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Talk:4-CA: Difference between revisions

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{{decree|type=notice|message=This article is in the 'Talk' namespace because it is an unfinished draft. This section is used to host drafts for unpublished articles as well as discussions for published ones. If you'd like to use this area to discuss this draft, please do so in the 'Discussion' section at the very bottom of the page. This notice will be removed once this draft has been approved for publication by an administrator.}}


{{headerpanel|{{Approval}}}}
{{headerpanel|{{Approval}}{{Warning/4-CA}}}}
{{Warning/4-CA}}
{{Distinguish|4-CMA}}
{{Distinguish|4-CMA|4-FA}}
{{SummarySheet}}
{{SummarySheet}}
{{SubstanceBox/4-CA}}
{{SubstanceBox/4-CA}}
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4-CA is known for its severe [[Releasing_agent#Neurotoxicity|neurotoxicity]] and was found to selectively destruct serotonergic neurons in animal study.<ref>{{cite journal|last1=Miller|first1=Krys J.|last2=Anderholm|first2=David C.|last3=Ames|first3=Matthew M.|date=1986|title=Metabolic activation of the serotonergic neurotoxin para-chloroamphetamine to chemically reactive intermediates by hepatic and brain microsomal preparations|journal=Biochemical Pharmacology|volume=35|issue=10|pages=1737-1742|doi=10.1016/0006-2952(86)90332-1|issn=0006-2952}}</ref>
4-CA is known for its severe [[Releasing_agent#Neurotoxicity|neurotoxicity]] and was found to selectively destruct serotonergic neurons in animal study.<ref>{{cite journal|last1=Miller|first1=Krys J.|last2=Anderholm|first2=David C.|last3=Ames|first3=Matthew M.|date=1986|title=Metabolic activation of the serotonergic neurotoxin para-chloroamphetamine to chemically reactive intermediates by hepatic and brain microsomal preparations|journal=Biochemical Pharmacology|volume=35|issue=10|pages=1737-1742|doi=10.1016/0006-2952(86)90332-1|issn=0006-2952}}</ref>


It is highly recommended to avoid the use of this substance and to use [[harm reduction]] practices if done anyway.
The use of this substance is strongly discouraged and it is recommended to use [[harm reduction]] practices if done anyway.


