2C-N

2C-N, also known as 4-nitro-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.^[1] It is taken orally.^[1]

2C-N

Clinical data
Other names	25N; 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
Onset of action	≤30 minutes[1]
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
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2C-N was first synthesized by Alexander Shulgin and was described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-N's dose range as 100 to 150 mg or more orally and a duration of 4 to 6 hours.^[1][2] It has an estimated typical dose of about 120 mg orally.^[2] Its onset is within 30 minutes and peak effects occur after 1 hour.^[1] The effects of 2C-N have been reported to include some visual changes, similarities to MDMA, lightheadedness, eye wiggling, easier conversation, and improved mood.^[1] It was described as a "strange material, but okay".^[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

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 (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	>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
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: [6][7][8][9][10][11]

2C-N is a low-potency partial agonist of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[7][9][12]

Chemistry

Properties

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

The chemical synthesis of 2C-N has been described.^[1] It is synthesized by the mixed acid nitration of 2C-H using sulfuric acid and nitric acid.^[1]

Analogues

Analogues of 2C-N include DON, 2C-CN, and 25N-NBOMe, among others.

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)