Talk:4-CA: Difference between revisions

Line 13:

==History and culture==

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.<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> 4-CA became a common tool for selective modification of the serotonergic function<ref name="Fuller1992~~"></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>

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.<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 risk due to neurotoxicity was too high.

==Chemistry==

Line 103:

*'''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 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.{{citation needed}}

*'''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>

*'''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=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl116s2615.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl116s2615.pdf%27%5D__1576017393518|title=Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|publisher=Bundesanzeiger Verlag|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}}

@@ Line 13: / Line 13: @@
 ==History and culture==
-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.<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>  4-CA became a common tool for selective modification of the serotonergic function<ref name="Fuller1992"></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>
+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.<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 risk due to neurotoxicity was too high.
 ==Chemistry==
@@ Line 103: / Line 103: @@
 *'''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 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.{{citation needed}}
-*'''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>
+*'''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=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl116s2615.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl116s2615.pdf%27%5D__1576017393518|title=Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|publisher=Bundesanzeiger Verlag|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}}