2C-N: Difference between revisions

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| NIAID_ChemDB =  
| NIAID_ChemDB =  
| PDB_ligand =  
| PDB_ligand =  
| synonyms = 2,5-Dimethoxy-4-nitrophenethylamine; 4-Nitro-2,5-dimethoxyphenethylamine
| synonyms = 25N; 2,5-Dimethoxy-4-nitrophenethylamine; 4-Nitro-2,5-dimethoxyphenethylamine


<!-- Chemical data -->
<!-- Chemical data -->
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(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>
(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>
==Interactions==
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
2C drugs like 2C-N are known to be [[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 drugs like 2C-N.<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==
==Pharmacology==
{| class="wikitable floatleft" style="font-size:small;"
===Pharmacodynamics===
{| class="wikitable floatright" style="font-size:small;"
|+ {{Nowrap|2C-N activities}}
|+ {{Nowrap|2C-N activities}}
|-
|-
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| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || 1,450–2,200
| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || 1,450–2,200
|-
|-
| [[5-HT1B receptor|5-HT<sub>1B</sub>]] || <10,000
| [[5-HT1B receptor|5-HT<sub>1B</sub>]] || >10,000
|-
|-
| [[5-HT1D receptor|5-HT<sub>1D</sub>]] || 832
| [[5-HT1D receptor|5-HT<sub>1D</sub>]] || 832
Line 119: Line 125:
| [[Alpha-1A adrenergic receptor|α<sub>1A</sub>]] || >15,000
| [[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-1B adrenergic receptor|α<sub>1B</sub>]], [[Alpha-1D adrenergic receptor|α<sub>1D</sub>]] || >10,000
|-
| [[Alpha-2A adrenergic receptor|α<sub>2A</sub>]] || 240–1,300
|-
|-
| [[Alpha-2A adrenergic receptor|α<sub>2A</sub>]] || 1,300
| [[Alpha-2B adrenergic receptor|α<sub>2B</sub>]] || 2,240
|-
|-
| [[Alpha-2B adrenergic receptor|α<sub>2B</sub>]], [[Alpha-2C adrenergic receptor|α<sub>2C</sub>]] || {{Abbr|ND|No data}}
| [[Alpha-2C adrenergic receptor|α<sub>2C</sub>]] || 891
|-
|-
| [[Beta-1 adrenergic receptor|β<sub>1</sub>]]–[[Beta-3 adrenergic receptor|β<sub>3</sub>]] || {{Abbr|ND|No data}}
| [[Beta-1 adrenergic receptor|β<sub>1</sub>]]–[[Beta-3 adrenergic receptor|β<sub>3</sub>]] || >10,000
|-
|-
| [[D1 receptor|D<sub>1</sub>]] || 19,000
| [[D1 receptor|D<sub>1</sub>]] || 19,000
|-
|-
| [[D2 receptor|D<sub>2</sub>]] || 6,100
| [[D2 receptor|D<sub>2</sub>]] || 6,100–>10,000
|-
|-
| [[D3 receptor|D<sub>3</sub>]] || 20,000
| [[D3 receptor|D<sub>3</sub>]] || 20,000
|-
|-
| [[D4 receptor|D<sub>4</sub>]], [[D5 receptor|D<sub>5</sub>]] || {{Abbr|ND|No data}}
| [[D4 receptor|D<sub>4</sub>]], [[D5 receptor|D<sub>5</sub>]] || >10,000
|-
|-
| [[H1 receptor|H<sub>1</sub>]] || >25,000
| [[H1 receptor|H<sub>1</sub>]] || >25,000
|-
|-
| [[H2 receptor|H<sub>2</sub>]]–[[H4 receptor|H<sub>4</sub>]] || {{Abbr|ND|No data}}
| [[H2 receptor|H<sub>2</sub>]] || >10,000
|-
| [[H3 receptor|H<sub>3</sub>]] || 5,500
|-
| [[H4 receptor|H<sub>4</sub>]] || >10,000
|-
|-
| [[Muscarinic acetylcholine M1 receptor|M<sub>1</sub>]]–[[Muscarinic acetylcholine M5 receptor|M<sub>5</sub>]] || {{Abbr|ND|No data}}
| [[Muscarinic acetylcholine M1 receptor|M<sub>1</sub>]]–[[Muscarinic acetylcholine M5 receptor|M<sub>5</sub>]] || >10,000
|-
|-
| [[I1 receptor|I<sub>1</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}}
| [[Sigma-1 receptor|σ<sub>1</sub>]], [[Sigma-2 receptor|σ<sub>2</sub>]] || >10,000
|-
| [[Opioid receptor|{{Abbr|ORs|Opioid receptors (MOR, DOR, and KOR)}}]] || >10,000
|-
|-
| {{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|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)
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===Synthesis===
===Synthesis===
2C-N is synthesized by the mixed acid nitration of [[2C-H]] using [[sulfuric acid]] and [[nitric acid]].<ref name="PiHKAL"/>
2C-N is synthesized by the mixed acid nitration of [[2C-H]] using [[sulfuric acid]] and [[nitric acid]].<ref name="PiHKAL"/>
==History==
2C-N was first described in the [[scientific literature]] by at least 1991.<ref name="PiHKAL" />


