2C-N
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| _other_data=2-(2,5-dimethoxy-4-nitrophenyl)ethan-1-amine
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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.<ref name="PiHKAL">Template:CitePiHKAL 2C-N Entry in PiHKAL</ref>
UseEdit
Shulgin, in his book PiHKAL, as well as other sources, list the dosage range as 100 to 150Template:Nbspmg or more, with a typical dose estimate of about 120Template:Nbspmg.<ref name="PiHKAL"/><ref name="LuethiLiechti2018">Template:Cite journal</ref> 2C-N is generally taken orally, and effects typically last 4 to 6Template:Nbsphours.<ref name="PiHKAL"/>
EffectsEdit
Shulgin accounts his experiences after ingesting 2C-N:<ref name="PiHKAL" />
(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.
PharmacologyEdit
| 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 | Template:Abbr | |
| α2A | 1,300 | |
| α2B, α2C | Template:Abbr | |
| β1–β3 | Template:Abbr | |
| D1 | 19,000 | |
| D2 | 6,100 | |
| D3 | 20,000 | |
| D4, D5 | Template:Abbr | |
| H1 | >25,000 | |
| H2–H4 | Template:Abbr | |
| M1–M5 | Template:Abbr | |
| I1 | Template:Abbr | |
| σ1, σ2 | Template:Abbr | |
| 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">{{#invoke:citation/CS1|citation | CitationClass=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>
ChemistryEdit
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,Template:Citation needed unlike all other members of the 2C family in which the salts are white.
SynthesisEdit
2C-N is synthesized by the mixed acid nitration of 2C-H using sulfuric acid and nitric acid.<ref name="PiHKAL"/>
Society and cultureEdit
Legal statusEdit
CanadaEdit
As of October 31, 2016, 2C-N is a controlled substance (Schedule III) in Canada.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
United KingdomEdit
2C-N and most (possibly all) other compounds featured in PiHKAL are illegal drugs in the United Kingdom.
United StatesEdit
In the United States, 2C-N is a Schedule 1 controlled substance.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
See alsoEdit
ReferencesEdit
Template:Psychedelics Template:Serotonin receptor modulators Template:TAAR modulators {{#invoke:Navbox|navbox}}