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Merck
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Principaux documents

SML3390

Sigma-Aldrich

25CN-NBOH hydrochloride

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C18H20N2O3·HCl
Numéro CAS:
Poids moléculaire :
348.82
Numéro MDL:
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.21

Niveau de qualité

Essai

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

-10 to -25°C

Actions biochimiques/physiologiques

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.

Attention

Hygroscopic

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

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
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
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

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