ETH-CAT: Difference between revisions

>Cannabis Entity
The warning for MAOIs was listed twice.
>Unity
Minor intro mods, chemistry and pharmacology section clean ups, cleaned up stim psychosis cites a bit, Legal issues -> Legality.
Line 2: Line 2:
{{SubstanceBox/ETH-CAT}}
{{SubstanceBox/ETH-CAT}}
{{SummarySheet}}
{{SummarySheet}}
'''Ethcathinone''' (also known as '''Ethylcathinone''', '''Ethylpropion''', and '''ETH-CAT''') is a synthetic [[psychoactive class::stimulant]] of the [[chemical class::cathinone]] chemical class that produces medium-lived typical [[amphetamine]] and [[cathinone]]-like [[stimulation]] when [[Routes of administration|administered]]. It is an active metabolite of the [[prodrug]] diethylcathinone and is thought to be responsible for its psychoactive effects.  
'''Ethylcathinone''' (also known as '''Ethylpropion''', '''Ethcathinone''', and commonly as '''ETH-CAT''') is a synthetic [[psychoactive class::stimulant]] of the [[chemical class::cathinone]] chemical class that produces an array of medium-lived [[cathinone]] or [[amphetamine]]-like [[stimulation]] when [[Routes of administration|administered]]. It is an active metabolite of the [[prodrug]] diethylcathinone and is thought to be responsible for its psychoactive effects.  


Of the simple substituted cathinones, ethcathinone has been reported to be one of the most moderate and residually enduring in its stimulation. Although it has no strong, habit-forming rush component like [[mephedrone]] ('''4-methylmethcathinone'''), ethcathinone is often reported to exhibit a tendency to induce compulsive redosing, albeit in a manner to extend the effects rather than reproduce the intial rush. It has a relatively short period of human use but is generally considered to be well tolerated due to the so-called "ceiling effect" it is commonly reported to display with reference to the amount of [[euphoria]] it can produce compared to many other [[cathinone]] and [[amphetamine]] derived stimulants substances.  
Of the [[substituted cathinones]], ETH-CAT has been reported to be one of the most moderate, subtle and residually enduring in its stimulation. Although it has no pronounced, habit-forming "rush" component like [[mephedrone]] ('''4-methylmethcathinone'''), ETH-CAT is often reported to exhibit a tendency to induce [[compulsive redosing]], albeit in a manner that is often intended to just extend the effects of the plateau rather than reproduce the initial rush. It has a relatively short period of human use but is generally suspected to be well tolerated and relatively safe, extrapolating from the molecular structure as well as reports of it exhibiting a so-called "ceiling effect" that generally limits the amount of potentially-distracting [[euphoria]] it can produce compared to many other stimulant substances in its family.  


Historically, ethcathinone has rarely been available on the streets, but was instead primarily distributed as a [[research chemical]] on the online grey market.<ref>Isomeric fluoro-methoxy-phenylalkylamines: a new series of controlled-substance analogues (designer drugs) (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/15639609</ref><ref>Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine, alpha-phthalimidopropiophenone and N-ethylcathinone (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/20074881</ref> However, in 2008 it was identified as an ingredient in both quasi-legal "party pills", and, along with another [[substituted cathinone]], [[mephedrone]], has also been reported as having been sold as "ecstasy"<ref>Police warn of potentially fatal 'fake ecstasy' | http://www.abc.net.au/news/2008-06-17/police-warn-of-potentially-fatal-fake-ecstasy/2475270</ref>
Historically, ETH-CAT has rarely been available on the streets, but was instead primarily distributed as a [[research chemical]] on the online grey market.<ref>Isomeric fluoro-methoxy-phenylalkylamines: a new series of controlled-substance analogues (designer drugs) (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/15639609</ref><ref>Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine, alpha-phthalimidopropiophenone and N-ethylcathinone (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/20074881</ref> However, in 2008 it was identified as an ingredient in both quasi-legal "party pills", and, along with another [[substituted cathinone]], [[mephedrone]], has also been reported as having been sold as "ecstasy"<ref>Police warn of potentially fatal 'fake ecstasy' | http://www.abc.net.au/news/2008-06-17/police-warn-of-potentially-fatal-fake-ecstasy/2475270</ref>


Due to its short history of human use, moderately compulsive nature, and unknown toxicity profile, it is strongly advised to use [[harm reduction]] techniques if choosing to use this substance.
Due to its short history of human use, moderately compulsive nature, and unknown toxicity profile, it is strongly advised to use [[harm reduction]] techniques if choosing to use this substance.


