SML3390
25CN-NBOH hydrochloride
≥98% (HPLC), 5-HT2A receptor agonist, powder
Synonym(s):
2-([2-(4-Cyano-2, 5-dimethoxyphenyl)ethylamino]methyl)phenol hydrochloride, 4-(2-(2-Hydroxybenzylamino)ethyl)-2,5-dimethoxybenzonitrile hydrochloride, NBOH-2C-CN hydrochloride
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About This Item
Empirical Formula (Hill Notation):
C18H20N2O3·HCl
CAS Number:
Molecular Weight:
348.82
UNSPSC Code:
12352200
NACRES:
NA.21
MDL number:
Product Name
25CN-NBOH hydrochloride, ≥98% (HPLC)
assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
-10 to -25°C
Quality Level
Related Categories
Biochem/physiol Actions
25CN-NBOH is a brain-penetrant, highly potent and selective 5-HT2A receptor agonist (human 2A/rat 2C Ki = 1.3/132 nM; human 2A/2C PI turnover EC50 = 2.1/190 nM) with much reduced efficacy toward human 2B & 2C subtypes (Ki ratio: 2C/2A = 52-81 & 2B/2A = 37; Ca2+ mobilization Δlog(Rmax/EC50 ratio: 2C/2A = 30-180 & 2B/2A = 54; 2C/2A PI turnover EC50 ratio = 81-146) and other receptors/transporters/kinases. When administered in mice in vivo (1, 3, 6 mg/kg s.c.), 25CN-NBOH produces hallucinogen-like effects blockable by 5-HT2A antagonist M100907, but not 5-HT2C antagonist RS102221.
Brain-penetrant, highly potent and selective 5-HT2A receptor agonist with good in vitro & in vivo efficacy.
Disclaimer
Hygroscopic
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Martin Hansen et al.
ACS chemical neuroscience, 5(3), 243-249 (2014-01-09)
N-Benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5-dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a
Adam L Halberstadt et al.
Neuropharmacology, 107, 364-375 (2016-03-30)
Timing deficits are observed in patients with schizophrenia. Serotonergic hallucinogens can also alter the subjective experience of time. Characterizing the mechanism through which the serotonergic system regulates timing will increase our understanding of the linkage between serotonin (5-HT) and schizophrenia
Adam L Halberstadt et al.
Psychopharmacology, 236(2), 821-830 (2018-11-19)
There is evidence that mGlu2/3 receptors regulate 5-HT2A signaling, interactions that have been theorized to play a role in the antipsychotic-like effects of mGlu2/3 agonists as well as the hallucinogenic effects of 5-HT2A agonists. One approach to unraveling this interaction
Dionisio A Amodeo et al.
Behavioural brain research, 395, 112861-112861 (2020-08-20)
Serotonin 2A (5-HT2A) receptors are the primary site of action of hallucinogenic drugs and the target of atypical antipsychotics. 5-HT2A receptors are also implicated in executive function, including behavioral flexibility. Previous studies showed that 5-HT2A receptor blockade improved behavioral flexibility
Tobias Buchborn et al.
Journal of psychopharmacology (Oxford, England), 34(7), 786-794 (2020-02-13)
Serotonin 2A receptors, the molecular target of psychedelics, are expressed by neuronal and vascular cells, both of which might contribute to brain haemodynamic characteristics for the psychedelic state. Aiming for a systemic understanding of psychedelic vasoactivity, here we investigated the
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