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). 2C-N Entry in PiHKAL

Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-N's dose range as 100 to 150mg or more orally and a duration of 4 to 6hours. It has an estimated typical dose of about 120mg orally. Its onset is within 30minutes and peak effects occur after 1hour. 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".

Interactions

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.

Pharmacology Pharmacodynamics + Target Affinity (Ki, nM) 5-HT1A 1,450–2,200 5-HT1B >10,000 5-HT1D 832 5-HT1E 676 5-HT1F 5-HT2A 23.5–72.4 (Ki)32.2–170 ()48–100% () 5-HT2B 123 (Ki)730 ()74% () 5-HT2C 162–370 (Ki) () () 5-HT3 >10,000 5-HT4 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 σ1, σ2 >10,000 >10,000 >20,000 (Ki) (mouse)340 (Ki) (rat)15,000 () (mouse)250 () (rat)>10,000 () (human)28% () (mouse)59% () (rat) 32,000 (Ki)154,000 () () >30,000 (Ki)287,000 () () >30,000 (Ki)>900,000 () () () 66,000 () Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:

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

Chemistry Properties Salts of 2C-N have a bright yellow to orange color due to the presence of the nitro group, unlike all other members of the 2C family in which the salts are white.

Synthesis 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 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.

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

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.

Bron en licentie