==Chemistry==
==Chemistry==
Ethcathinone, or ethylcathinone, is a synthetic [[alkaloid]] of the [[substituted cathinone]] class. Substituted cathinones derive from [[cathinone[[, the principal active psychoactive component in the [[khat]] plant. Cathinone is comprised of a [[phenethylamine]] core featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain containing a beta-ketone group. In distinction to its N-methylated lower homolog, methcathinone (M-CAT), ETH-CAT possesses an additional ethyl substitution at R<sub>α</sub>. ETH-CAT can be thought of as the cathinone analog of [[ethylamphetamine]] given it has the same general formula, differing only in the addition of a single double bonded oxygen.
Ethylcathinone, or ETH-CAT, is a synthetic [[alkaloid]] of the [[substituted cathinone]] class. Substituted cathinones are all derivatives of [[cathinone]], a stimulant substance which is structurally and functionally related to [[amphetamine]] and the principal active psychoactive component present in the [[khat]] plant (''Catha edulis''). The cathinone molecule is comprised of a [[phenethylamine]] core featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group at the end of an ethyl side-chain that contains ketone group in the beta position. In distinction to its N-methylated lower homolog, methcathinone (M-CAT), ETH-CAT possesses an additional ethyl substitution at R<sub>α</sub>. ETH-CAT can be thought of as the cathinone analog of [[ethylamphetamine]] given it has the same general formula, differing only by the addition of a single double-bonded oxygen (i.e. the ketone group).


[[File:Cathinone-general-structure.gif|thumbnail|right|215px|Cathinone substitutive structure.]]
[[File:Cathinone-general-structure.gif|thumbnail|right|215px|Cathinone substitutive structure.]]


==Pharmacology==
==Pharmacology==
Although the effects of ethcathinone have not been formally studied on the same level as traditional [[amphetamines]] or other substituted cathinones like [[methcathinone]], it is possible to speculate that like other simple [[substituted cathinone]], it most likely acts principally as a [[dopamine]] and [[norepinephrine]] [[reuptake inhibitor]].<ref>Cathinone derivatives: A review of their
Although the effects of ETH-CAT have not been formally studied on the same level as traditional [[amphetamines]] or other substituted cathinones like [[methcathinone]], it is possible to speculate that like other simple [[substituted cathinone]], it most likely acts principally as a [[dopamine]] and [[norepinephrine]] [[reuptake inhibitor]].<ref>Kelly, J. P. (2011). Cathinone derivatives: a review of their chemistry, pharmacology and toxicology. ''Drug Testing and Analysis'', 3(7‐8), 439-453. https://doi.org/10.1002/dta.31</ref>  
chemistry, pharmacology and toxicology | DOI 10.1002/dta.31</ref> The result of this is an effective increase in the levels of the norepinephrine and dopamine [[neurotransmitters]] in the brain by binding to and partially blocking the transporter proteins that normally clear those monoamines from the synaptic cleft. This allows dopamine and norepinephrine to accumulate within the key area of the brain linked to reward and pleasure to extra-endogenous levels, resulting in stimulating, motivatory and euphoric effects.
 
The result of this is an effective increase in the levels of [[catecholamine]] [[neurotransmitters]] like [[dopamine]] and [[norepinephrine]] in the brain by binding to and partially blocking the transporter proteins that normally clear these neurotransmitters from the synaptic cleft. This enables dopamine and norepinephrine to accumulate between the [[synaptic clef|synaptic clefs]] of key regions of the brain associated with reward, motivation, satisfaction and pleasure to extra-endogenous levels. This mechanism is thought to account for the [[Stimulation|stimulating]], [[Motivation enhancement|motivation enhancing]] and [[Euphoria|euphoric]] effects that this substance produces.


==Subjective effects==
==Subjective effects==
Ethylcathinone at low to moderate doses has been reported as being a relatively functional and effective amphetamine-like stimulant for performing general productivity tasks -- although its short duration of activity combined with its tendency to produce long-lasting residual stimulation may present a drawback compared to other stimulants due to the compulsive redosing it can induce to maintain a steady level of the desired amount of [[stimulation]]. However, at higher doses, it becomes less of a productivity-oriented stimulant and more of a recreational one, due to the distracting nature of the euphoria and stimulation it can produce. In this area however, it is reported as falling short of other, more potent related cathinone stimulants such as [[mephedrone]], [[methylone]], and [[methcathinone]].
At low to moderate doses, ETH-CAT has been reported as being a relatively functional and effective amphetamine-like stimulant for performing general productivity tasks. It has a noticeably short duration of activity combined with a tendency to produce long-lasting residual stimulation well after the main effects have worn off, which can promote patterns of [[compulsive redosing]] in order to maintain a steady level of the desired amount of physical and cognitive [[stimulation]]. However, at higher doses, it becomes less of a productivity-oriented stimulant and takes on a recreational character, perhaps owing to the inherently distracting nature of the type of [[thought acceleration]] and [[cognitive euphoria]] it can induce. However, even at high doses, it is reported as falling short of many other, far more hedonic and recreational [[substituted cathinones]] such as [[mephedrone]], [[methylone]], and [[methcathinone]] (M-CAT).


