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2C-D: Difference between revisions
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'''2,5-Dimethoxy-4-methylphenethylamine''' (also known as '''2C-M''', '''LE-25''' and more commonly as '''2C-D''') is a synthetic [[Psychoactive class::psychedelic]] of the [[Chemical class::phenethylamine]] chemical class that produces short-lived [[psychedelic]] effects when [[routes of administration|administered]]. Its sensory and cognitive effects profile has been described as being the most similar to that of [[mescaline]] among members of the [[2C-x family]], albeit with a significantly shorter duration. | '''2,5-Dimethoxy-4-methylphenethylamine''' (also known as '''2C-M''', '''LE-25''' and more commonly as '''2C-D''') is a synthetic [[Psychoactive class::psychedelic]] of the [[Chemical class::phenethylamine]] chemical class that produces short-lived [[psychedelic]] effects when [[routes of administration|administered]]. Its sensory and cognitive effects profile has been described as being the most similar to that of [[mescaline]] among members of the [[2C-x family]], albeit with a significantly shorter duration. | ||
The synthesis of 2C-D was first published in 1970 by a team from the Texas Research Institute of Mental Sciences.<ref>Amphetamine analogs. II. Methylated phenethylamines | The synthesis of 2C-D was first published in 1970 by a team from the Texas Research Institute of Mental Sciences.<ref name="Ho1970">{{cite journal|title=Amphetamine analogs. II. Methylated phenethylamines|pmid=5412084|doi=10.1021/jm00295a034|year=1970|volume=13|issue=1|pages=134-135|first1=B. T.|last1=Ho|first2=L. W.|last2=Tansey|first3=R. L.|last3=Balster|first4=R.|last4=An|first5=W. M.|last5=McIsaac|first6=R. T.|last6=Harris|journal=Journal of Medicinal Chemistry|issn=0022-2623|eissn=1520-4804|oclc=39480771}}</ref> Initial trials by [[Alexander Shulgin]] at sub-threshold doses in humans were carried out in 1964.<ref name="Shulgin1976">{{cite book|author=Alexander Shulgin|author-link=Alexander Shulgin|title=Pharmacology Notes I (The Shulgin Lab Books)|publisher=Erowid|url=https://erowid.org/library/books_online/shulgin_labbooks/shulgin_labbook1_searchable.pdf|page=176|place=Lafayette, CA|year=1976}}</ref> | ||
Many anecdotal reports suggest that it is calmer, easier to handle and more comfortable on the body than other closely related [[psychedelic]] [[phenethylamines]]. While not especially visual or physically euphoric at common doses, it is reported to be very lucid, analytical and unimpaired in its headspace - a quality it retains even as the dose is increased. | Many anecdotal reports suggest that it is calmer, easier to handle and more comfortable on the body than other closely related [[psychedelic]] [[phenethylamines]]. While not especially visual or physically euphoric at common doses, it is reported to be very lucid, analytical and unimpaired in its headspace - a quality it retains even as the dose is increased. | ||
Lower doses of 2C-D (generally 10 mg or less) have been explored for its use as a potential [[nootropic]], albeit with mixed results.<ref>Lemaire | Lower doses of 2C-D (generally 10 mg or less) have been explored for its use as a potential [[nootropic]], albeit with mixed results.<ref>{{cite web|author=Darrell Lemaire|year=1990|orig-year=Updated 2015|publisher=Erowid|url=https://www.erowid.org/chemicals/2cd/2cd_smartpills1.shtml|title=Certain Exotic Transmitters as Smart Pills or Compounds that Increase the Capacity for Mental Work in Humans|access-date=October 11, 2020}}</ref> | ||
Today, 2C-D is used both recreationally and as an [[entheogen]]. It is rarely sold on the streets and almost exclusively distributed as a gray area [[research chemical]] by online vendors. | Today, 2C-D is used both recreationally and as an [[entheogen]]. It is rarely sold on the streets and almost exclusively distributed as a gray area [[research chemical]] by online vendors. | ||
==History and culture== | ==History and culture== | ||
The synthesis of 2C-D was first published in 1970 by a team from the Texas Research Institute of Mental Sciences,<ref | The synthesis of 2C-D was first published in 1970 by a team from the Texas Research Institute of Mental Sciences,<ref name="Ho1970"/>, but initial trials by [[Alexander Shulgin]] at sub-threshold doses were carried out in 1964. Further investigations at higher doses were carried out by Shulgin and his fellow researchers between 1974 and 1978.<ref name="Shulgin1976"/> The name '2C-D' derives from the chemical's structure - it is the 2-Carbon analogue of [[DOM]]. | ||
