2C-N

2C-N

Clinical data
Other names	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
IUPAC name 2-(2,5-dimethoxy-4-nitrophenyl)ethan-1-amine
CAS Number	261789-00-8^Y
PubChem CID	10036637
ChemSpider	8212202^Y
UNII	BB2B23B11H
CompTox Dashboard (EPA)	DTXSID80180798
Chemical and physical data
Formula	C10H14N2O4
Molar mass	226.232 g·mol^−1
3D model (JSmol)	Interactive image
SMILES [O-][N+](=O)c1cc(OC)c(cc1OC)CCN
InChI 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^Y Key:ZMUSDZGRRJGRAO-UHFFFAOYSA-N^Y
(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]

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.

Pharmacology

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 (EC50Tooltip half-maximal effective concentration) 48% (EmaxTooltip 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	ND
α2A	1,300
α2B, α2C	ND
β1–β3	ND
D1	19,000
D2	6,100
D3	20,000
D4, D5	ND
H1	>25,000
H2–H4	ND
M1–M5	ND
I1	ND
σ1, σ2	ND
TAAR1Tooltip 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)
SERTTooltip Serotonin transporter	32,000 (Ki) 154,000 (IC50Tooltip half-maximal inhibitory concentration) ND (EC50)
NETTooltip Norepinephrine transporter	>30,000 (Ki) 287,000 (IC50) ND (EC50)
DATTooltip Dopamine transporter	>30,000 (Ki) >900,000 (IC50) ND (EC50)
MAO-ATooltip Monoamine oxidase A	ND (IC50)
MAO-BTooltip Monoamine oxidase 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: [3][4][5][6][7][8]

2C-N is a low-potency partial agonist of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[4][6][9]

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,^{[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]

Society and culture

Legal status

Canada

As of October 31, 2016, 2C-N is a controlled substance (Schedule III) in Canada.^[10]

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.^[11]

See also

• 2C (psychedelics)

References

1. 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. "Kᵢ Database". PDSP. 10 May 2025. Retrieved 10 May 2025.
4. 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.
5. 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. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.
6. 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.
7. 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.
8. 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.
9. 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.
10. "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.
11. "Lists of: Scheduling Actions, Controlled Substances, Regulated Chemicals" (PDF). Diversion Control Division. Drug Enforcement Administration. April 2022.