Editing 2C-N

{{Infobox drug
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 477216300
| drug_name = 
| image = 2C-N 2DACS.svg
| width = 200px
| caption = 
| image2 = 2C-N-3d-sticks.png
| width2 = 200px
| caption2 = 

<!-- 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]]<ref name="PiHKAL"/>
| class = [[Serotonin]]; [[5-HT2 receptor|5-HT<sub>2</sub> receptor]] [[agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]
| ATC_prefix = None
| ATC_suffix = 

<!-- Legal status -->
| legal_status = 

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

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 261789-00-8
| CAS_supplemental = 
| PubChem = 10036637
| PubChemSubstance = 
| IUPHAR_ligand = 
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8212202
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BB2B23B11H
| KEGG = 
| ChEBI = 
| ChEMBL = 
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = 2,5-Dimethoxy-4-nitrophenethylamine; 4-Nitro-2,5-dimethoxyphenethylamine

<!-- Chemical data -->
| IUPAC_name = 2-(2,5-dimethoxy-4-nitrophenyl)ethan-1-amine
| C=10 | H=14 | N=2 | O=4 
| SMILES = [O-][N+](=O)c1cc(OC)c(cc1OC)CCN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H14N2O4/c1-15-9-6-8(12(13)14)10(16-2)5-7(9)3-4-11/h5-6H,3-4,11H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZMUSDZGRRJGRAO-UHFFFAOYSA-N
}}

'''2C-N''', also known as '''2,5-dimethoxy-4-nitrophenethylamine''', is a [[psychedelic drug|psychedelic]] [[substituted phenethylamine|phenethylamine]] of the [[2C (psychedelics)|2C]] family.  It was first synthesized by [[Alexander Shulgin]].<ref name="PiHKAL">{{CitePiHKAL}} [http://www.erowid.org/library/books_online/pihkal/pihkal034.shtml 2C-N Entry in ''PiHKAL'']</ref>

==Use==
Shulgin, in his book ''[[PiHKAL]]'', as well as other sources, list the dosage range as 100 to 150{{nbsp}}mg or more, with a typical dose estimate of about 120{{nbsp}}mg.<ref name="PiHKAL"/><ref name="LuethiLiechti2018">{{cite journal | vauthors = Luethi D, Liechti ME | title = Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics | journal = Int J Neuropsychopharmacol | volume = 21 | issue = 10 | pages = 926–931 | date = October 2018 | pmid = 29850881 | pmc = 6165951 | doi = 10.1093/ijnp/pyy047 | url = https://bitnest.netfirms.com/external/10.1093/ijnp/pyy047}}</ref> 2C-N is generally taken [[oral administration|orally]], and effects typically last 4 to 6{{nbsp}}hours.<ref name="PiHKAL"/>

==Effects==
Shulgin accounts his experiences after ingesting 2C-N:<ref name="PiHKAL" />

<blockquote>(with 120 mg) This came on very fast--I was aware of it within a half hour, and it got as far as it would go by an hour. There are similarities to MDMA, but missing is the benign anti-stress component. I am light-headed, and there just might be a little eye wiggling. And then it dropped right off to nothing within a couple of hours.

(with 150 mg) There may have been some visual changes, I'm not sure. But the talking was extremely easy. If there were no other things to use, this would be excellent, but there are other compounds available. This doesn't have too high a priority.

(with 150 mg) Am I enjoying it? Not exactly, but I am in a good mood. There is not the light-filled energy that some other materials can provide. By six hours, pretty much baseline. Strange material, but okay. Final score: body +3, mind +2, barely.</blockquote>

