SML3390
25CN-NBOH hydrochloride
≥98% (HPLC)
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
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.21
Recommended Products
Quality Level
Assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
-10 to -25°C
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.
Caution
Hygroscopic
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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William E Fantegrossi et al.
Psychopharmacology, 232(6), 1039-1047 (2014-09-17)
2-([2-(4-cyano-2,5-dimethoxyphenyl)ethylamino]methyl)phenol (25CN-NBOH) is structurally similar to N-benzyl substituted phenethylamine hallucinogens currently emerging as drugs of abuse. 25CN-NBOH exhibits dramatic selectivity for 5-HT2A receptors in vitro, but has not been behaviorally characterized. 25CN-NBOH was compared to the traditional phenethylamine hallucinogen R(-)-2,5-dimethoxy-4-iodoamphetamine
Tobias Buchborn et al.
Frontiers in pharmacology, 9, 17-17 (2018-02-23)
The serotonin (5-HT) 2A receptor is the primary molecular target of serotonergic hallucinogens, which trigger large-scale perturbations of the cortex. Our understanding of how 5-HT2A activation may cause the effects of hallucinogens has been hampered by the receptor unselectivity of
Anna U Odland et al.
Neuropharmacology, 183, 107838-107838 (2019-11-07)
5-Hydroxytryptamine 2A receptor (5-HT2AR) agonist psychedelics are increasingly recognized as potentially useful treatments of psychiatric disorders, such as obsessive-compulsive disorder, depression, anxiety, and drug dependence. There is limited understanding of the way they exert their therapeutic action, but inhibition of
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
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
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