==Society and culture==
==Society and culture==
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==See also==
==See also==
* [[2C (psychedelics)]]
* [[2C (psychedelics)]]
* [[25N-NBOMe]]
* [[2C-CN]]


==References==
==References==
{{Reflist}}
{{Reflist}}
==External links==
* [https://isomerdesign.com/pihkal/explore/34 2C-N - Isomer Design]
* [https://www.bluelight.org/xf/threads/409157 The Big & Dandy 2C-N Thread - Bluelight]


{{Psychedelics}}
{{Psychedelics}}

Latest revision as of 00:39, 21 June 2025

Template:Main other <templatestyles src="Infobox drug/styles.css"/> Script error: No such module "Infobox".Template:Template otherScript error: No such module "TemplatePar".{{Infobox drug/maintenance categoriesTemplate:Yesno | drug_name = | INN = | _drugtype =

| _has_physiological_data= | _has_gene_therapy=

| vaccine_type= | mab_type= | _number_of_combo_chemicals=Script error: No such module "ParameterCount". | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=101424[O-][N+](=O)c1cc(OC)c(cc1OC)CCN1S/C10H14N2O4/c1-15-9-6-8(12(13)14)10(16-2)5-7(9)3-4-11/h5-6H,3-4,11H2,1-2H3ZMUSDZGRRJGRAO-UHFFFAOYSA-NTemplate:StdinchiciteTemplate:Stdinchicite | _combo_data= | _physiological_data= | _clinical_data= Oral[1]Serotonin; 5-HT2 receptor agonist; Serotonergic psychedelic; HallucinogenNone | _legal_data=

| _other_data=2-(2,5-dimethoxy-4-nitrophenyl)ethan-1-amine

| _image_0_or_2 = 2C-N 2DACS.svg2C-N-3d-sticks.png | _image_LR =

| _datapage = 2C-N (data page) | _vaccine_target=_type_not_vaccine | _legal_all= | _ATC_prefix_supplemental=None | _has_EMA_link = | CAS_number=261789-00-8 | PubChem=10036637 | ChemSpiderID=8212202 | ChEBI= | ChEMBL= | DrugBank= | KEGG= | _hasInChI_or_Key=yes | UNII=BB2B23B11H | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =

| _countSecondIDs=Script error: No such module "ParameterCount". | _countIndexlabels=Script error: No such module "ParameterCount". | _trackListSortletter= |QID = |QID2 = |Verifiedfields=verified |Watchedfields=verified |verifiedrevid=477216300}}

2C-N, also known as 2,5-dimethoxy-4-nitrophenethylamine, is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin.[1]

Use

Shulgin, in his book PiHKAL, as well as other sources, list the dosage range as 100 to 150Template:Nbspmg or more, with a typical dose estimate of about 120Template:Nbspmg.[1][2] 2C-N is generally taken orally, and effects typically last 4 to 6Template:Nbsphours.[1]

Effects

Shulgin accounts his experiences after ingesting 2C-N:[1]

(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.

