Editing 2C-D

{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477216133
| drug_name = 
| image = 2C-D 2DACS.svg
| width = 200px
| caption = 
| image2 = 2C-D-3d-sticks.png
| width2 = 175px

<!-- Clinical data -->
| pronounce = 
| tradename = 
| Drugs.com = 
| MedlinePlus = 
| licence_CA = 
| licence_EU = 
| DailyMedID = 
| licence_US = 
| pregnancy_AU = 
| pregnancy_category = 
| dependency_liability = 
| addiction_liability = 
| routes_of_administration = [[Oral administration|Oral]]
| class = [[Serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> receptor]] [[agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]
| ATC_prefix = 
| ATC_suffix = 

<!-- Legal status -->
| legal_AU = 
| legal_BR = F2
| legal_CA = Schedule III
| legal_DE = Anlage I
| legal_US = Schedule I
| legal_status = 

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = 
| metabolites = 
| onset = 
| elimination_half-life = 
| duration_of_action = 4–6 hours<ref name="Shulgin" />
| excretion = 

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 24333-19-5
| CAS_supplemental = 
| PubChem = 135740
| PubChemSubstance = 
| IUPHAR_ligand = 
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 119559
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7J43GY6ONS
| KEGG = 
| ChEBI = 
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 124049
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = 2,5-Dimethoxy-4-methyl-phenethylamine; 4-Methyl-2,5-dimethoxyphenethylamine; 2C-M; LE-25; LE25

<!-- Chemical data -->
| 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

<!-- Physical data -->
| 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 [[Psychedelics, dissociatives and deliriants|psychedelic drug]] of the [[2C (psychedelics)|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,<ref name="pmid5412084">{{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}}</ref> 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&nbsp;mg.<ref name=Shulgin>[https://www.erowid.org/library/books_online/pihkal/pihkal023.shtml 2C-D Entry in PiHKAL]</ref> Lower doses of 10 mg or less have been explored for [[Psychedelic microdosing|microdosing]].<ref>{{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  }}</ref> According to Shulgin, the effects of 2C-D typically last for 4–6 hours.<ref name=Shulgin/> 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 [[drug metabolism|metabolized]] by the [[monoamine oxidase]] (MAO) [[enzyme]]s [[MAO-A]] and [[MAO-B]].<ref name="DeanStellpflugBurnett2013">{{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 = }}</ref><ref name="TheobaldMaurer2007">{{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 = }}</ref> [[Monoamine oxidase inhibitor]]s (MAOIs) such as [[phenelzine]], [[tranylcypromine]], [[moclobemide]], and [[selegiline]] may potentiate the effects of 2C-D.<ref name="DeanStellpflugBurnett2013" /><ref name="TheobaldMaurer2007" /><ref name="HalmanKongSarris2024">{{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}}</ref> This may result in [[overdose]] and serious [[toxicity]].<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" />

