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 (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/5412084</ref> Initial trials by [[Alexander Shulgin]] at sub-threshold doses in humans were carried out in 1964.<ref>Shulgin, Alexander. "Pharmacology Lab Notes #1". Lafayette, CA. (1960-1976). p94, p175 (Erowid.org) | https://erowid.org/library/books_online/shulgin_labbooks/shulgin_labbook1_searchable.pdf</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">{{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, D. (1990). Erowid 2C-D Vault: Smart Pills, by Hosten & Lazar. Retrieved from https://www.erowid.org/chemicals/2cd/2cd_smartpills1.shtml</ref>
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>Amphetamine analogs. II. Methylated phenethylamines (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/5412084</ref>, 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>Shulgin, Alexander. "Pharmacology Lab Notes #1". Lafayette, CA. (1960-1976). p94, p175 (Erowid.org) | https://erowid.org/library/books_online/shulgin_labbooks/shulgin_labbook1_searchable.pdf</ref> The name '2C-D' derives from the chemical's structure - it is the 2-Carbon analogue of [[DOM]].
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, D., & Sekula, K. (2013). Analytical characterization of three hallucinogenic N-(2-methoxy)benzyl derivatives of the 2C-series of phenethylamine drugs. Drug Testing and Analysis, 5(8), 634–645. https://doi.org/10.1002/dta.1397</ref><ref>King, L. A. (2014). New phenethylamines in Europe. Drug Testing and Analysis, 6(7–8), 808–818. https://doi.org/10.1002/dta.1570</ref> with successful studies investigating the use in psychotherapy in Germany,<ref>Schneider, U. (2004). Aspekte des Psychischen: Festschrift anlässlich des 60. Geburtstags von Hinderk M. Emrich. Würzbug, Germany: Königshausen & Neumann. '''No complete fulltext was available at the time of writing, please refer to the Google Scholar document: https://books.google.de/books?id=yo45tYQj2-MC&lpg=PA129&ots=tW1EqmhrGF&dq=DMM-PEA&hl=de&pg=PA129&output=embed<nowiki/>.'''</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>Martin, J. (2014). Drugs on the Dark Net. London: Palgrave Macmillan UK. https://doi.org/10.1057/9781137399052</ref> Of these, it tends to be substantially harder to find and notably more expensive by weight.{{citation needed}}
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>New Psychoactive Substances (National Drug and Alcohol Research Centre 2014) | https://comorbidity.edu.au/sites/default/files/cre/page/New%20Psychoactive%20Substances.pdf</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). In its Schedule II, the further specifying NPSV (Neue-Psychoaktive-Substanzen-Verordnung Österreich) explicitly bans all substituted phenetylamines.<ref>{{cite web|url=https://www.ris.bka.gv.at/GeltendeFassung.wxe?Abfrage=Bundesnormen&Gesetzesnummer=20007642|title=Bundesrecht konsolidiert: Gesamte Rechtsvorschrift für Neue-Psychoaktive-Substanzen-Verordnung|date=June 26, 2019|language=de|access-date=January 10, 2021}}</ref>
*'''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>Controlled Drugs and Substances Act (S.C. 1996, c. 19) |http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-12.html#h-28</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&section=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 September 2015 | language=Chinese | accessdate=1 October 2015}}</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=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>Bekendtgørelse om euforiserende stoffer | https://www.retsinformation.dk/Forms/R0710.aspx?id=137169</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) as of December 13, 2014.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl114s1999.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl114s1999.pdf%27%5D__1576023093735|title=Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|access-date=December 10, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Anlage I BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 10, 2019|language=de}}</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=§ 29 BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 10, 2019|language=de}}</ref>
*'''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 AŠairs Law in Japan, Part I: GC-MS and LC-MS | https://www.erowid.org/references/texts/show/7395docid7635</ref>
*'''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>Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (2,5-Dimetoksifeniletānamīni) | http://likumi.lv/doc.php?id=121086</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>
*'''The Netherlands:''' 2C-D is currently legal, but it is part of a substance group that may be banned soon as part of a recently passed law on New Psychoactive Substances (NPS). <ref>{{Citation|title= Wijziging van de Opiumwet in verband met het toevoegen van een derde lijst met als doel het tegengaan van de productie van en de handel in nieuwe psychoactieve stoffen en enkele andere wijzigingen (Dutch) | year=2024|url=https://www.tweedekamer.nl/kamerstukken/wetsvoorstellen/detail?id=2022Z14042&dossier=36159}}</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. (1977). Misuse of Drugs Act 1971 (S.I. 1977/1243). London: The Stationery Office Limited. Retrieved July 5, 2017, from http://www.legislation.gov.uk/uksi/1977/1243/made</ref>
*'''Turkey:''' 2C-D is a classed as drug and is illegal to possess, produce, supply, or import.<ref>Bakanlar Kurulu Kararı Karar Sayısı : 2013/4827 | https://free-ankara.org/wp-content/uploads/2017/09/BKK_2013_4827_28688.pdf</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>S. 3187: Food and Drug Administration Safety and Innovation Act, Subtitle D-Synthetic Drugs | http://www.govtrack.us/congress/bills/112/s3187/text</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>{{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==
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{{#set:Featured=true}}


[[Category:Substance]]
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Hallucinogen]]
[[Category:Psychedelic]]
[[Category:Psychedelic]]
[[Category:Phenethylamine]]
[[Category:2C-x]]
[[Category:2C-x]]
Retrieved from "http://psy.st/wiki/2C-D"