2C-N

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2C-N, also known as 4-nitro-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.<ref name="PiHKAL" /> It is taken orally.<ref name="PiHKAL" />

2C-N was first synthesized by Alexander Shulgin and was described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).<ref name="PiHKAL">Template:CitePiHKAL 2C-N Entry in PiHKAL</ref>

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-N's dose range as 100 to 150Template:Nbspmg or more orally and a duration of 4 to 6Template:Nbsphours.<ref name="PiHKAL" /><ref name="LuethiLiechti2018">Template:Cite journal</ref> It has an estimated typical dose of about 120Template:Nbspmg orally.<ref name="LuethiLiechti2018" /> Its onset is within 30Template:Nbspminutes and peak effects occur after 1Template:Nbsphour.<ref name="PiHKAL" /> The effects of 2C-N have been reported to include some visual changes, similarities to MDMA, lightheadedness, eye wiggling, easier conversation, and improved mood.<ref name="PiHKAL" /> It was described as a "strange material, but okay".<ref name="PiHKAL" />

Interactions

Template:See also

2C drugs like 2C-N are known to be metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.<ref name="DeanStellpflugBurnett2013">Template:Cite journal</ref><ref name="TheobaldMaurer2007">Template:Cite journal</ref> Monoamine oxidase inhibitors (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">Template:Cite journal</ref> This may result in overdose and serious toxicity.<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" />

Pharmacology

Pharmacodynamics

Template:Nowrap
Target Affinity (Ki, nM)
5-HT1A 1,450–2,200
5-HT1B >10,000
5-HT1D 832
5-HT1E 676
5-HT1F Template:Abbr
5-HT2A 23.5–72.4 (Ki)
170 (Template:Abbrlink)
48% (Template:Abbrlink)
5-HT2B 123 (Ki)
730 (Template:Abbr)
74% (Template:Abbr)
5-HT2C 162–370 (Ki)
Template:Abbr (Template:Abbr)
Template:Abbr (Template:Abbr)
5-HT3 >10,000
5-HT4 Template:Abbr
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 Template:Abbr
σ1, σ2 >10,000
[[Opioid receptor|Template:Abbr]] >10,000
Template:Abbrlink >20,000 (Ki) (mouse)
340 (Ki) (rat)
15,000 (Template:Abbr) (mouse)
250 (Template:Abbr) (rat)
>10,000 (Template:Abbr) (human)
28% (Template:Abbr) (mouse)
59% (Template:Abbr) (rat)
Template:Abbrlink 32,000 (Ki)
154,000 (Template:Abbrlink)
Template:Abbr (Template:Abbr)
Template:Abbrlink >30,000 (Ki)
287,000 (Template:Abbr)
Template:Abbr (Template:Abbr)
Template:Abbrlink >30,000 (Ki)
>900,000 (Template:Abbr)
Template:Abbr (Template:Abbr)
Template:Abbrlink Template:Abbr (Template:Abbr)
Template:Abbrlink 66,000 (Template:Abbr)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: <ref name="PDSPKiDatabase">Template:Cite web</ref><ref name="RickliLuethiReinisch2015">Template:Cite journal</ref><ref name="WallachCaoCalkins2023">Template:Cite journal</ref><ref name="MoyaBergGutiérrez-Hernandez2007">Template:Cite journal</ref><ref name="WagmannBrandtStratford2019">Template:Cite journal</ref><ref name="SimmlerBuchyChaboz2016">Template:Cite journal</ref>

2C-N is a low-potency partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.<ref name="RickliLuethiReinisch2015">Template:Cite journal</ref><ref name="MoyaBergGutiérrez-Hernandez2007" /><ref name="Acuña-CastilloVillalobosMoya2002">Template:Cite journal</ref>

Chemistry

Properties

Salts of 2C-N have a bright yellow to orange color due to the presence of the nitro group,Template: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.<ref name="PiHKAL" /> It is synthesized by the mixed acid nitration of 2C-H using sulfuric acid and nitric acid.<ref name="PiHKAL" />

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.<ref name="PiHKAL" />

Society and culture

Canada

As of October 31, 2016, 2C-N is a controlled substance (Schedule III) in Canada.<ref>Template:Cite web</ref>

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.<ref>Template:Cite web</ref>

See also

References

Template:Reflist

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