedules and classes, reflecting the global effort to regulate its use. The pricing information reveals its economic accessibility, while reported dosages show a wide range, highlighting the need for caution and informed decision-making among potential users.

Bibliography

1. https://en.wikipedia.org/wiki/Eutylone
2. https://pubchem.ncbi.nlm.nih.gov/compound/57360686
3. https://www.chemspider.com/Chemical-Structure.26716427.html
4. https://www.chemicalbook.com/article/eutylone-mechanism-of-action-clinical-applications-and-toxicity.htm
5. https://www.chemicalbook.com/article/the-negative-impact-of-eutylone-hydrochloride-for-human.htm
6. https://commonchemistry.cas.org/detail?cas_rn=802855-66-9
7. https://adf.org.au/drug-facts/ethylone/
8. https://www.biosynth.com/p/CHB85566/802855-66-9-eutylone
9. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB44672577.htm
10. “WHO Expert Committee on Drug Dependence. Forty-fourth report” World Health Organization (2022)
11. “A fatal case of intoxication from a single use of eutylone: Clinical symptoms and quantitative analysis results”. Mami Nakamura, Marin Takaso, Arisa Takeda, Masahito Hitosugi (2022) https://doi.org/10.1016/j.legalmed.2022.102085
12. “Eutylone and Its Structural Isomers Interact with Monoamine Transporters and Induce Locomotor Stimulation”, Grant C. Glatfelter, Donna Walther, Michael Evans-Brown, and Michael H. Baumann (ACS Chem. Neurosci. 2021, 12, 1170−1177)
13. https://healthyliferecovery.com/what-is-eutylone/
14. Critical Review Report: EUTYLONE. Expert Committee on Drug Dependence Forty-fourth Meeting Geneva, 11-15 October 2021. World Health Organization. Unedited-Advance copy 44th ECDD (2021): Eutylone. https://cdn.who.int/media/docs/default-source/essential-medicines/unedited-advance-copy-44th-ecdd-critical-review-report-eutylone.pdf?sfvrsn=ca370181_3&download=true