Talk:Eutylone: Difference between revisions

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'''Eutylone''' '''β-''Keto-1,3-''benzodioxolyl-''N-''ethylbutanamine''' ('''Eutylone''', '''bk-EBDB''', '''N-Ethylbutylone'') is a stimulant compound developed in the 1960s which has been reported as a novel designer drug and has appeared recently (2019) being sold as a designer drug.
'''Eutylone''' (also known as '''β-keto-1,3-benzodioxolyl-''N''-ethylbutanamine''', '''bk-EBDB''', '''''N''-Ethylbutylone''', or '''euty''') is a [[psychoactive class::stimulant]] which has been reported as a novel designer drug and has appeared in 2019 being sold as a designer drug.
As a [[designer drug]], it is commonly sold on the street along with [[ethylone]] as a substitute or counterfeit for [[NEP]] and [[methylone]] (all of which have collectively come to be referred to as "stimulating with low serotonergic activity") due to methylone's declining availability on the [[research chemical]] market. However, in spite of behavioral and pharmacological similarities between eutylone and MDMA, the observed subjective effects of both substances are not completely identical, eutylone has some of the euphoria which can remind of that of MDMA, but with a shorter duration and weaker effects. . <ref name="urlCathinone | Ask Dr. Shulgin Online">{{cite web | url = http://www.cognitiveliberty.org/shulgin/adsarchive/cathinone.htm | title = Cathinone &#124; Ask Dr. Shulgin Online }}</ref>
As a [[designer drug]], it is commonly sold among [[research chemical]] vendors as a substitute for, or counterfeit of [[MDMA]] and [[methylone]], due to methylone's declining availability on the [[research chemical]] market. Despite behavioral and pharmacological similarities between eutylone and MDMA, the reported subjective effects of the two are not completely identical. Eutylone's effects are often described as being reminiscent of MDMA, but with a shorter duration and weaker effects.<ref name="urlCathinone | Ask Dr. Shulgin Online">{{cite web | url = http://www.cognitiveliberty.org/shulgin/adsarchive/cathinone.htm | title = Cathinone &#124; Ask Dr. Shulgin Online }}</ref>


Subjective effects include [[stimulation]], [[thought acceleration]], [[motivation enhancement]], [[increased libido]], [[appetite suppression]] [[dehydration]], [[dry mouth]] , and [[euphoria]], Euthylone is reported to be less potent than its relatives [[butylone]], [[methylone]] and [[ethylone]] as well as possessing more classic [[stimulant]] as opposed to entactogenic effects.
Subjective effects include [[stimulation]], [[thought acceleration]], [[motivation enhancement]], [[increased libido]], [[appetite suppression]] [[dehydration]], [[dry mouth]] , and [[euphoria]], Euthylone is reported to be less potent than its relatives [[butylone]], [[methylone]] and [[ethylone]] as well as possessing more classic [[stimulant]] as opposed to entactogenic effects.


Euthylone has an extremely short history of human use and very little data exists about its pharmacological properties, metabolism, and toxicity. It is highly advised to use [[harm reduction practices]] if using this substance.
Euthylone has a short history of human use and very little data exists about its pharmacological properties, metabolism, and toxicity. It is highly advised to use [[harm reduction practices]] if using this substance.


==Chemistry==
==Chemistry==
Eutylone or '''β-''Keto-1,3-''benzodioxolyl-''N-''ethylbutanamine''' , is a synthetic molecule of the [[Substituted cathinone|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 ethyl substitution at R<sub>α</sub>. Cathinones such as eutylone are alpha-methylated phenethylamines (i.e. [[amphetamine]]s) but differ from them with the addition of a ketone functional group (a carbonyl group at R<sub>β</sub>).  
Eutylone is a synthetic substance of the [[Substituted cathinone|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 ethyl substitution at R{{Sub|α}}. Cathinones such as eutylone are alpha-methylated phenethylamines (i.e. [[amphetamine]]s) but differ from them with the addition of a ketone functional group (a carbonyl group at R<sub>β</sub>).  


==Pharmacology==
==Pharmacology==
Eutylone acts as a mixed [[reuptake inhibitor]]/[[releasing agent]] of [[serotonin]], [[norepinephrine]], and [[dopamine]].<ref>Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/10528135</ref><ref>The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299906013811</ref> 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.  
Eutylone acts as a mixed [[reuptake inhibitor]] and [[releasing agent]] of [[serotonin]], [[norepinephrine]], and [[dopamine]].<ref>Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/10528135</ref><ref>The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299906013811</ref> Eutylone modulates these[[neurotransmitters]] in charge of pleasure, reward, motivation and focus. This is done by inhibiting the reuptake and reabsorption of the neurotransmitters back into the cell 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 much lower affinity for the norepinephrine transporter, while its affinity for the serotonin and dopamine transporters is similar.<ref>"Pharmacological characterization of designer cathinones in vitro" | http://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.2012.02145.x/pdf</ref><ref>The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299906013811</ref> The results of these differences in pharmacology relative to [[MDMA]] is that butylone, like its close analog [[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, eutyulonestill has relatively robust releasing capabilities.<ref>"Pharmacological characterization of designer cathinones in vitro" | http://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.2012.02145.x/pdf</ref>
In comparison to [[methylone]], it has much lower affinity for the norepinephrine transporter, while its affinity for the serotonin and dopamine transporters is similar.<ref>"Pharmacological characterization of designer cathinones in vitro" | http://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.2012.02145.x/pdf</ref><ref>The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299906013811</ref> Despite this lower affinity, eutylone is a stronger [[reuptake inhibitor]] than [[MDMA]], although it is less potent and has a more balanced [[catecholaminergic]] profile. As a mixed releaser and reuptake inhibitor, it also has relatively robust releasing capabilities.<ref>"Pharmacological characterization of designer cathinones in vitro" | http://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.2012.02145.x/pdf</ref>