{{Preamble/SubjectiveEffects}}
{{Preamble/SubjectiveEffects}}
Line 33: Line 34:


===Cognitive effects===
===Cognitive effects===
The cognitive effects of ethcathinone can be broken down into several components which intensify proportional to dosage. The general head space of ethcathinone is described by many as one of mental stimulation coupled with mild euphoria, less present than that of [[amphetamine]], even at higher doses.
The cognitive effects of ETH-CAT can be broken down into several components which intensify proportional to dosage. The general head space of ETH-CAT is described by many as one of mental [[stimulation]] and [[thought acceleration]] coupled with a mild sense of euphoria that is less pronounced than the head space of [[amphetamine]], even at strong to heavy doses.


*'''[[Effect::Addiction suppression]]''' - In comparison to [[amphetamines]], ethylcathinone lacks pronounced euphoria, yet retains a similar effect profile, potentially offering reduced propensity to abuse.<ref>Therapeutic potential of monoamine transporter substrates. | https://www.ncbi.nlm.nih.gov/pubmed/17017961</ref> This does not, however, mean that ethylcathinone is absent from habit-forming effects on its own.
*'''[[Effect::Addiction suppression]]''' - In comparison to [[amphetamines]], ethylcathinone lacks pronounced euphoria, yet retains a similar effect profile, potentially offering reduced propensity to abuse.<ref>Therapeutic potential of monoamine transporter substrates. | https://www.ncbi.nlm.nih.gov/pubmed/17017961</ref> This does not, however, mean that ethylcathinone is absent from habit-forming effects on its own.
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Anxiety]]'''
*'''[[Effect::Anxiety]]''' - This compound produces little to no anxiety unless it is taken in large doses or redosed repeatedly.
*'''[[Effect::Cognitive euphoria]]'''
*'''[[Effect::Thought acceleration]]'''
**'''[[Effect::Cognitive euphoria]]'''
*'''[[Effect::Compulsive redosing]]'''  
*'''[[Effect::Compulsive redosing]]'''  
*'''[[Effect::Focus enhancement]]'''
*'''[[Effect::Focus enhancement]]'''
*'''[[Effect::Motivation enhancement]]'''
*'''[[Effect::Motivation enhancement]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought organization]]'''
*'''[[Effect::Thought organization]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Wakefulness]]'''
Line 71: Line 72:
==Toxicity and harm potential==
==Toxicity and harm potential==
{{Further|Research chemicals#Toxicity and harm potential}}
{{Further|Research chemicals#Toxicity and harm potential}}
The toxicity and long-term health effects of recreational ethcathinone use do not seem to have been studied in any scientific context and the [[Toxicity::exact toxic dosage is unknown]]. This is because ethcathinone has very little history of human usage. Anecdotal reports from people within the community who have tried ethcathinone 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). Others have commented that its d-isomer form is virtually similar to the effects of d-[[amphetamine]], and thus far little has been shown to give reason to suspect that its toxicity is radically different (though future evidence to the contrary may prove otherwise).  
The toxicity and long-term health effects of recreational ETH-CAT use do not seem to have been studied in any scientific context and the [[Toxicity::exact toxic dosage is unknown]]. This is because ETH-CAT has very little history of human usage. Anecdotal reports from people within the community who have tried ETH-CAT suggest that there do not seem to be any negative health effects attributed to simply trying this substance at low to moderate doses by itself and using it sparingly (although nothing can be completely guaranteed). Others have commented that its d-isomer form is virtually similar to the effects of [[amphetamine|d-isomer amphetamine]], and has thus far shown little reason to suspect that its toxicity is radically different (though this has yet to be scientifically validated).{{citation needed}}
 
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.


It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
===Tolerance and addiction potential===
===Tolerance and addiction potential===
As with other [[stimulants]], ETH-CAT may also possess habit-forming or reinforcing properties. Compared with other stimulants, however, chronic use of ETH-CAT is more likely to be considered to be only [[Addiction potential::mildly addictive with a comparatively low potential for abuse]]. Early studies demonstrate ETH-CAT suppresses cocaine self-administration in rhesus monkeys, without the adverse effects associated with older dopamine [[releasers|releasing agent]] (e.g., amphetamine).{{citation needed}} Despite this, ethcathinone may still be capable of causing psychological dependence among certain users.


