2C-D
{{Infobox drug
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| verifiedrevid = 477216133
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| image = 2C-D 2DACS.svg
| width = 200px
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| image2 = 2C-D-3d-sticks.png
| width2 = 175px
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| routes_of_administration = Oral
| class = Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
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| legal_AU =
| legal_BR = F2
| legal_CA = Schedule III
| legal_DE = Anlage I
| legal_US = Schedule I
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| duration_of_action = 4–6 hours
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| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 24333-19-5
| CAS_supplemental =
| PubChem = 135740
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 119559
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7J43GY6ONS
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 124049
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| PDB_ligand =
| synonyms = 2,5-Dimethoxy-4-methyl-phenethylamine; 4-Methyl-2,5-dimethoxyphenethylamine; 2C-M; LE-25; LE25
| IUPAC_name = 2-(2,5-dimethoxy-4-methylphenyl)ethan-1-amine
| C=11 | H=17 | N=1 | O=2
| SMILES = O(c1cc(c(OC)cc1CCN)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H17NO2/c1-8-6-11(14-3)9(4-5-12)7-10(8)13-2/h6-7H,4-5,12H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UNQQFDCVEMVQHM-UHFFFAOYSA-N
| melting_point = 213
| melting_high = 214
| melting_notes = (hydrochloride)
}}
2C-D, also known as 2C-M or as 2,5-dimethoxy-4-methylphenethylamine, is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences,{{cite journal |vauthors=Ho BT, Tansey LW, Balster RL, An R, McIsaac WM, Harris RT |title=Amphetamine analogs. II. Methylated phenethylamines |journal=Journal of Medicinal Chemistry |volume=13 |issue=1 |pages=134–5 |date=January 1970 |pmid=5412084 |doi= 10.1021/jm00295a034}} and its activity was subsequently investigated in humans by Alexander Shulgin.
Use and effects
Not much information is known about the toxicity of 2C-D, as no major studies have been conducted. In his book PiHKAL, Shulgin lists the dosage range as being from 20 to 60 mg.[https://www.erowid.org/library/books_online/pihkal/pihkal023.shtml 2C-D Entry in PiHKAL] Lower doses of 10 mg or less have been explored for microdosing.{{Cite web|last=Nez|first=Hosteen|date=2015|title=Erowid 2C-D Vault : Smart Pills|url=https://www.erowid.org/chemicals/2cd/2cd_smartpills1.shtml|url-status=live|access-date=2022-01-09|website=www.erowid.org|archive-url = https://web.archive.org/web/20010709231503/http://www.erowid.org/chemicals/2cd/2cd_smartpills1.shtml |archive-date = 2001-07-09 }} According to Shulgin, the effects of 2C-D typically last for 4–6 hours. Shulgin himself referred to this substance as a “pharmacological tofu,” meaning that when mixed with other substances, it can extend or potentiate their effects without coloring the experience too much, in a manner similar to how tofu absorbs the flavors of sauces or spices it is cooked with. Hanscarl Leuner, working in Germany, explored the use of 2C-D under the name LE-25 in psychotherapeutic research.{{citation needed|date=November 2018}}
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
2C-D is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = J Med Toxicol | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x | url = }}{{cite journal | vauthors = Theobald DS, Maurer HH | title = Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series) | journal = Biochem Pharmacol | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 | url = }} Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-D.{{Cite journal |vauthors=Halman A, Kong G, Sarris J, Perkins D |date=January 2024 |title=Drug-drug interactions involving classic psychedelics: A systematic review |journal=J Psychopharmacol |volume=38 |issue=1 |pages=3–18 |doi=10.1177/02698811231211219 |pmc=10851641 |pmid=37982394}} This may result in overdose and serious toxicity.
Pharmacology
2C-D is a partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.{{cite journal | vauthors = Moya PR, Berg KA, Gutiérrez-Hernandez MA, Sáez-Briones P, Reyes-Parada M, Cassels BK, Clarke WP | title = Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors | journal = J Pharmacol Exp Ther | volume = 321 | issue = 3 | pages = 1054–1061 | date = June 2007 | pmid = 17337633 | doi = 10.1124/jpet.106.117507 | url = https://core.ac.uk/download/pdf/208315525.pdf}}{{cite journal | vauthors = Acuña-Castillo C, Villalobos C, Moya PR, Sáez P, Cassels BK, Huidobro-Toro JP | title = Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors | journal = Br J Pharmacol | volume = 136 | issue = 4 | pages = 510–519 | date = June 2002 | pmid = 12055129 | pmc = 1573376 | doi = 10.1038/sj.bjp.0704747 | url = }}
Society and culture
=Legal status=
==Canada==
As of October 31, 2016; 2C-D is a controlled substance (Schedule III) in Canada.{{Cite web|url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php|title=Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)|date=4 May 2016}}
==China==
As of October 2015 2C-D is a controlled substance in China.{{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=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}
==Denmark==
2C-D is added to the list of Schedule B controlled substances.{{cite web |url=https://www.retsinformation.dk/Forms/R0710.aspx?id=137169 |title = Retsinformation}}
==Finland==
Listed in the government decree on psychoactive substances banned from the consumer market.{{cite web | url=https://www.finlex.fi/fi/laki/ajantasa/2014/20141130 | title=FINLEX ® - Ajantasainen lainsäädäntö: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014 }}{{cite web | url=https://www.finlex.fi/fi/laki/alkup/2021/20210733 | title=FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 733/2021 }}
==Germany==
2C-D is an Anlage I controlled drug.
==Sweden==
Sveriges riksdags health ministry Statens folkhälsoinstitut classified 2C-D as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (Act on the Prohibition of Certain Goods Dangerous to Health) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as "2,5-dimetoxi-4-metylfenetylamin (2C-D)", making it illegal to sell or possess.{{cite web |last=Johansson |first=Morgan |url=http://www.notisum.se/rnp/sls/sfs/20050026.pdf |title=Svensk författningssamling |access-date=January 24, 2022 |archive-date=September 29, 2013 |archive-url=https://web.archive.org/web/20130929063138/http://www.notisum.se/rnp/sls/sfs/20050026.pdf |url-status=dead }}
==United States==
2C-D became a Schedule I Controlled Substance in the United States as of July 9, 2012, with the signing of Food and Drug Administration Safety and Innovation Act.{{Cite web |url=http://thomas.loc.gov/cgi-bin/query/z?c112:S.3187: |title=S. 3187 |access-date=2012-07-11 |archive-date=2012-12-14 |archive-url=https://web.archive.org/web/20121214091910/http://thomas.loc.gov/cgi-bin/query/z?c112:S.3187: |url-status=dead }} On a state level, both Oklahoma and Pennsylvania list 2C-D under schedule I.
See also
References
{{Reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/23 2C-D - Isomer Design]
- [https://psychonautwiki.org/wiki/2C-D 2C-D - PsychonautWiki]
- [https://erowid.org/chemicals/2cd/ 2C-D - Erowid]
- [https://erowid.org/library/books_online/pihkal/pihkal023.shtml 2C-D - PiHKAL - Erowid]
- [https://isomerdesign.com/pihkal/read/pk/23 2C-D - PiHKAL - Isomer Design]
- [https://tripsitter.com/2cd/ 2C-D: The Intersect Between DOM & 2C-B - Tripsitter]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{TAAR1 modulators}}
{{Phenethylamines}}
Category:Psychedelic phenethylamines