2C-N
2C-N
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2C-N

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2C-N

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

2C-N was first synthesized by Alexander Shulgin and was described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).

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. It has an estimated typical dose of about 120 mg orally. Its onset is within 30 minutes and peak effects occur after 1 hour. The effects of 2C-N have been reported to include some visual changes, similarities to MDMA, lightheadedness, eye wiggling, easier conversation, and improved mood. It was described as a "strange material, but okay".

2C drugs like 2C-N are known to be metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B. Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs like 2C-N. This may result in overdose and serious toxicity.

2C-N is a low-potency partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.

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.

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

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

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