==Pharmacology==
{| class="wikitable floatleft" style="font-size:small;"
|+ {{Nowrap|2C-D activities}}
|-
! [[Biological target|Target]] !! [[Affinity (pharmacology)|Affinity]] (K<sub>i</sub>, nM)
|-
| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || 440–1,630 (K<sub>i</sub>)<br />>10,000 ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}})<br /><25% ({{Abbrlink|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT1B receptor|5-HT<sub>1B</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT1D receptor|5-HT<sub>1D</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT1E receptor|5-HT<sub>1E</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT1F receptor|5-HT<sub>1F</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 23.9–32.4 (K<sub>i</sub>)<br />43.5–8,130 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />6–93% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2B receptor|5-HT<sub>2B</sub>]] || {{Abbr|ND|No data}} (K<sub>i</sub>)<br />230 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />77% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2C receptor|5-HT<sub>2C</sub>]] || 12.7–150 (K<sub>i</sub>)<br />71.1–18,600 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />48–100% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT3 receptor|5-HT<sub>3</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT4 receptor|5-HT<sub>4</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT5A receptor|5-HT<sub>5A</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT6 receptor|5-HT<sub>6</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT7 receptor|5-HT<sub>7</sub>]] || {{Abbr|ND|No data}}
|-
| [[Alpha-1A adrenergic receptor|α<sub>1A</sub>]] || 12,000
|-
| [[Alpha-1B adrenergic receptor|α<sub>1B</sub>]], [[Alpha-1D adrenergic receptor|α<sub>1D</sub>]] || {{Abbr|ND|No data}}
|-
| [[Alpha-2A adrenergic receptor|α<sub>2A</sub>]] || 290
|-
| [[Alpha-2B adrenergic receptor|α<sub>2B</sub>]], [[Alpha-2C adrenergic receptor|α<sub>2C</sub>]] || {{Abbr|ND|No data}}
|-
| [[Beta-1 adrenergic receptor|β<sub>1</sub>]]–[[Beta-3 adrenergic receptor|β<sub>3</sub>]] || {{Abbr|ND|No data}}
|-
| [[D1 receptor|D<sub>1</sub>]] || 24,000
|-
| [[D2 receptor|D<sub>2</sub>]] || 7,100
|-
| [[D3 receptor|D<sub>3</sub>]] || >17,000
|-
| [[D4 receptor|D<sub>4</sub>]] || {{Abbr|ND|No data}}
|-
| [[D5 receptor|D<sub>5</sub>]] || {{Abbr|ND|No data}}
|-
| [[H1 receptor|H<sub>1</sub>]] || >25,000
|-
| [[H2 receptor|H<sub>2</sub>]]–[[H4 receptor|H<sub>4</sub>]] || {{Abbr|ND|No data}}
|-
| [[Muscarinic acetylcholine M1 receptor|M<sub>1</sub>]]–[[Muscarinic acetylcholine M5 receptor|M<sub>5</sub>]] || {{Abbr|ND|No data}}
|-
| [[I1 receptor|I<sub>1</sub>]] || {{Abbr|ND|No data}}
|-
| [[Sigma-1 receptor|σ<sub>1</sub>]], [[Sigma-2 receptor|σ<sub>2</sub>]] || {{Abbr|ND|No data}}
|-
| {{Abbrlink|TAAR1|Trace amine-associated receptor 1}} || 3,500 (K<sub>i</sub>) (mouse)<br />150 (K<sub>i</sub>) (rat)<br />2,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (mouse)<br />490 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (rat)<br />>10,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (human)<br />61% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (mouse)<br />55% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (rat)
|-
| {{Abbrlink|SERT|Serotonin transporter}} || 31,000 (K<sub>i</sub>)<br />77,000 ({{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />{{Abbr|IA|Inactive}} ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|NET|Norepinephrine transporter}} || >30,000 (K<sub>i</sub>)<br />45,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />{{Abbr|IA|Inactive}} ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|DAT|Dopamine transporter}} || >30,000 (K<sub>i</sub>)<br />626,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />{{Abbr|IA|Inactive}} ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|MAO-A|Monoamine oxidase A}} || {{Abbr|ND|No data}} ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|-
| {{Abbrlink|MAO-B|Monoamine oxidase B}} || 24,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|- class="sortbottom"
| colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. '''Refs:''' <ref name="PDSPKiDatabase">{{cite web | title=Kᵢ Database | website=PDSP | date=16 March 2025 | url=https://pdsp.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14670&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D= | access-date=16 March 2025}}</ref><ref name="BindingDB">{{cite web | last=Liu | first=Tiqing | title=BindingDB BDBM50240787 2-(4-Methyl-2,5-dimethoxy-phenyl)-ethylamine::2-(4-methyl-2,5-dimethoxyphenyl)ethylamine::CHEMBL124049 | website=BindingDB | url=https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50240787 | access-date=16 March 2025}}</ref><ref name="RickliLuethiReinisch2015">{{cite journal | vauthors = Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME | title = Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs) | journal = Neuropharmacology | volume = 99 | issue = | pages = 546–553 | date = December 2015 | pmid = 26318099 | doi = 10.1016/j.neuropharm.2015.08.034 | url = https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf}}</ref><ref name="EshlemanForsterWolfrum2014">{{cite journal | vauthors = Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB | title = Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function | journal = Psychopharmacology (Berl) | volume = 231 | issue = 5 | pages = 875–888 | date = March 2014 | pmid = 24142203 | pmc = 3945162 | doi = 10.1007/s00213-013-3303-6 | url = https://www.researchgate.net/profile/Michael-Forster-2/publication/258061356_Behavioral_and_neurochemical_pharmacology_of_six_psychoactive_substituted_phenethylamines_Mouse_locomotion_rat_drug_discrimination_and_in_vitro_receptor_and_transporter_binding_and_function/links/53d119a00cf2f7e53cfbcd68/Behavioral-and-neurochemical-pharmacology-of-six-psychoactive-substituted-phenethylamines-Mouse-locomotion-rat-drug-discrimination-and-in-vitro-receptor-and-transporter-binding-and-function.pdf}}</ref><ref name="PottieCannaertStove2020">{{cite journal | vauthors = Pottie E, Cannaert A, Stove CP | title = In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor | journal = Arch Toxicol | volume = 94 | issue = 10 | pages = 3449–3460 | date = October 2020 | pmid = 32627074 | doi = 10.1007/s00204-020-02836-w | bibcode = 2020ArTox..94.3449P | url = | hdl = 1854/LU-8687071 | hdl-access = free }}</ref><ref name="MoyaBergGutiérrez-Hernandez2007" /><ref name="Acuña-CastilloVillalobosMoya2002" /><ref name="SimmlerBuchyChaboz2016">{{cite journal | vauthors = Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME | title = In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1 | journal = J Pharmacol Exp Ther | volume = 357 | issue = 1 | pages = 134–144 | date = April 2016 | pmid = 26791601 | doi = 10.1124/jpet.115.229765 | url = https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA | archive-url = https://web.archive.org/web/20250509235235/https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA | url-status = dead | archive-date = 2025-05-09 }}</ref>
|}

