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Submit ReviewNBOH-2C-CN hydrochloride
Description: High affinity and selective 5-HT2A agonist
Alternative Names: 25CN-NBOH
Chemical Name: 4-[2-[[(2-Hydroxyphenyl)methyl]amino]ethyl]-2,5-dimethoxybenzonitrile hydrochloride
Purity: ≥98% (HPLC)
Biological Activity for NBOH-2C-CN hydrochloride
NBOH-2C-CN hydrochloride is a high affinity, selective 5-HT2A agonist (Ki = 1.3 nM). Exhibits 100-fold selectivity for 5-HT2A over 5-HT2C. Elicits head twitch behavior in mice.
Technical Data for NBOH-2C-CN hydrochloride
| M. Wt | 348.82 |
| Formula | C18H20N2O3.HCl |
| Storage | Desiccate at RT |
| Purity | ≥98% (HPLC) |
| CAS Number | 1539266-32-4 |
| PubChem ID | 90489019 |
| InChI Key | JQVAEIIIMVMJBO-UHFFFAOYSA-N |
| Smiles | OC(C=CC=C2)=C2CNCCC1=C(OC)C=C(C#N)C(OC)=C1.Cl |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for NBOH-2C-CN hydrochloride
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 3.49 | 10 with gentle warming | |
| DMSO | 34.88 | 100 |
Preparing Stock Solutions for NBOH-2C-CN hydrochloride
The following data is based on the product molecular weight 348.82. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.87 mL | 14.33 mL | 28.67 mL |
| 5 mM | 0.57 mL | 2.87 mL | 5.73 mL |
| 10 mM | 0.29 mL | 1.43 mL | 2.87 mL |
| 50 mM | 0.06 mL | 0.29 mL | 0.57 mL |
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Product Datasheets for NBOH-2C-CN hydrochloride
References for NBOH-2C-CN hydrochloride
References are publications that support the biological activity of the product.
Hansen et al (2014) Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS.Chem.Neurosci. 5 243 PMID: 24397362
Fantegrossi et al (2014) Hallucinogen-like effects of 2-([2-(4-cyano-2,5-dimethoxyphenyl) ethylamino]methyl)phenol (25CN-NBOH), a novel N-benzylphenethylamine with 100-fold selectivity for 5-HT2A receptors, in mice. Psychopharmacology (Berl.) 232 1039 PMID: 25224567
Jensen et al (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. J.Pharmacol.Exp.Ther 361 441 PMID: 28360333
Jensen et al (2020) The selective 5-HT2A receptor agonist 25CN-NBOH: Structure-activity relationship, in vivo pharmacology, and in vitro and ex vivo binding characteristics of [ 3H]25CN-NBOH. Biochem.Pharmacol. 177 113979 PMID: 32298690
If you know of a relevant reference for NBOH-2C-CN hydrochloride, please let us know.
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2 Citations for NBOH-2C-CN hydrochloride
Citations are publications that use Tocris products. Selected citations for NBOH-2C-CN hydrochloride include:
Hongyan et al (2022) Bimodal modulation of short-term motor memory via dynamic sodium pumps in a vertebrate spinal cord. Curr Biol 32 1038-1048.e2 PMID: 35104440
Wieland B et al (2020) Serotonin Receptor 2A Activation Promotes Evolutionarily Relevant Basal Progenitor Proliferation in the Developing Neocortex. Neuron 108 1113-1129.e6 PMID: 33080227
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Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
*Please note that Tocris will only send literature to established scientific business / institute addresses.
5-HT Receptors Scientific Review
Written by Nicholas M. Barnes and John F. Neumaier, this review summarizes the various serotonin receptor subtypes and their importance in mediating the role of serotonin in numerous physiological and pharmacological processes. Compounds available from Tocris are listed.
Depression Poster
Major depressive disorder is characterized by depressed mood and a loss of interest and/or pleasure. Updated in 2015 this poster highlights presynaptic and postsynaptic targets for the potential treatment of major depressive disorder, as well as outlining the pharmacology of currently approved antidepressant drugs.
Parkinson's Disease Poster
Parkinson's disease (PD) causes chronic disability and is the second most common neurodegenerative condition. This poster outlines the neurobiology of the disease, as well as highlighting current therapeutic treatments for symptomatic PD, and emerging therapeutic strategies to delay PD onset and progression.