==History and culture==
==History and culture==
{{historyStub}}
 
In 1963, the effects of [[4-CMA]] were described by the Swiss researchers Pletscher, Burkard, Bruderer and Gey.<ref>{{cite journal|last1=Pletscher|first1=A.|last2=Burkard|first2=W.P.|last3=Bruderer|first3=H.|last4=Gey|first4=K.F.|date=1963|title=Decrease of cerebral 5-hydroxytryptamine and 5-hydroxyindolacetic acid by an arylalkylamine|journal=Life Sciences|volume=2|issue=11|pages=828-833|doi=10.1016/0024-3205(63)90094-8|issn=0024-3205}}</ref> Due to their results, several other chlorinated analogs of amphetamine, including 4-CA had been synthesized by the American pharmaceutical company Eli Lilly and Company. They were evaluated as appetite suppressants.<ref>{{cite journal|last1=Fuller|first1=Ray W.|date=1992|title=Effects of ''p''-chloroamphetamine on brain serotonin neurons|journal=Neurochemical Research|volume=17|issue=5|pages=449–456|doi=10.1007/BF00969891|issn=1573-6903}}</ref><ref>{{cite journal|last1=Owen Jr.|first1=John E.|date=1963|title=Psychopharmacological Studies of Some 1-(Chlorophenyl)-2-aminopropanes I: Effects on Appetitive-Controlled Behavior|journal=Journal of Pharmaceutical Sciences|volume=52|issue=7|pages=679-683|doi=10.1002/jps.2600520716|issn=0022-3549}}</ref> U.S. American biochemist Ray W. Fuller and collegues resynthesized these compounds and found that 4-CA was the most potent serotonin depletor.<ref>{{cite journal|last1=Fuller|first1=Ray W.|last2=Hines|first2=C.W.|last3=Mills|first3=J.|date=1965|title=Lowering of brain serotonin level by chloramphetamines|journal=Biochemical Pharmacology|volume=14|issue=4|pages=483-488|doi=10.1016/0006-2952(65)90221-2|issn=0006-2952}}</ref>  
In 1963, the effects of [[4-CMA]] were described by the Swiss researchers Pletscher, Burkard, Bruderer and Gey.<ref>{{cite journal|last1=Pletscher|first1=A.|last2=Burkard|first2=W.P.|last3=Bruderer|first3=H.|last4=Gey|first4=K.F.|date=1963|title=Decrease of cerebral 5-hydroxytryptamine and 5-hydroxyindolacetic acid by an arylalkylamine|journal=Life Sciences|volume=2|issue=11|pages=828-833|doi=10.1016/0024-3205(63)90094-8|issn=0024-3205}}</ref> Because of their results, several other chlorinated analogs of [[amphetamine]], including 4-CA had been synthesized by the American pharmaceutical company Eli Lilly and Company. They were examined as [[Appetite_suppression|appetite suppressants]].<ref name="Fuller1992">{{cite journal|last1=Fuller|first1=Ray W.|date=1992|title=Effects of ''p''-chloroamphetamine on brain serotonin neurons|journal=Neurochemical Research|volume=17|issue=5|pages=449–456|doi=10.1007/BF00969891|issn=1573-6903}}</ref><ref name="OwenJr1963>{{cite journal|last1=Owen Jr.|first1=John E.|date=1963|title=Psychopharmacological Studies of Some 1-(Chlorophenyl)-2-aminopropanes I: Effects on Appetitive-Controlled Behavior|journal=Journal of Pharmaceutical Sciences|volume=52|issue=7|pages=679-683|doi=10.1002/jps.2600520716|issn=0022-3549}}</ref> U.S. American biochemist Ray W. Fuller and collegues resynthesized these compounds and found that 4-CA was the most potent [[serotonin]] depletor.<ref>{{cite journal|last1=Fuller|first1=Ray W.|last2=Hines|first2=C.W.|last3=Mills|first3=J.|date=1965|title=Lowering of brain serotonin level by chloramphetamines|journal=Biochemical Pharmacology|volume=14|issue=4|pages=483-488|doi=10.1016/0006-2952(65)90221-2|issn=0006-2952}}</ref> Van Praag and others conducted comprehensive clinical study on humans in 1971, and it has been found to have a potent [[antidepressant]] effect. It was well tolerated and having only few side effects.<ref>{{cite journal|last1=van Praag|first1=H.M.|last2=Schut|first2=T.|last3=Bosma|first3=E.|last4=van den Bergh|first4=R.|date=1971|title=A comparative study of the therapeutic effects of some 4-chlorinated amphetamine derivatives in depressive patients|journal=Psychopharmacologia|volume=20|issue=1|pages=66–76|doi=10.1007/BF00404060|issn=1432-2072}}</ref><ref name="Shulgin1978"></ref> Yunger, McMaster, and Harvey described the related neurotoxicity in 1974.<ref name="Shulgin1978">{{cite book|last=Shulgin|first=Alexander T.|editor1-last=Iversen|editor1-first=Leslie L.|editor2-last=Iversen|editor2-first=Susan D.|editor3-last=Snyder|editor3-first=Solomon H.|date=1978|title=Handbook of Psychopharmacology|volume=Volume 11: Stimulants|url=https://www.erowid.org/archive/rhodium/chemistry/shulgin.pea.sar.hop.html#35|chapter=Chapter 6 |location=New York|publisher=Plenum Press,|page=313 et seq.|isbn=978-1-4757-0512-6|author-link=Alexander Shulgin}}</ref> 4-CA became a common tool for selective modification of the serotonergic function in laboratory animals.<ref name="Fuller1992"></ref> The research of its promising medical effects was halted because the risks due to neurotoxicity were too high.<ref name="Shulgin1978"></ref>


==Chemistry==
==Chemistry==
4-Chloroamphetamine is a synthetic compound of the [[substituted amphetamine]] class. Amphetamines 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. Amphetamines are alpha-methylated [[phenethylamines]]. 4-CA contains a chlorine atom at R4 of its phenyl ring and is a chlorinated analogue of [[amphetamine]].  
 
4-Chloroamphetamine is a synthetic compound of the [[substituted amphetamine]] class. Amphetamines 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. Amphetamines are alpha-methylated [[phenethylamines]]. 4-CA contains a chlorine atom at R4 of its phenyl ring and is a chlorinated analogue of [[amphetamine]].  
==Pharmacology==
==Pharmacology==
{{pharmacology}}
{{pharmacology}}
4-Chloroamphetamine acts as a [[releasing agent]] of the [[Monoamine_neurotransmitters|monoamine neurotransmitter]] [[serotonin]]. At higher doses, it can deplete brain serotonin.<ref name="Fuller1992"/>
A decreases in tryptophane hydroxylase activity could be observed.<ref>{{cite journal|last1=Sanders-Bush|first1=E.|last2=Bushing|first2=J.A.|last3=Sulser|first3=F.|date=1972|title=p-Chloroamphetamine—inhibition of cerebral tryptophan hydroxylase|journal=Biochemical Pharmacology|volume=21|issue=10|pages=1501-1510|doi=10.1016/0006-2952(72)90375-9|issn=0006-2952}}</ref>


==Subjective effects==
==Subjective effects==
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|{{effects/physical|
|{{effects/physical|
If applicable, a brief paragraph summary of the substance's physical effects may be included here.


