3-FEA: Difference between revisions

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{{headerpanel|{{approval}}}}

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~~| ''[[3-FEA/Summary|Summary sheet: 3-FEA]]''~~

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'''3-Fluoroethamphetamine''' (also known as '''3-FEA''') is a novel synthetic ring-substituted fluorinated [[chemical class::amphetamine]] compound that produces a combination of [[psychoactive class::entactogen|entactogenic]] [[psychoactive class::stimulant]] effects when [[Routes of administration|administered]]. 3-FEA is structurally related to a series of [[designer drug|designer]] fluorinated [[substituted amphetamine]]s that originally included compounds such as [[2-FA]], [[2-FMA]], [[3-FA]], [[4-FMA]], [[4-FA]].<ref>Quednow, B., Girreser, U., Junge, T., & Ro, P. (2005). Isomeric Fluoro-methoxy-phenylalkylamines: a new series of controlled-substance analogues (designer drugs), 148, 143–156. https://doi.org/10.1016/j.forsciint.2004.05.003</ref>

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[[File:samphetamine.png|thumb|right|245px|thumb|right|243px||Generic structure of an amphetamine molecule]]

3-Fluoroethamphetamine, or 3-FEA, is a synthetic molecule of the amphetamine chemical class. Molecules of the amphetamine class contain a [[phenethylamine]] core comprised of a phenyl ring bound to an amino (NH2) group through an ethyl chain substituted with a methyl group at Rα (i.e. amphetamines are '''a'''lpha-'''m'''ethylated '''phe'''ne'''t'''hyl'''amines'''). 3-FEA is the 3-position fluorinated analog of ethylamphetamine (also known as ethamphetamine). It is also an analog of fenfluramine (which was withdrawn from the market after links between long term use and serotonin-2b receptor-induced heart valve damage was discovered) with the 3-trifluoromethyl group replaced with a 3-fluoro substituent.{{citation needed}}

3-Fluoroethamphetamine, or 3-FEA, is a synthetic molecule of the amphetamine chemical class. Molecules of the amphetamine class contain a [[phenethylamine]] core comprised of a phenyl ring bound to an amino (NH2) group through an ethyl chain substituted with a methyl group at Rα (i.e. amphetamines are '''a'''lpha-'''m'''ethylated '''phe'''ne'''t'''hyl'''amines''').

3-FEA is the 3-position fluorinated analog of ethylamphetamine (also known as ethamphetamine). It is also an analog of fenfluramine (which was withdrawn from the market after links between long term use and serotonin-2b receptor-induced heart valve damage was discovered) with the 3-trifluoromethyl group replaced with a 3-fluoro substituent.{{citation needed}}

==Pharmacology==

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Notably, it has been demonstrated that "compared to the unsubstituted ethylamphetamine, 3-fluoroethamphetamine is a weaker releaser of noradrenaline, but a stronger releaser of both dopamine and serotonin, and produced the strongest reinforcing effects in animal studies out of a range of 3-substituted amphetamine derivatives tested, despite not being the most potent dopamine releaser"<ref>Tessel RE, Woods JH. Structural relationship between meta-substituted N-ethylamphetamines and self-administration in rhesus monkeys. ''Pharmacologist'' 1974;16:142.</ref><ref>Tessel RE, Rutledge CO. Specificity of release of biogenic amines from isolated rat brain tissue as a function of the meta substituent of N-ethylamphetamine derivatives. ''The Journal of Pharmacology and Experimental Therapeutics'' 1976;15:142.</ref><ref>Tessel RE, Woods JH. Substituted N-ethylamphetamine self injection responding in the rhesus monkey: structure-activity relationships. ''The Journal of Pharmacology and Experimental Therapeutics'' 1978; 2: 274–81.</ref>

This indicates that 3-FEA effectively increases the levels of all the three major [[monoamine neurotransmitters]] dopamine, norepinephrine, and serotonin in the brain by binding to and partially [[Reuptake inhibitor|blocking the transporter proteins]] that normally clear those molecules from the [[synaptic cleft]] after they have fulfilled their function of conducting a neural impulse. This allows these molecules to accumulate within core regions of the brain to extra-endogenous levels, resulting in a combination of [[~~Relaxation~~|relaxing]], [[stimulating]], motivational and physically and cognitively [[euphoria|euphoric]] effects associated with [[entactogen]]ic [[substituted amphetamines]] like [[MDMA]] or other fluorinated amphetamines like [[4-FA]].{{citation needed}}