Shulgin notably referred to 2C-D as a “pharmacological tofu,” meaning it can extend or potentiate the effect of other substances without overly coloring the experience, in a manner similar to how tofu absorbs the flavors of sauces or spices it is cooked with.{{citation needed}} While some use this as evidence that 2C-D is relatively uninteresting as a psychedelic on its own, others strongly disagree with this assessment and hold that 2C-D is an unusually versatile and fully-fledged [[psychedelic]] in its own right. | Shulgin notably referred to 2C-D as a “pharmacological tofu,” meaning it can extend or potentiate the effect of other substances without overly coloring the experience, in a manner similar to how tofu absorbs the flavors of sauces or spices it is cooked with.{{citation needed}} While some use this as evidence that 2C-D is relatively uninteresting as a psychedelic on its own, others strongly disagree with this assessment and hold that 2C-D is an unusually versatile and fully-fledged [[psychedelic]] in its own right. | ||
Despite showing promise as a very functional psychostimulant<ref>Zuba | Despite showing promise as a very functional psychostimulant<ref>{{cite journal|last1=Zuba|first1=D.|last2=Sekuła|first2=K.|year=2013|title=Analytical characterization of three hallucinogenic N-(2-methoxy)benzyl derivatives of the 2C-series of phenethylamine drugs|journal=Drug Testing and Analysis|volume=5|issue=8|pages=634–645|doi=10.1002/dta.1397|pmid=22936468|issn=1942-7603|eissn=1942-7611|oclc=231680670}}</ref><ref>{{cite journal|last1=King|first1=L. A.|year=2014|title=New phenethylamines in Europe|journal=Drug Testing and Analysis|volume=6|issue=7–8|pages=808–818|doi=10.1002/dta.1570|pmid=24574327|issn=1942-7603|eissn=1942-7611|oclc=231680670}}</ref> with successful studies investigating the use in psychotherapy in Germany,<ref>{{cite book|last1=Schneider|first1=U.|first2=D.E.|last2=Dietrich|first3=U.|last3=Gast|year=2004|title=Aspekte des Psychischen: Festschrift anlässlich des 60. Geburtstags von Hinderk M. Emrich|location=Würzbug, Germany|publisher=Königshausen & Neumann|language=de|isbn=3826027299|oclc=55887990}}</ref> 2C-D has not found widespread use. This has been argued to be due to the previously limited diversity of substances on the market - a consumer dynamic which has changed significantly with the advent of the internet - allowing a broader freedom of choice for explorers of psychedelic phenethylamines.<ref>{{cite book|author=James Martin|year=2014|doi=10.1057/9781137399052|title=Drugs on the Dark Net: How Cryptomarkets are Transforming the Global Trade in Illicit Drugs|isbn=978-1-349-48566-6|oclc=903145880|publisher=Palgrave Macmillan|location=Basingstoke, UK|series=Palgrave pivot.}}</ref> Of these, it tends to be substantially harder to find and notably more expensive by weight.{{citation needed}} | ||
==Chemistry== | ==Chemistry== | ||
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==Legal status== | ==Legal status== | ||
*'''Australia''': Australia has a blanket ban over all substituted phenethylamines including the entire 2C-X family.<ref> | *'''Australia''': Australia has a blanket ban over all substituted phenethylamines including the entire 2C-X family.<ref>{{cite web|title=Psychoactive Substances|publisher=National Drug and Alcohol Research Centre|year=2014|url=https://comorbidity.edu.au/sites/default/files/cre/page/New%20Psychoactive%20Substances.pdf}}{{dead link|date=October 2020}}</ref> | ||
*'''Austria''': 2C-D is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).{{citation needed}} | *'''Austria''': 2C-D is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).{{citation needed}} | ||
*'''Brazil''': Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref> | *'''Brazil''': Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.<ref>{{cite web|url=http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7|title=RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016|publication-date=December 5, 2016|publisher=Agência Nacional de Vigilância Sanitária (ANVISA) [Brazilian Health Regulatory Agency (ANVISA)]|language=pt}}</ref> | ||
*'''Canada''': 2C-D would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.<ref> | *'''Canada''': 2C-D would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.<ref>{{cite web|url=http://isomerdesign.com/Cdsa/schedule.php?schedule=3§ion=ALL&structure=C|title=Schedule III|work=Controlled Drugs and Substances Act (CDSA)|publisher=Isomer Design|access-date=October 10, 2020}}</ref> | ||
*'''China''': 2C-D is a controlled substance in China as of October 2015.<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 | *'''China''': 2C-D is a controlled substance in China as of October 2015.<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=国家食品药品监督管理总局 [China Food and Drug Administration (CFDA)]|date=September 27, 2015|language=zh|archive-url=https://web.archive.org/web/20170906191704/http://www.sfda.gov.cn/WS01/CL0056/130753.html|archive-date=September 6, 2017}}</ref> | ||
