Chemistry:2C-N
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 150 mg or more, with a typical dose estimate of about 120 mg.[1][2] 2C-N is generally taken orally, and effects typically last 4 to 6 hours.[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
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
| 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 (EC50) 48% (Emax) |
| 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 |
| TAAR1 | >20,000 (Ki) (mouse) 340 (Ki) (rat) 15,000 (EC50) (mouse) 250 (EC50) (rat) >10,000 (EC50) (human) 28% (Emax) (mouse) 59% (Emax) (rat) |
| SERT | 32,000 (Ki) 154,000 (IC50) ND (EC50) |
| NET | >30,000 (Ki) 287,000 (IC50) ND (EC50) |
| DAT | >30,000 (Ki) >900,000 (IC50) ND (EC50) |
| MAO-A | ND (IC50) |
| MAO-B | 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, 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
- 2C (psychedelics)
- 25N-NBOMe
- 2C-CN
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml. 2C-N Entry in PiHKAL
- ↑ "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol 21 (10): 926–931. October 2018. doi:10.1093/ijnp/pyy047. PMID 29850881.
- ↑ 3.0 3.1 3.2 "2C or not 2C: phenethylamine designer drug review". J Med Toxicol 9 (2): 172–178. June 2013. doi:10.1007/s13181-013-0295-x. PMID 23494844.
- ↑ 4.0 4.1 "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)". Biochem Pharmacol 73 (2): 287–297. January 2007. doi:10.1016/j.bcp.2006.09.022. PMID 17067556.
- ↑ 5.0 5.1 "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol 38 (1): 3–18. January 2024. doi:10.1177/02698811231211219. PMID 37982394.
- ↑ "Kᵢ Database". 10 May 2025. 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=.
- ↑ 7.0 7.1 "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)". Neuropharmacology 99: 546–553. December 2015. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. 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.
- ↑ "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun 14 (1). December 2023. doi:10.1038/s41467-023-44016-1. PMID 38102107. Bibcode: 2023NatCo..14.8221W.
- ↑ 9.0 9.1 "Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors". J Pharmacol Exp Ther 321 (3): 1054–61. June 2007. doi:10.1124/jpet.106.117507. PMID 17337633.
- ↑ "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases". Drug Test Anal 11 (2): 318–324. February 2019. doi:10.1002/dta.2494. PMID 30188017. 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.
- ↑ "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther 357 (1): 134–144. April 2016. doi:10.1124/jpet.115.229765. PMID 26791601. 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.
- ↑ "Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors". Br J Pharmacol 136 (4): 510–519. June 2002. doi:10.1038/sj.bjp.0704747. PMID 12055129.
- ↑ "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016. http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php.
- ↑ "Lists of: Scheduling Actions, Controlled Substances, Regulated Chemicals". Drug Enforcement Administration. April 2022. https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf.
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