DOC: Difference between revisions
>LockPicker revised references |
>Larnaca |
||
(6 intermediate revisions by 5 users not shown) | |||
Line 11: | Line 11: | ||
==History and culture== | ==History and culture== | ||
{{historyStub}} | {{historyStub}} | ||
DOC was first synthesized by 1972 by Ronald Coutts and Jerry Malicky at the University of Alberta.<ref name="Coutts1973"/> While human usage was popularized by the 1991 publication of its synthesis and pharmacology in [[PiHKAL]] ("Phenethylamines I Have Known And Loved")<ref name="PiHKAL"/> by [[Alexander Shulgin]], a 1989 forensic analysis of designer amphetamine samples identified DOC in Canadian drug seizures.<ref name="Dawson1989"/> | DOC was first synthesized by 1972 by Ronald Coutts and Jerry Malicky at the University of Alberta.<ref name="Coutts1973" /> While human usage was popularized by the 1991 publication of its synthesis and pharmacology in [[PiHKAL]] ("Phenethylamines I Have Known And Loved")<ref name="PiHKAL" /> by [[Alexander Shulgin]], a 1989 forensic analysis of designer amphetamine samples identified DOC in Canadian drug seizures.<ref name="Dawson1989" /> | ||
==Chemistry== | ==Chemistry== | ||
DOC or 4-chloro-2,5-dimethoxy-amphetamine, is a molecule of the [[substituted amphetamine]] class. Amphetamines are substituted phenethylamines containing a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain and a methyl group bound to the alpha carbon R<sub>α</sub>. DOC contains methoxy functional groups OCH<sub>3</sub> attached to carbons R<sub>2</sub> and R<sub>5</sub> and a chlorine atom attached to carbon R<sub>4</sub> of the phenyl ring. DOC is the amphetamine analogue of the phenethylamine [[2C-C]].<ref name="PiHKAL"/> | DOC or 4-chloro-2,5-dimethoxy-amphetamine, is a molecule of the [[substituted amphetamine]] class. Amphetamines are substituted phenethylamines containing a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain and a methyl group bound to the alpha carbon R<sub>α</sub>. DOC contains methoxy functional groups OCH<sub>3</sub> attached to carbons R<sub>2</sub> and R<sub>5</sub> and a chlorine atom attached to carbon R<sub>4</sub> of the phenyl ring. DOC is the amphetamine analogue of the phenethylamine [[2C-C]].<ref name="PiHKAL" /> | ||
DOC is a substituted alpha-methylated phenethylamine, a class of compounds commonly known as amphetamines. The phenethylamine equivalent (lacking the alpha-methyl group) is 2C-C. DOC has a stereocenter and (''R'')-(−)-DOC is the more active stereoisomer. | |||
==Pharmacology== | ==Pharmacology== | ||
{{Further|Serotonergic psychedelic}} | {{Further|Serotonergic psychedelic}} | ||
DOC acts as a selective 5-HT<sub>2A</sub>, 5-HT<sub>2B</sub>, and 5-HT<sub>2C</sub> receptor partial agonist. Its psychedelic effects are mediated via its actions on the 5-HT<sub>2A</sub> receptor. | |||
DOC's [[psychedelic]] effects are believed to come from its efficacy at the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] as a [[Agonist#Agonists|partial agonist]]. However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive. | DOC's [[psychedelic]] effects are believed to come from its efficacy at the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] as a [[Agonist#Agonists|partial agonist]]. However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive. | ||
Line 133: | Line 137: | ||
{{#ask: [[Category:DOC]][[Category:Experience]]|format=ul|Columns=1}} | {{#ask: [[Category:DOC]][[Category:Experience]]|format=ul|Columns=1}} | ||
Additional experience reports can be found here: | Additional experience reports can be found here: | ||
* [https://erowid.org/experiences/subs/exp_DOC.shtml Erowid Experience Vaults: DOC] | |||
*[https://erowid.org/experiences/subs/exp_DOC.shtml Erowid Experience Vaults: DOC] | |||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
Line 146: | Line 151: | ||
===Tolerance and addiction potential=== | ===Tolerance and addiction potential=== | ||
DOC is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating. | DOC is [[Addiction potential::not habit-forming]], and the desire to use it can actually decrease with use. It is most often self-regulating. | ||
Tolerance to the effects of DOC | Tolerance to the effects of DOC is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). DOC presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of DOC all psychedelics will have a reduced effect. | ||