This indicates that 3-FEA effectively increases the levels of all the three major [[monoamine neurotransmitters]] dopamine, norepinephrine, and serotonin in the brain by binding to and partially [[Reuptake inhibitor|blocking the transporter proteins]] that normally clear those molecules from the [[synaptic cleft]] after they have fulfilled their function of conducting a neural impulse. This allows these molecules to accumulate within core regions of the brain to extra-endogenous levels, resulting in a combination of [[Muscle relaxation|relaxing]], [[stimulating]], motivational and physically and cognitively [[euphoria|euphoric]] effects associated with [[entactogen]]ic [[substituted amphetamines]] like [[MDMA]] or other fluorinated amphetamines like [[4-FA]].{{citation needed}}

==Subjective effects==

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Additional experience reports can be found here:

* [https://www.erowid.org/experiences/subs/exp_3FEA.shtml Erowid Experience Vaults: 3-FEA]

==Potential dangerous interactions==

*'''[[Stimulants]]''' - 3-FEA can be potentially dangerous in combination with other [[stimulant]]s as it can [[increased heart rate|increase one's heart rate]] and [[increased blood pressure|blood pressure]] to dangerous levels.

*'''[[MDMA]]''' - The neurotoxic effects of MDMA may be increased when combined with [[amphetamine]]s.

*'''[[Cocaine]]''' - This combination may increase strain on the heart to dangerous levels.

==Toxicity and harm potential==

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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>

==~~=Dangerous interactions===~~

==Legality==

~~{{DangerousInteractions/Intro}}~~

~~{{DangerousInteractions/MAOI|nt=dopamine}}~~

*'''[[Stimulants]]''' - 3-FEA can be potentially dangerous in combination with other [[stimulant]]s as it can [[increased heart rate|increase one's heart rate]] and [[increased blood pressure|blood pressure]] to dangerous levels.

~~{{DangerousInteractions/Stimulants}}~~

*'''[[MDMA]]''' - The neurotoxic effects of MDMA may be increased when combined with [[amphetamine]]s.

*'''[[Cocaine]]''' - This combination may increase strain on the heart to dangerous levels.

~~==Legal issues~~==

3-FEA is currently a grey area compound within all parts of the world, meaning its regulation lies in a legal grey area and that it is not known to be specifically illegal ("scheduled") within any country. However, people may still be charged for its possession under certain circumstances such as under analogue laws and with intent to sell or consume.

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*[[3-FA]]

*[[3-FMA]]

*[[4-FMA]]