*'''Denmark''': 2C-D is added to the list of Schedule B controlled substances.<ref> | *'''Denmark''': 2C-D is added to the list of Schedule B controlled substances.<ref>{{cite web|url=https://www.retsinformation.dk/Forms/R0710.aspx?id=137169|title=Bekendtgørelse om euforiserende stoffer|access-date=December 10, 2019|language=da|id=BEK Nr. 557|date=May 31, 2011|publisher=Civilstyrelsen [Civil Agency]}}</ref> | ||
*'''Germany''': 2C-D is controlled under Anlage I BtMG (Narcotics Act, Schedule I) | *'''Germany''': 2C-D is controlled under Anlage I BtMG (''Narcotics Act, Schedule I'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Gesetz über den Verkehr mit Betäubungsmitteln: Anlage I|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> as of December 13, 2014.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl114s1999.pdf|title=Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|work=Bundesgesetzblatt Jahrgang 2014 Teil I Nr. 57|page=1999-2002|publication-date=December 12, 2014|language=de|oclc=231871244|issn=0341-1095|date=December 5, 2014}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=Gesetz über den Verkehr mit Betäubungsmitteln: § 29|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> | ||
*'''Japan''': 2C-D is controlled by the Pharmaceutical Affairs Law in Japan, making it illegal to possess or sell.<ref>Analytical Data of Designated Substances (Shitei-Yakubutsu) Controlled by the Pharmaceutical | *'''Japan''': 2C-D is controlled by the Pharmaceutical Affairs Law in Japan, making it illegal to possess or sell.<ref>{{cite journal|title=Analytical Data of Designated Substances (Shitei-Yakubutsu) Controlled by the Pharmaceutical Affairs Law in Japan, Part I: GC-MS and LC-MS|url=https://www.erowid.org/references/texts/show/7395docid7635|language=ja|volume=128|issue=6|pages=971-979|journal=Yakugaku Zasshi|eissn=0031-6903|issn=1347-5231|oclc=909890652|year=2008|pmid=18520145|doi=10.1248/yakushi.128.981|first1=N.|last1=Uchiyama|first2=M.|last2=Kawamura|first3=H.|last3=Kamakura|first4=R.|last4=Kikura-Hanajiri|first5=Y.|last5=Goda}}</ref> | ||
*'''Latvia''': 2C-D is a Schedule I controlled substance.<ref> | *'''Latvia''': 2C-D 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> | ||
*'''Sweden''': 2C-D is classified as a health hazard as of March 1, 2005, in the regulation SFS 2005:26, making it illegal to sell or possess.<ref>Svensk författningssamling | http://www.notisum.se/rnp/sls/sfs/20050026.pdf</ref> | *'''Sweden''': 2C-D is classified as a health hazard as of March 1, 2005, in the regulation SFS 2005:26, making it illegal to sell or possess.<ref>{{cite web|title=Svensk författningssamling Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor|url=http://www.notisum.se/rnp/sls/sfs/20050026.pdf|id=SFS 2005:26|language=sv|date=February 3, 2005|publication-date=February 15, 2005|publisher=Läkemedelsverket [Swedish Medical Products Agency]|issn=1101-5225|work=Läkemedelsverkets författningssamling (LVFS)}}</ref> | ||
*'''Switzerland''': 2C-D is a controlled substance specifically named under Verzeichnis E.<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''': 2C-D is a controlled substance specifically named under Verzeichnis E.<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> | ||
*'''United Kingdom''': 2C-D is a Class A drug in the United Kingdom as a result of the phenethylamine catch-all clause.<ref> | *'''United Kingdom''': 2C-D is a Class A drug in the United Kingdom as a result of the phenethylamine catch-all clause.<ref>{{cite web|title=Schedule 2: Part I: Class A Drugs|url=http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I|work="Misuse of Drugs Act 1971"|access-date=August 20, 2020|publisher=UK Government}}</ref> | ||
*'''United States''': 2C-D is listed in Schedule I of section 202(c) of the Controlled Substances Act in the United States. This was signed into law as of July 2012 under the Food and Drug Administration Safety and Innovation Act.<ref> | *'''United States''': 2C-D is listed in Schedule I of section 202(c) of the Controlled Substances Act in the United States. This was signed into law as of July 2012 under the Food and Drug Administration Safety and Innovation Act.<ref>{{cite web|url=http://www.govtrack.us/congress/bills/112/s3187/text|title=S. 3187 (112<sup>th</sup>): Food and Drug Administration Safety and Innovation Act|date=June 27, 2012|access-date=October 10, 2020|publisher=GovTrack}}</ref> | ||
==See also== | ==See also== | ||