===Overdose=== | ===Overdose=== | ||
Line 155: | Line 160: | ||
===Dangerous interactions=== | ===Dangerous interactions=== | ||
{{DangerousInteractions/Intro}} | {{DangerousInteractions/Intro}} | ||
{{DangerousInteractions/Psychedelics}} | |||
==Legal status== | ==Legal status== | ||
Line 173: | Line 175: | ||
*'''Latvia''': DOC is a Schedule I controlled substance.<ref>{{cite web|url=http://likumi.lv/doc.php?id=121086|title=Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem|publisher=VSIA Latvijas Vēstnesis|access-date=January 1, 2020|publication-date=November 10, 2005|language=lv}}</ref> | *'''Latvia''': DOC is a Schedule I controlled substance.<ref>{{cite web|url=http://likumi.lv/doc.php?id=121086|title=Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem|publisher=VSIA Latvijas Vēstnesis|access-date=January 1, 2020|publication-date=November 10, 2005|language=lv}}</ref> | ||
*'''New Zealand''': DOC is a Class C drug in New Zealand.{{citation needed}} | *'''New Zealand''': DOC is a Class C drug in New Zealand.{{citation needed}} | ||
*'''Netherlands:''' Possession, production and sale is illegal. | |||
*'''Switzerland''': DOC can be considered a controlled substance as a defined derivative of a-Methylphenethylamine under Verzeichnis E point 130. It is legal when used for scientific or industrial use.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | *'''Switzerland''': DOC can be considered a controlled substance as a defined derivative of a-Methylphenethylamine under Verzeichnis E point 130. It is legal when used for scientific or industrial use.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | ||
*'''Turkey:''' DOC is a classed as drug and is illegal to possess, produce, supply, or import.<ref>{{cite web|title=Bakanlar Kurulu Kararı - Karar Sayısı : 2013/5742|url=https://resmigazete.gov.tr/eskiler/2014/01/20140125-3.htm|publisher=Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü [General Directorate of Legislation Development and Publication]|publication-date=January 25, 2014|date=December 16, 2013|language=tr}}</ref><ref>{{cite web|title=Kararnamenin Eki: Liste|url=https://resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf|publisher=Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü [General Directorate of Legislation Development and Publication]|publication-date=January 25, 2014|date=December 16, 2013|language=tr|id=2013/5742|work=Resmî Gazete, Sayı: 28893}}</ref> | *'''Turkey:''' DOC is a classed as drug and is illegal to possess, produce, supply, or import.<ref>{{cite web|title=Bakanlar Kurulu Kararı - Karar Sayısı : 2013/5742|url=https://resmigazete.gov.tr/eskiler/2014/01/20140125-3.htm|publisher=Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü [General Directorate of Legislation Development and Publication]|publication-date=January 25, 2014|date=December 16, 2013|language=tr}}</ref><ref>{{cite web|title=Kararnamenin Eki: Liste|url=https://resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf|publisher=Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü [General Directorate of Legislation Development and Publication]|publication-date=January 25, 2014|date=December 16, 2013|language=tr|id=2013/5742|work=Resmî Gazete, Sayı: 28893}}</ref> | ||
Line 179: | Line 182: | ||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Psychedelics]] | *[[Psychedelics]] | ||
Line 186: | Line 190: | ||
==External links== | ==External links== | ||
*[http://en.wikipedia.org/wiki/2,5-Dimethoxy-4-chloroamphetamine DOC (Wikipedia)] | *[http://en.wikipedia.org/wiki/2,5-Dimethoxy-4-chloroamphetamine DOC (Wikipedia)] | ||
*[http://www.erowid.org/chemicals/doc/doc.shtml DOC (Erowid Vault)] | *[http://www.erowid.org/chemicals/doc/doc.shtml DOC (Erowid Vault)] | ||
*[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=64 DOC (PiHKAL / Isomer Design)] | *[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=64 DOC (PiHKAL / Isomer Design)] | ||
===Discussion=== | ===Discussion=== | ||
*[http://www.bluelight.org/vb/threads/286886-The-Big-amp-Dandy-DOC-Thread-(Part-1) The Big & Dandy DOC Thread (Part 1) (Bluelight)] | *[http://www.bluelight.org/vb/threads/286886-The-Big-amp-Dandy-DOC-Thread-(Part-1) The Big & Dandy DOC Thread (Part 1) (Bluelight)] | ||