As with other [[stimulant]]s, ethcathinone may also possess habit-forming or reinforcing properties. Compared with other stimulants, however chronic use of ethcathinone can be considered only [[Addiction potential::mildly addictive with a comparatively low potential for abuse]]. Early studies demonstrate ethcathinone suppresses cocaine self-administration in rhesus monkeys, without the adverse effects associated with older DA releasers (e.g., amphetamine).{{citation needed}} Despite this, ethcathinone may still be capable of causing psychological dependence among certain users.
Tolerance to many of the effects of ETH-CAT [[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::2 - 3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::3-5 days]] to be back at baseline (in the absence of further consumption). ETH-CAT presents cross-tolerance with [[Cross-tolerance::all [[dopamine]]rgic [[stimulant]]s]], meaning that after the consumption of ETH-CAT all [[stimulants]] will have a reduced effect.
 
Tolerance to many of the effects of ethyathinone [[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::2 - 3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::5-7 days]] to be back at baseline (in the absence of further consumption). Ethylcathinone presents cross-tolerance with [[Cross-tolerance::all [[dopamine]]rgic [[stimulant]]s]], meaning that after the consumption of ethcathinone all [[stimulant]]s will have a reduced effect.


===Psychosis===
===Psychosis===
{{Main|Stimulant psychosis}}
{{Main|Stimulant psychosis}}
Abuse of compounds within the amphetamine chemical 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|paranoia]], [[External hallucinations|hallucinations]], or [[Delusions|delusions]]).<ref>Treatment for amphetamine psychosis | [http://onlinelibrary.wiley.com/doi/10.1002/14651858.CD003026.pub3/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+Saturday%2C+15+March+from+10%3A00-12%3A00+GMT+%2806%3A00-08%3A00+EDT%29+for+essential+maintenance]</ref> A review on treatment for amphetamine, dextro[[amphetamine]], and [[methamphetamine]] abuse-induced psychosis states that about 5–15% of users fail to recover completely.<ref>Treatment for amphetamine psychosis | [http://onlinelibrary.wiley.com/doi/10.1002/14651858.CD003026.pub3/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+Saturday%2C+15+March+from+10%3A00-12%3A00+GMT+%2806%3A00-08%3A00+EDT%29+for+essential+maintenance]</ref><ref>Hofmann FG (1983). A Handbook on Drug and Alcohol Abuse: The Biomedical Aspects (2nd ed.). New York: Oxford University Press. p. 329. ISBN 9780195030570.</ref> The same review asserts that, based upon at least one trial, [[antipsychotic]] medications effectively resolve the symptoms of acute amphetamine psychosis.<ref>Treatment for amphetamine psychosis | [http://onlinelibrary.wiley.com/doi/10.1002/14651858.CD003026.pub3/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+Saturday%2C+15+March+from+10%3A00-12%3A00+GMT+%2806%3A00-08%3A00+EDT%29+for+essential+maintenance]</ref> Psychosis very rarely arises from therapeutic use.<ref>Stimulant Misuse: Strategies to Manage a Growing Problem | http://www.acha.org/prof_dev/ADHD_docs/ADHD_PDprogram_Article2.pdf</ref><ref>http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021303s026lbl.pdf</ref>
Abuse of compounds within the amphetamine chemical 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]], [[External hallucinations|hallucinations]], or [[delusions]]).<ref name="amptreat">Shoptaw SJ, Kao U, Ling W. Treatment for amphetamine psychosis. Cochrane Database of Systematic Reviews'', 1. https://doi.org/10.1002/14651858.CD003026.pub3 </ref> A review on treatment for [[amphetamine]] and [[methamphetamine]] abuse-induced psychosis states that about 5–15% of users fail to recover completely.<ref name="amptreat"><ref>Hofmann, F. G. (1983). A handbook on drug and alcohol abuse: the biomedical aspects. Oxford University Press. ISBN 9780195030570.</ref> The same review asserts that, based upon at least one trial, [[antipsychotic]] medications effectively resolve the symptoms of acute amphetamine psychosis.<ref name="amptreat" /> Psychosis is known to arises only very rarely from therapeutic use.<ref>Stimulant Misuse: Strategies to Manage a Growing Problem | http://www.acha.org/prof_dev/ADHD_docs/ADHD_PDprogram_Article2.pdf</ref><ref>http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021303s026lbl.pdf</ref>


==Legal issues==
==Legality==
Ethylcathinone is currently an unscheduled compound within all parts of the world, meaning its regulation lies in a legal grey area and is not explicitly prohibited within any country. However, people may still be charged for its possession under certain circumstances such as under analogue laws due to its similarity to methcathinone -- a widely prohibited substance -- and with intent to sell or consume.
ETH-CAT is currently an unscheduled compound within all parts of the world, meaning its regulation lies in a legal grey area and is not explicitly prohibited within any country. However, people may still be charged for its possession under certain circumstances such as under analogue laws due to its similarity to methcathinone, a widely prohibited substance, provided there is intent to sell or consume.


*'''China''' - As of October 2015 Ethylcathinone is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | accessdate=1 October 2015}}</ref>
*'''China''' - As of October 2015 Ethylcathinone is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | accessdate=1 October 2015}}</ref>