==Subjective effects==
==Subjective effects==
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|{{effects/physical|
|{{effects/physical|
*'''[[Effect::Stimulation]]''' - In terms of its effects on the user's physical energy levels, eutyulone is commonly considered to be highly stimulating and energetic. This encourages activities such as running, climbing and dancing in a way that makes eutyulone a popular choice for musical events such as festivals and raves. The particular style of stimulation which eutyulone 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.  
*'''[[Effect::Stimulation]]''' - In terms of its effects on the user's physical energy levels, eutylone is commonly considered to be highly stimulating and energetic. This encourages activities such as running, climbing and dancing in a way that makes eutylone a popular choice for musical events such as festivals and raves. The particular style of stimulation which eutylone 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.  
*'''[[Effect::Spontaneous physical sensations]]''' - The "body high" of eutyulone can be described as a strong 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.
*'''[[Effect::Spontaneous physical sensations]]''' - The "body high" of eutylone can be described as a strong 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.
*'''[[Effect::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 [http://en.wikipedia.org/wiki/Nystagmus nystagmus].
*'''[[Effect::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 [http://en.wikipedia.org/wiki/Nystagmus nystagmus].
*'''[[Effect::Dehydration]]''' - Feelings of dry mouth and dehydration are a universal experience with eutyulone ; 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 some users suffering from [[water intoxication]] through over-drinking, so it is advised that users simply sip at water and never over-drink.
*'''[[Effect::Dehydration]]''' - Feelings of dry mouth and dehydration are a universal experience with eutylone ; 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 some users suffering from [[water intoxication]] through over-drinking, so it is advised that users simply sip at water and never over-drink.
*'''[[Effect::Difficulty urinating]]''' - Higher doses of eutyulone result in an overall difficulty when it comes to urination. This is an effect that is entirely temporary and harmless. It is due to eutyulone'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.
*'''[[Effect::Difficulty urinating]]''' - Higher doses of eutylone result in an overall difficulty when it comes to urination. This is an effect that is entirely temporary and harmless. It is due to eutyulone'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.
*'''[[Effect::Temperature regulation suppression]]'''
*'''[[Effect::Temperature regulation suppression]]'''
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Tactile enhancement]]'''
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}}
}}
|{{effects/cognitive|
|{{effects/cognitive|
The cognitive effects of eutyulone can be broken down into several components which progressively intensify proportional to dosage. The general headspace of eutyulone 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 [[Psychedelics|psychedelic]], [[Entactogens|entactogenic]] and [[Stimulants|stimulant]] cognitive effects.  
The cognitive effects of eutylone can be broken down into several components which progressively intensify proportional to dosage. The general headspace of eutylone 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 [[Psychedelics|psychedelic]], [[Entactogens|entactogenic]] and [[Stimulants|stimulant]] cognitive effects.  


The most prominent of these cognitive effects include:
The most prominent of these cognitive effects include:


*'''[[Effect::Cognitive euphoria]]''' - Strong emotional euphoria and feelings of happiness are present within eutyulone 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]].
*'''[[Effect::Cognitive euphoria]]''' - Strong emotional euphoria and feelings of happiness are present within eutylone 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]].
*'''[[Effect::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.
*'''[[Effect::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.
*'''[[Effect::Time distortion]]''' - Strong feelings of time compression are common within eutyulone and speed up the experience of time quite noticeably.
*'''[[Effect::Time distortion]]''' - Strong feelings of time compression are common within eutylone and speed up the experience of time quite noticeably.
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Analysis enhancement]]'''
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As with other [[stimulant]]s, the chronic use of Eutylone can be considered [[Addiction potential::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.
As with other [[stimulant]]s, the chronic use of Eutylone can be considered [[Addiction potential::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 eutyulone [[Time to full tolerance::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 [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). Eutyulone presents cross-tolerance with [[Cross-tolerance::all [[dopamine]]rgic [[stimulant]]s]], meaning that after the consumption of Eutyulone all [[stimulant]]s will have a reduced effect.
Tolerance to many of the effects of eutylone [[Time to full tolerance::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 [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). Eutylone presents cross-tolerance with [[Cross-tolerance::all [[dopamine]]rgic [[stimulant]]s]], meaning that after the consumption of Eutylone all [[stimulant]]s will have a reduced effect.
===Psychosis===
===Psychosis===
{{Main|Stimulant psychosis}}
{{Main|Stimulant psychosis}}
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==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Entactogens]]
*[[Entactogens]]
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==External links==
==External links==
*[https://en.wikipedia.org/wiki/eutylone/Eutylone (Wikipedia)]
*[https://en.wikipedia.org/wiki/eutylone/Eutylone (Wikipedia)]
*[https://erowid.org/chemicals/eutylone/ Eutylone (Erowid Vault)]
*[https://erowid.org/chemicals/eutylone/ Eutylone (Erowid Vault)]
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[[Category:Stimulant]]
[[Category:Stimulant]]
[[Category:Entactogen]]
[[Category:Entactogen]]
[[Category:MDxx]]
[[Category:Cathinone]]
[[Category:Cathinone]]
[[Category:Research chemical]]
[[Category:Research chemical]]
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