You may select physical effects to add below [[Subjective effect index#Physical effects|here]].
You may select physical effects to add below [[Subjective effect index#Physical effects|here]].


*'''[[Effect::Physical effect]]'''  
*'''[[Effect::Abnormal heartbeat]]'''<ref name="SteinWaynerKantak1981>{{cite journal|last1=Stein|first1=J.M.|last2=Wayner|first2=M.J.|last3=Kantak|first3=K.M.|date=1981|title=Increased urination following p-chloroamphetamine|journal=Pharmacology Biochemistry and Behavior|volume=15|issue=2|pages=297-301|doi=10.1016/0091-3057(81)90191-X|issn=0091-3057}}</ref>
*'''[[Effect::Physical effect2]]'''
*'''[[Effect::Appetite suppression]]'''<ref name="OwenJr1963></ref><ref name="SteinWaynerKantakCook1978>{{cite journal|last1=Stein|first1=J.M.|last2=Wayner|first2=M.J.|last3=Kantak|first3=K.M.|last4=Cook|first4=R.C.|date=1978|title=Short- and long-term effects of para-chloroamphetamine on ingestive behavior|journal=Pharmacology Biochemistry and Behavior|volume=9|issue=1|pages=115-122|doi=10.1016/0091-3057(78)90021-7|issn=0091-3057}}</ref>
*'''[[Effect::Physical effect3]]'''
*'''[[Effect::Decreased blood pressure]]'''<ref name="SteinWaynerKantak1981></ref>
*'''[[Effect::Decreased heart rate]]'''<ref name="SteinWaynerKantak1981></ref>
*'''[[Effect::Dehydration]]'''<ref name="SteinWaynerKantakCook1978></ref>
*'''[[Effect::Difficulty urinating]]'''
*'''[[Effect::Dry mouth]]'''
*'''[[Effect::Frequent urination]]'''<ref name="SteinWaynerKantak1981></ref>
*'''[[Effect::Increased blood pressure]]'''<ref name="SteinWaynerKantak1981></ref>
*'''[[Effect::Increased bodily temperature]]'''<ref name="QuockWeick1979">{{cite journal|last1=Quock|first1=Raymond M.|last2=Weick|first2=Barton G.|date=1979|title=p‐Chloroamphetamine‐induced hyperthermia pharmacologically distinct from fenfluramine‐induced hyperthermia|journal=Journal of Pharmacy and Pharmacology|volume=31|issue=1|pages=27-32|doi=10.1111/j.2042-7158.1979.tb13416.x|issn=0022-3573}}</ref>
*'''[[Effect::Increased heart rate]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Increased salivation]]'''<ref name="SteinWaynerKantak1981></ref>
*'''[[Effect::Orgasm suppression]]'''
*'''[[Effect::Physical euphoria]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Stimulation]]'''<ref name="SteinWaynerKantak1981></ref>
*'''[[Effect::Teeth grinding]]'''
*'''[[Effect::Temperature regulation suppression]]'''
*'''[[Effect::Temporary erectile dysfunction]]'''
*'''[[Effect::Vibrating vision]]'''


}}
}}
{{effects/visual|
If applicable, a brief paragraph summary of the substance's visual effects may be included here.
You may select visual effects to add below [[Subjective effect index#Visual effects|here]].
====Enhancements====
*'''[[Effect::Visual acuity effect1]]'''
====Distortions====
*'''[[Effect::Visual distortion effect1]]'''
====[[Effect::Geometry]]====
If applicable, a brief paragraph summary describing the visual geometry produced by the substance may be included here.
====Hallucinatory states====
If applicable, a brief summary of the substance's visual effects profile may be written here.
*'''[[Effect::Hallucinatory states1]]'''
}}
|{{effects/cognitive|
|{{effects/cognitive|
If applicable, a brief paragraph summary of the substance's cognitive effects may be included here.
Not much ist known about the cognitive effects of 4-CA.</br>
 
You may select from a list of cognitive effects to add below [[Subjective effect index#Cognitive effects|here]].
 
*'''[[Effect::Cognitive effect1]]'''
*'''[[Effect::Cognitive effect2]]'''
*'''[[Effect::Cognitive effect3]]'''
 
}}
{{effects/auditory|
If applicable, a brief paragraph summary of the substance's auditory effects may be included here.
 
You may select from a list of auditory effects to add below [[Subjective effect index#Auditory effects|here]].
 
*'''[[Effect::Auditory effect1]]'''
*'''[[Effect::Auditory effect2]]'''
 
}}
}}
{{effects/multisensory|
{{effects/multisensory|
If applicable, a brief paragraph summary of the substance's multisensory effects may be included here.
Not much ist known about the multisensory effects of 4-CA.</br>
 
You may select from a list of multisensory effects to add below [[Subjective effect index#Multisensory effects|here]].
 
