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SML3390

Sigma-Aldrich

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:
1539266-32-4
Molecular Weight:
348.82
MDL number:
MFCD28133404
UNSPSC Code:
12352200
NACRES:
NA.21

Quality Level

100

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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.
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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