==Pharmacology==
{| class="wikitable floatleft" style="font-size:small;"
|+ {{Nowrap|2C-N activities}}
|-
! [[Biological target|Target]] !! [[Affinity (pharmacology)|Affinity]] (K<sub>i</sub>, nM)
|-
| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || 1,450–2,200
|-
| [[5-HT1B receptor|5-HT<sub>1B</sub>]] || <10,000
|-
| [[5-HT1D receptor|5-HT<sub>1D</sub>]] || 832
|-
| [[5-HT1E receptor|5-HT<sub>1E</sub>]] || 676
|-
| [[5-HT1F receptor|5-HT<sub>1F</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 23.5–72.4 (K<sub>i</sub>)<br />170 ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}})<br />48% ({{Abbrlink|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2B receptor|5-HT<sub>2B</sub>]] || 123 (K<sub>i</sub>)<br />730 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />74% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2C receptor|5-HT<sub>2C</sub>]] || 162–370 (K<sub>i</sub>)<br />{{Abbr|ND|No data}} ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />{{Abbr|ND|No data}} ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT3 receptor|5-HT<sub>3</sub>]] || >10,000
|-
| [[5-HT4 receptor|5-HT<sub>4</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT5A receptor|5-HT<sub>5A</sub>]] || >10,000
|-
| [[5-HT6 receptor|5-HT<sub>6</sub>]] || 251
|-
| [[5-HT7 receptor|5-HT<sub>7</sub>]] || >10,000
|-
| [[Alpha-1A adrenergic receptor|α<sub>1A</sub>]] || >15,000
|-
| [[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>]] || 1,300
|-
| [[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>]] || 19,000
|-
| [[D2 receptor|D<sub>2</sub>]] || 6,100
|-
| [[D3 receptor|D<sub>3</sub>]] || 20,000
|-
| [[D4 receptor|D<sub>4</sub>]], [[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}} || >20,000 (K<sub>i</sub>) (mouse)<br />340 (K<sub>i</sub>) (rat)<br />15,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (mouse)<br />250 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (rat)<br />>10,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (human)<br />28% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (mouse)<br />59% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (rat)
|-
| {{Abbrlink|SERT|Serotonin transporter}} || 32,000 (K<sub>i</sub>)<br />154,000 ({{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />{{Abbr|ND|No data}} ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|NET|Norepinephrine transporter}} || >30,000 (K<sub>i</sub>)<br />287,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />{{Abbr|ND|No data}} ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|DAT|Dopamine transporter}} || >30,000 (K<sub>i</sub>)<br />>900,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />{{Abbr|ND|No data}} ({{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}} || 66,000 ({{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=10 May 2025 | url=https://pdspdb.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=14674&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D= | access-date=10 May 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="WallachCaoCalkins2023">{{cite journal | vauthors = Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD | title = Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential | journal = Nat Commun | volume = 14 | issue = 1 | pages = 8221 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 | url = https://bitnest.netfirms.com/external/10.1038/s41467-023-44016-1}}</ref><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 = 1054–61 | date = June 2007 | pmid = 17337633 | doi = 10.1124/jpet.106.117507 | url = }}</ref><ref name="WagmannBrandtStratford2019">{{cite journal | vauthors = Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR | title = Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases | journal = Drug Test Anal | volume = 11 | issue = 2 | pages = 318–324 | date = February 2019 | pmid = 30188017 | doi = 10.1002/dta.2494 | url =https://publikationen.sulb.uni-saarland.de/bitstream/20.500.11880/29219/1/Interactions%20of%20phenethylamine-derived%20psychoactive%20substances%20of%20the%202C-series%20with%20human%20monoamine%20oxidases_mit_Vorblatt.pdf }}</ref><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://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}}</ref>
|}

2C-N is a low-[[potency (pharmacology)|potency]] [[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">{{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="MoyaBergGutiérrez-Hernandez2007" /><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>

==Chemistry==
The full name of the chemical is 2-(2,5-di[[methoxy]]-4-[[nitro compound|nitro]][[phenyl]])ethanamine.

[[Salt (chemistry)|Salts]] of 2C-N have a bright yellow to orange color due to the presence of the [[nitro functional group|nitro]] group,{{citation needed|date=September 2019}} unlike all other members of the 2C family in which the salts are white.

===Synthesis===
2C-N is synthesized by the mixed acid nitration of [[2C-H]] using [[sulfuric acid]] and [[nitric acid]].<ref name="PiHKAL"/>

==Society and culture==
===Legal status===
====Canada====
As of October 31, 2016, 2C-N 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>

====United Kingdom====
2C-N and most (possibly all) other compounds featured in PiHKAL are illegal drugs in the United Kingdom.

====United States====
In the United States, 2C-N is a Schedule 1 controlled substance.<ref>{{cite web |title=Lists of: Scheduling Actions, Controlled Substances, Regulated Chemicals |url=https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf |website=Diversion Control Division |publisher=Drug Enforcement Administration |date=April 2022}}</ref>

==See also==
* [[2C (psychedelics)]]

==References==
{{Reflist}}

{{Psychedelics}}
{{Serotonin receptor modulators}}
{{TAAR modulators}}
{{Phenethylamines}}

[[Category:2C (psychedelics)]]
[[Category:5-HT2A agonists]]
[[Category:5-HT2B agonists]]
[[Category:5-HT2C agonists]]
[[Category:Nitrobenzene derivatives]]
[[Category:Psychedelic phenethylamines]]
[[Category:TAAR1 agonists]]