==External links==

@@ Line 1: / Line 1: @@
 {{headerpanel|{{approval}}}}
 {{SubstanceBox/3-FEA}}
-{|
+{{SummarySheet}}
-|-
-|-
-| ''[[3-FEA/Summary|Summary sheet: 3-FEA]]''
-|}
 '''3-Fluoroethamphetamine''' (also known as '''3-FEA''') is a novel synthetic ring-substituted fluorinated [[chemical class::amphetamine]] compound that produces a combination of [[psychoactive class::entactogen|entactogenic]] [[psychoactive class::stimulant]] effects when [[Routes of administration|administered]]. 3-FEA is structurally related to a series of [[designer drug|designer]] fluorinated [[substituted amphetamine]]s that originally included compounds such as [[2-FA]], [[2-FMA]], [[3-FA]], [[4-FMA]], [[4-FA]].<ref>Quednow, B., Girreser, U., Junge, T., & Ro, P. (2005). Isomeric Fluoro-methoxy-phenylalkylamines: a new series of controlled-substance analogues (designer drugs), 148, 143–156. https://doi.org/10.1016/j.forsciint.2004.05.003</ref>
@@ Line 17: / Line 13: @@
 [[File:samphetamine.png|thumb|right|245px|thumb|right|243px||Generic structure of an amphetamine molecule]]
--Fluoroethamphetamine, or 3-FEA, is a synthetic molecule of the amphetamine chemical class. Molecules of the amphetamine class contain a [[phenethylamine]] core comprised of a phenyl ring bound to an amino (NH2) group through an ethyl chain substituted with a methyl group at Rα (i.e. amphetamines are '''a'''lpha-'''m'''ethylated '''phe'''ne'''t'''hyl'''amines'''). 3-FEA is the 3-position fluorinated analog of ethylamphetamine (also known as ethamphetamine). It is also an analog of fenfluramine (which was withdrawn from the market after links between long term use and serotonin-2b receptor-induced heart valve damage was discovered) with the 3-trifluoromethyl group replaced with a 3-fluoro substituent.{{citation needed}}
+-Fluoroethamphetamine, or 3-FEA, is a synthetic molecule of the amphetamine chemical class. Molecules of the amphetamine class contain a [[phenethylamine]] core comprised of a phenyl ring bound to an amino (NH2) group through an ethyl chain substituted with a methyl group at Rα (i.e. amphetamines are '''a'''lpha-'''m'''ethylated '''phe'''ne'''t'''hyl'''amines''').
+-FEA is the 3-position fluorinated analog of ethylamphetamine (also known as ethamphetamine). It is also an analog of fenfluramine (which was withdrawn from the market after links between long term use and serotonin-2b receptor-induced heart valve damage was discovered) with the 3-trifluoromethyl group replaced with a 3-fluoro substituent.{{citation needed}}
 ==Pharmacology==
@@ Line 24: / Line 22: @@
 Notably, it has been demonstrated that "compared to the unsubstituted ethylamphetamine, 3-fluoroethamphetamine is a weaker releaser of noradrenaline, but a stronger releaser of both dopamine and serotonin, and produced the strongest reinforcing effects in animal studies out of a range of 3-substituted amphetamine derivatives tested, despite not being the most potent dopamine releaser"<ref>Tessel RE, Woods JH. Structural relationship between meta-substituted N-ethylamphetamines and self-administration in rhesus monkeys. ''Pharmacologist'' 1974;16:142.</ref><ref>Tessel RE, Rutledge CO. Specificity of release of biogenic amines from isolated rat brain tissue as a function of the meta substituent of N-ethylamphetamine derivatives. ''The Journal of Pharmacology and Experimental Therapeutics'' 1976;15:142.</ref><ref>Tessel RE, Woods JH. Substituted N-ethylamphetamine self injection responding in the rhesus monkey: structure-activity relationships. ''The Journal of Pharmacology and Experimental Therapeutics'' 1978; 2: 274–81.</ref>
-This indicates that 3-FEA effectively increases the levels of all the three major [[monoamine neurotransmitters]] dopamine, norepinephrine, and serotonin in the brain by binding to and partially [[Reuptake inhibitor|blocking the transporter proteins]] that normally clear those molecules from the [[synaptic cleft]] after they have fulfilled their function of conducting a neural impulse. This allows these molecules to accumulate within core regions of the brain to extra-endogenous levels, resulting in a combination of [[Relaxation|relaxing]], [[stimulating]], motivational and physically and cognitively [[euphoria|euphoric]] effects associated with [[entactogen]]ic [[substituted amphetamines]] like [[MDMA]] or other fluorinated amphetamines like [[4-FA]].{{citation needed}}
+This indicates that 3-FEA effectively increases the levels of all the three major [[monoamine neurotransmitters]] dopamine, norepinephrine, and serotonin in the brain by binding to and partially [[Reuptake inhibitor|blocking the transporter proteins]] that normally clear those molecules from the [[synaptic cleft]] after they have fulfilled their function of conducting a neural impulse. This allows these molecules to accumulate within core regions of the brain to extra-endogenous levels, resulting in a combination of [[Muscle relaxation|relaxing]], [[stimulating]], motivational and physically and cognitively [[euphoria|euphoric]] effects associated with [[entactogen]]ic [[substituted amphetamines]] like [[MDMA]] or other fluorinated amphetamines like [[4-FA]].{{citation needed}}
 ==Subjective effects==
@@ Line 76: / Line 74: @@
 Additional experience reports can be found here:
 * [https://www.erowid.org/experiences/subs/exp_3FEA.shtml Erowid Experience Vaults: 3-FEA]
+==Potential dangerous interactions==
+{{DangerousInteractions/Intro}}
+{{DangerousInteractions/MAOI|nt=dopamine}}
+*'''[[Stimulants]]''' - 3-FEA can be potentially dangerous in combination with other [[stimulant]]s as it can [[increased heart rate|increase one's heart rate]] and [[increased blood pressure|blood pressure]] to dangerous levels.
+{{DangerousInteractions/Stimulants}}
+*'''[[MDMA]]''' - The neurotoxic effects of MDMA may be increased when combined with [[amphetamine]]s.
+*'''[[Cocaine]]''' - This combination may increase strain on the heart to dangerous levels.
 ==Toxicity and harm potential==
@@ Line 94: / Line 100: @@
 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>
-===Dangerous interactions===
+==Legality==
-{{DangerousInteractions/Intro}}
-{{DangerousInteractions/MAOI|nt=dopamine}}
-*'''[[Stimulants]]''' - 3-FEA can be potentially dangerous in combination with other [[stimulant]]s as it can [[increased heart rate|increase one's heart rate]] and [[increased blood pressure|blood pressure]] to dangerous levels.
-{{DangerousInteractions/Stimulants}}
-*'''[[MDMA]]''' - The neurotoxic effects of MDMA may be increased when combined with [[amphetamine]]s.
-*'''[[Cocaine]]''' - This combination may increase strain on the heart to dangerous levels.
-==Legal issues==
 {{legalStub}}
 -FEA is currently a grey area compound within all parts of the world, meaning its regulation lies in a legal grey area and that it is not known to be specifically illegal ("scheduled") within any country. However, people may still be charged for its possession under certain circumstances such as under analogue laws and with intent to sell or consume.
@@ Line 120: / Line 118: @@
 *[[3-FA]]
 *[[3-FMA]]
-*[[4-FMA]]
 ==External links==