Interactions

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2C drugs like 2C-N are known to be metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.[3][4] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs like 2C-N.[3][4][5] This may result in overdose and serious toxicity.[5][3]

Pharmacology

Pharmacodynamics

2C-N activities
Target Affinity (Ki, nM)
5-HT1A 1,450–2,200
5-HT1B >10,000
5-HT1D 832
5-HT1E 676
5-HT1F ND
5-HT2A 23.5–72.4 (Ki)
170 (Template:Abbrlink)
48% (Template:Abbrlink)
5-HT2B 123 (Ki)
730 (EC50)
74% (Emax)
5-HT2C 162–370 (Ki)
ND (EC50)
ND (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A >10,000
5-HT6 251
5-HT7 >10,000
α1A >15,000
α1B, α1D >10,000
α2A 240–1,300
α2B 2,240
α2C 891
β1–β3 >10,000
D1 19,000
D2 6,100–>10,000
D3 20,000
D4, D5 >10,000
H1 >25,000
H2 >10,000
H3 5,500
H4 >10,000
M1–M5 >10,000
I1 ND
σ1, σ2 >10,000
ORs >10,000
Template:Abbrlink >20,000 (Ki) (mouse)
340 (Ki) (rat)
15,000 (EC50) (mouse)
250 (EC50) (rat)
>10,000 (EC50) (human)
28% (Emax) (mouse)
59% (Emax) (rat)
Template:Abbrlink 32,000 (Ki)
154,000 (Template:Abbrlink)
ND (EC50)
Template:Abbrlink >30,000 (Ki)
287,000 (IC50)
ND (EC50)
Template:Abbrlink >30,000 (Ki)
>900,000 (IC50)
ND (EC50)
Template:Abbrlink ND (IC50)
Template:Abbrlink 66,000 (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [6][7][8][9][10][11]

2C-N is a low-potency partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[7][9][12]

Chemistry

The full name of the chemical is 2-(2,5-dimethoxy-4-nitrophenyl)ethanamine.

Salts of 2C-N have a bright yellow to orange color due to the presence of the nitro group,Script error: No such module "Unsubst". 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.[1]

History

2C-N was first described in the scientific literature by at least 1991.[1]

Society and culture

Legal status

Canada

As of October 31, 2016, 2C-N is a controlled substance (Schedule III) in Canada.[13]

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.[14]

See also

References

Template:Reflist

External links

Template:Psychedelics Template:Serotonin receptor modulators Template:TAAR modulators Script error: No such module "Navbox".

  1. ↑ a b c d e f g Template:CitePiHKAL 2C-N Entry in PiHKAL
  2. ↑ Script error: No such module "Citation/CS1".
  3. ↑ a b c Script error: No such module "Citation/CS1".
  4. ↑ a b Script error: No such module "Citation/CS1".
  5. ↑ a b Script error: No such module "Citation/CS1".
  6. ↑ Script error: No such module "citation/CS1".
  7. ↑ a b Script error: No such module "Citation/CS1".
  8. ↑ Script error: No such module "Citation/CS1".
  9. ↑ a b Script error: No such module "Citation/CS1".
  10. ↑ Script error: No such module "Citation/CS1".
  11. ↑ Script error: No such module "Citation/CS1".
  12. ↑ Script error: No such module "Citation/CS1".
  13. ↑ Script error: No such module "citation/CS1".
  14. ↑ Script error: No such module "citation/CS1".
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