Chemistry:25CN-NBOMe

From HandWiki

25CN-NBOMe, also known as 2C-CN-NBOMe or NBOMe-2C-CN, is a derivative of the phenethylamine 2C-CN. It acts in a similar manner to related compounds such as 25I-NBOMe, which are potent agonists at the serotonin 5-HT2A receptor.[1][2][3][4]

Interactions

Pharmacology

Pharmacodynamics

25CN-NBOMe activities
Target Affinity (Ki, nM)
5-HT1A ND
5-HT1B ND
5-HT1D ND
5-HT1E ND
5-HT1F ND
5-HT2A 1.8–4.6 (Ki)
0.40–6.7 (EC50)
77–148% (Emax)
5-HT2B 21–47 (Ki)
12 (EC50)
79% (Emax)
5-HT2C 8–180 (Ki)
9.3–230 (EC50)
91–101% (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A ND
5-HT6 145
5-HT7 ND
α1A–α1D ND
α2A–α2C ND
β1–β3 ND
D1–D5 ND
H1–H4 ND
M1–M5 ND
I1 ND
σ1, σ2 ND
ORs ND
TAAR1 ND
SERT ND (Ki)
ND (IC50)
ND (EC50)
NET ND (Ki)
ND (IC50)
ND (EC50)
DAT ND (Ki)
ND (IC50)
ND (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [1][2][3][4]

25CN-NBOMe acts as a potent and selective agonist of the serotonin 5-HT2A receptor.[1][2][3][4] To a lesser extent, it also acts as an agonist of the serotonin 5-HT2B and 5-HT2C receptors.[1][2][3][4]

History

25CN-NBOMe was first described in the scientific literature by 2010.[1]

Society and culture

Canada

25CN-NBOMe is a controlled substance in Canada under phenethylamine blanket-ban language.[5]

United Kingdom

This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971.[6]


See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 Hansen M (2010-12-16). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (Ph.D. thesis). University of Copenhagen. doi:10.13140/RG.2.2.33671.14245.
  2. ↑ 2.0 2.1 2.2 2.3 "Synthesis and Structure–Activity Relationships of N -Benzyl Phenethylamines as 5-HT 2A/2C Agonists". ACS Chemical Neuroscience 5 (3): 243–249. 19 March 2014. doi:10.1021/cn400216u. ISSN 1948-7193. PMID 24397362. 
  3. ↑ 3.0 3.1 3.2 3.3 "Detailed Characterization of the In Vitro Pharmacological and Pharmacokinetic Properties of N-(2-Hydroxybenzyl)-2,5-Dimethoxy-4-Cyanophenylethylamine (25CN-NBOH), a Highly Selective and Brain-Penetrant 5-HT2A Receptor Agonist". The Journal of Pharmacology and Experimental Therapeutics 361 (3): 441–453. June 2017. doi:10.1124/jpet.117.239905. PMID 28360333. 
  4. ↑ 4.0 4.1 4.2 4.3 "Discovery of β-Arrestin-Biased 25CN-NBOH-Derived 5-HT2A Receptor Agonists". Journal of Medicinal Chemistry 65 (18): 12031–12043. September 2022. doi:10.1021/acs.jmedchem.2c00702. PMID 36099411. 
  5. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  6. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014" (in en). http://www.legislation.gov.uk/uksi/2014/1106/made. 




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