2C-N

Last updated
2C-N
2C-N 2DACS.svg
2C-N-3d-sticks.png
Clinical data
Other names25N; 2,5-Dimethoxy-4-nitrophenethylamine; 4-Nitro-2,5-dimethoxyphenethylamine
Routes of
administration 		Oral [1]
Drug class Serotonin; 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action 4–6 hours [1]
Identifiers
  • 2-(2,5-dimethoxy-4-nitrophenyl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C10H14N2O4
Molar mass 226.232 g·mol−1
3D model (JSmol)
  • [O-][N+](=O)c1cc(OC)c(cc1OC)CCN
  • InChI=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 Yes check.svgY
  • Key:ZMUSDZGRRJGRAO-UHFFFAOYSA-N Yes check.svgY
   (verify)

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]

Contents

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

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 (EC50 Tooltip half-maximal effective concentration)
48% (Emax Tooltip maximal efficacy)
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 Tooltip Trace amine-associated receptor 1>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 Tooltip Serotonin transporter32,000 (Ki)
154,000 (IC50 Tooltip half-maximal inhibitory concentration)
ND (EC50)
NET Tooltip Norepinephrine transporter>30,000 (Ki)
287,000 (IC50)
ND (EC50)
DAT Tooltip Dopamine transporter>30,000 (Ki)
>900,000 (IC50)
ND (EC50)
MAO-A Tooltip Monoamine oxidase AND (IC50)
MAO-B Tooltip Monoamine oxidase B66,000 (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-nitro phenyl)ethanamine.

Salts of 2C-N have a bright yellow to orange color due to the presence of the nitro group,[ citation needed ] 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

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

  1. 1 2 3 4 5 6 7 8 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. 2C-N Entry in PiHKAL
  2. ↑ Luethi D, Liechti ME (October 2018). "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. doi:10.1093/ijnp/pyy047. PMC   6165951 . PMID   29850881.
  3. 1 2 3 Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC   3657019 . PMID   23494844.
  4. 1 2 Theobald DS, Maurer HH (January 2007). "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. doi:10.1016/j.bcp.2006.09.022. PMID   17067556.
  5. 1 2 Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC   10851641 . PMID   37982394.
  6. ↑ "Kᵢ Database". PDSP. 10 May 2025. Retrieved 10 May 2025.
  7. 1 2 Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID   26318099.
  8. ↑ 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 (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun. 14 (1) 8221. Bibcode:2023NatCo..14.8221W. doi:10.1038/s41467-023-44016-1. PMC   10724237 . PMID   38102107.
  9. 1 2 Moya PR, Berg KA, Gutiérrez-Hernandez MA, Sáez-Briones P, Reyes-Parada M, Cassels BK, Clarke WP (June 2007). "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. doi:10.1124/jpet.106.117507. PMID   17337633.
  10. ↑ Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR (February 2019). "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases" (PDF). Drug Test Anal. 11 (2): 318–324. doi:10.1002/dta.2494. PMID   30188017.
  11. ↑ Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1" (PDF). J Pharmacol Exp Ther. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID   26791601. Archived from the original (PDF) on 9 May 2025.
  12. ↑ Acuña-Castillo C, Villalobos C, Moya PR, Sáez P, Cassels BK, Huidobro-Toro JP (June 2002). "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. doi:10.1038/sj.bjp.0704747. PMC   1573376 . PMID   12055129.
  13. ↑ "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.
  14. ↑ "Lists of: Scheduling Actions, Controlled Substances, Regulated Chemicals" (PDF). Diversion Control Division. Drug Enforcement Administration. April 2022.
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