2C-N (2,5-dimethoxy-4-nitrophenethylamine) is a

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science o ...

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace am ...

of the

2C family 2C (2C-''x'') is a general name for the family of psychedelic drug, psychedelic phenethylamines containing Methoxy, methoxy groups on the 2 and 5 carbon, positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the ...

. It was first synthesized by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymetha ...

.2C-N Entry in ''PiHKAL''
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Chemistry

The full name of the chemical is 2-(2,5-di

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

-4-

nitro Nitro may refer to: Chemistry *Nitrogen, a chemical element and a gas except at very low temperatures, with which many compounds are formed: **Nitro compound, an organic compound containing one or more nitro functional groups, -NO2 **Nitroalkene, ...

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen ...

)ethanamine.

Salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively c ...

of 2C-N have a bright yellow to orange color due to the presence of the

group, 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 2C-H (2,5-dimethoxyphenethylamine) is a lesser-known substituted phenethylamine of the 2C family. History 2C-H was first synthesized in 1932 by Johannes S. Buck. Use 2C-H is used as a precursor in the synthesis of other substituted phenethyla ...

using

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular fo ...

and

nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available ni ...

Dosage

In his book '' PiHKAL'', Shulgin lists the dosage range as 100-150 mg. 2C-N is generally taken orally, and effects typically last 4 to 6 hours.

Effects

Shulgin accounts his experiences after ingesting 2C-N:

(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.

Legal status

Canada

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

United States

In the United States, 2C-N is a Schedule 1 controlled substance.

United Kingdom

2C-N and most (possibly all) other compounds featured in PiHKAL are illegal drugs in the United Kingdom.

References

{{2Cs 2C (psychedelics) Nitrobenzenes