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N9412

6β-Naltrexol hydrate

Name: 6β-Naltrexol hydrate
Brand: SIGMA

≥96% (HPLC), powder

Synonym(s):

(5α,6β)-17-(Cyclopropylmethyl)-4,5-epoxy-morphinan-3,6,14-triol hydrate

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₂₅NO₄ · xH₂O

CAS Number:

1034528-53-4

Molecular Weight:

343.42 (anhydrous basis)

MDL number:

MFCD08277038

UNSPSC Code:

12352200

PubChem Substance ID:

24724560

NACRES:

NA.77

Quality Level

100

assay

≥96% (HPLC)

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

color

white

solubility

DMSO: ~12 mg/mL
H₂O: insoluble

storage temp.

2-8°C

SMILES string

[H]O[H].O[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5O[C@@H]1[C@]2(CCN3CC6CC6)c45

InChI

1S/C20H25NO4.H2O/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11;/h3-4,11,14-15,18,22-24H,1-2,5-10H2;1H2/t14-,15-,18+,19+,20-;/m1./s1

InChI key

VHGGWFVHXKTOPK-CDHBEYIESA-N

Biochem/physiol Actions

Neutral antagonist of the μ-opioid receptor. A reduction of withdrawal effects associated with neutral μ-opioid receptor antagonists may offer advantages in treating opioid overdose and addiction.

Features and Benefits

This compound is featured on the Opioid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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In vivo characterization of 6beta-naltrexol, an opioid ligand with less inverse agonist activity compared with naltrexone and naloxone in opioid-dependent mice.

Kirsten M Raehal et al.

The Journal of pharmacology and experimental therapeutics, 313(3), 1150-1162 (2005-02-18)

The mu-opioid receptor displays basal signaling activity, which seems to be enhanced by exposure to opioid agonists. This study assesses the in vivo pharmacology of the putative "neutral" antagonist 6beta-naltrexol in comparison to other ligands with varying efficacy, such as

Articles

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