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25CN-NBOMe

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25CN-NBOMe
BERJAYA
BERJAYA
Clinical data
Other names2C-CN-NBOMe; NBOMe-2C-CN
Drug classSerotonin 5-HT2 receptor agonist
Identifiers
  • 2,5-Dimethoxy-4-(2-(2-methoxybenzylamino)ethyl)benzonitrile
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC19H22N2O3
Molar mass326.396 g·mol−1
3D model (JSmol)
  • N#CC1=CC(OC)=C(CCNCC2=C(OC)C=CC=C2)C=C1OC
  • InChI=1S/C19H22N2O3/c1-22-17-7-5-4-6-15(17)13-21-9-8-14-10-19(24-3)16(12-20)11-18(14)23-2/h4-7,10-11,21H,8-9,13H2,1-3H3 checkY
  • Key:QBJWOIWLBRLGKZ-UHFFFAOYSA-N checkY

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

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Pharmacology

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Pharmacodynamics

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25CN-NBOMe activities
TargetAffinity (Ki, nM)
5-HT1AND
5-HT1BND
5-HT1DND
5-HT1END
5-HT1FND
5-HT2A1.8–4.6 (Ki)
0.40–6.7 (EC50Tooltip half-maximal effective concentration)
77–148% (EmaxTooltip maximal efficacy)
5-HT2B21–47 (Ki)
12 (EC50)
79% (Emax)
5-HT2C8–180 (Ki)
9.3–230 (EC50)
91–101% (Emax)
5-HT3ND
5-HT4ND
5-HT5AND
5-HT6145
5-HT7ND
α1A–α1DND
α2A–α2CND
β1–β3ND
D1–D5ND
H1–H4ND
M1–M5ND
I1ND
σ1, σ2ND
ORsND
TAAR1Tooltip Trace amine-associated receptor 1ND
SERTTooltip Serotonin transporterND (Ki)
ND (IC50Tooltip half-maximal inhibitory concentration)
ND (EC50)
NETTooltip Norepinephrine transporterND (Ki)
ND (IC50)
ND (EC50)
DATTooltip Dopamine transporterND (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

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

Society and culture

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Canada

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

United Kingdom

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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

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References

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  1. 1 2 3 4 5 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. 1 2 3 4 Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, et al. (19 March 2014). "Synthesis and Structure–Activity Relationships of N -Benzyl Phenethylamines as 5-HT 2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–249. doi:10.1021/cn400216u. ISSN 1948-7193. PMC 3963123. PMID 24397362.
  3. 1 2 3 4 Jensen AA, McCorvy JD, Leth-Petersen S, Bundgaard C, Liebscher G, Kenakin TP, et al. (June 2017). "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. doi:10.1124/jpet.117.239905. PMID 28360333.
  4. 1 2 3 4 Poulie CB, Pottie E, Simon IA, Harpsøe K, D'Andrea L, Komarov IV, et al. (September 2022). "Discovery of β-Arrestin-Biased 25CN-NBOH-Derived 5-HT2A Receptor Agonists". Journal of Medicinal Chemistry. 65 (18): 12031–12043. doi:10.1021/acs.jmedchem.2c00702. PMC 9511481. PMID 36099411.
  5. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  6. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
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