2C-D is a [[partial agonist]] of the [[serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub>]], [[5-HT2B receptor|5-HT<sub>2B</sub>]], and [[5-HT2C receptor|5-HT<sub>2C</sub> receptor]]s.<ref name="RickliLuethiReinisch2015" /><ref name="EshlemanForsterWolfrum2014" /><ref name="MoyaBergGutiérrez-Hernandez2007">{{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}}</ref><ref name="Acuña-CastilloVillalobosMoya2002">{{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 = }}</ref>

==Society and culture==
===Legal status===
====Canada====
As of October 31, 2016; 2C-D is a controlled substance (Schedule III) in Canada.<ref>{{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}}</ref>

====China====
As of October 2015 2C-D is a controlled substance in China.<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=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 }}</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 = Retsinformation}}</ref>

====Finland====
Listed in the government decree on psychoactive substances banned from the consumer market.<ref>{{cite web | url=https://www.finlex.fi/fi/lainsaadanto/2014/1130 | title=FINLEX ® - Ajantasainen lainsäädäntö: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014 }}</ref><ref>{{cite web | url=https://www.finlex.fi/fi/lainsaadanto/saadoskokoelma/2021/733 | title=FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 733/2021 }}</ref>

====Germany====
2C-D is an [[Drugs controlled by the German Betäubungsmittelgesetz|Anlage I]] controlled drug.

====Sweden====
[[Riksdag|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.<ref>{{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 }}</ref>

====United States====
2C-D became a [[Controlled Substances Act#Schedule I controlled substances|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.<ref>{{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 }}</ref> On a state level, both [[Oklahoma]] and [[Pennsylvania]] list 2C-D under schedule I.

==See also==
* [[ASR-2001]]

==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:2C (psychedelics)]]
[[Category:5-HT2A agonists]]
[[Category:5-HT2B agonists]]
[[Category:5-HT2C agonists]]
[[Category:Designer drugs]]
[[Category:Psychedelic phenethylamines]]
[[Category:Substances discovered in the 1970s]]
[[Category:TAAR1 agonists]]