*'''[[Effect::Multisensory effect1]]'''
*'''[[Effect::Multisensory effect2]]'''
 
}}
}}
{{effects/transpersonal|
{{effects/transpersonal|
If applicable, a brief paragraph summary of the substance's transpersonal effects may be included here.
Not much ist known about the transpersonal effects of 4-CA.</br>
 
You may select from a list of transpersonal effects to add below [[Subjective effect index#Transpersonal effects|here]].
 
*'''[[Effect::Transpersonal effect1]]'''
*'''[[Effect::Transpersonal effect2]]'''
 
}}
}}
}}
}}
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There are currently {{#ask:[[Category:SUBSTANCE]][[Category:Experience]] | format=count}} experience reports which describe the effects of this substance in our [[experience index]].
There are currently {{#ask:[[Category:SUBSTANCE]][[Category:Experience]] | format=count}} experience reports which describe the effects of this substance in our [[experience index]].
{{#ask: [[Category:SUBSTANCE]][[Category:Experience]]|format=ul|Columns=1}}
{{#ask: [[Category:SUBSTANCE]][[Category:Experience]]|format=ul|Columns=1}}
Additional experience reports can be found here:
* [https://www.erowid.org/experiences/subs/exp_SUBSTANCE.shtml Erowid Experience Vaults: SUBSTANCE] <!-- Check the link to see if it exists -->
==Toxicity and harm potential==
==Toxicity and harm potential==
{{toxicity}}
{{toxicity}}
It is strongly recommended that one use [[responsible use|harm reduction practices]] when using this substance.
The use of this substance is strongly discouraged and it is recommended to use [[harm reduction]] practices if done anyway.
===Lethal dosage===
4-CA is known to induce heavy neurotoxicity
 
===Tolerance and addiction potential===
===Tolerance and addiction potential===
Not much is known about the tolerance and addiction potential.
===Dangerous interactions===
===Dangerous interactions===
{{DangerousInteractions}}
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Amphetamines}}
{{DangerousInteractions/Amphetamines}}
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==Legal status==
==Legal status==
{{LegalStub}}
{{LegalStub}}
*'''China''': 4-CA is a controlled substance in China.{{citation needed}}
*'''Australia''': 4-CA is a Schedule I controlled drug <ref>{{cite web|url=https://www.legislation.gov.au/Details/F2019L00561|title=Criminal Code Regulations 2019|publisher=Office of Parliamentary Counsel|access-date=December 12, 2019}}</ref>
*'''Germany''': 4-CA is controlled under the NpSG as it is a derivative of 2-phenethylamine.<ref>Anlage NpSG - Einzelnorm | https://www.gesetze-im-internet.de/npsg/anlage.html</ref> Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.<ref>§ 4 NpSG - Einzelnorm | https://www.gesetze-im-internet.de/npsg/__4.html</ref>
*'''Canada''': 4-CA is not explicitly listed on the CSDA.<ref>{{cite web|url=https://www.laws-lois.justice.gc.ca/eng/acts/C-38.8/page-13.html#docCont|title=Controlled Drugs and Substances Act - SCHEDULE I|publisher=Government of Canada|access-date=December 12, 2019}}</ref> However, as an analogue of amphetamine it is controlled as a Schedule I substance.<ref>{{cite web|url=https://isomerdesign.com/Cdsa/HC/StatusDecisions/A-2013-00235%20-%20PDFs/C-Chloroamphetamine%202005-07-21.pdf|title=STATUS DECISION OF CONTROLLED AND NON-CONTROLLED SUBSTANCE - Chloroamphetamine  |publisher=Health Canada|access-date=December 12, 2019}}</ref>
*'''China''': 4-CA 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|access-date=December 28, 2019|archive-url=https://web.archive.org/web/20170210033939/www.sfda.gov.cn/WS01/CL0056/130753.html|archive-date=February 10, 2017|language=zh}}</ref>
*'''Germany''': 4-CA is controlled under the NpSG (''New Psychoactive Substances Act'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 23, 2019|language=de}}</ref> as of November 26, 2016.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl116s2615.pdf|title=Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|publisher=Bundesanzeiger Verlag|work=Bundesgesetzblatt Jahrgang 2016 Teil I Nr. 55|publication-date=November 25, 2016|access-date=December 23, 2019|language=de}}</ref> Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 23, 2019|language=de}}</ref>
*'''United Kingdom''': 4-CA is treated as a Class A substance.{{citation needed}}
*'''United States''': 4-CA remains unscheduled.{{citation needed}}
*'''United States''': 4-CA remains unscheduled.{{citation needed}}
==See also==
==See also==
Retrieved from "https://psy.st/wiki/Talk:4-CA"
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