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Merck
CN

SML3632

Sigma-Aldrich

NAQ

≥98% (HPLC)

Synonym(s):

17-Cyclopropylmethyl-3,14b-dihydroxy-4,5a-epoxy-6a-[(3’-isoquinolyl)acetamido]morphinan dihydrochloride, N-[(5α,6α)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl]-3-isoquinolinecarboxamide dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C30H31N3O4·2HCl
CAS Number:
Molecular Weight:
570.51
UNSPSC Code:
12352116
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Quality Level

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O[C@]12[C@@]34C5=C(C[C@H]2N(CC4)CC6CC6)C=CC(O)=C5O[C@@]3([H])[C@H](CC1)NC(C7=CC8=C(C=CC=C8)C=N7)=O.[2HCl]

Biochem/physiol Actions

Highly selective and high-affinity mu (μ) opioid receptor (MOR) antagonist in vitro and in vivo.




NAQ is a highly selective and high-affinity mu (μ) opioid receptor (MOR) antagonist with 241- & 48-fold selectivity over the delta (δ) and kappa (κ) opioid receptor, respectively (MOR/DOR/KOR Ki = 0.55/132.5/26.45 nM) and little MOR agonist activity (Emax = 15.83% of that of DAMGO by GTP[γS] binding using membrane from MOR-expressing cells). NAQ effectively antagonizes morphine antinociceptive effects in mice in vivo (warm-water tail immersion test AD50 = 0.45 mg/kg s.c. 5 min prior to 10 mg morphine/kg s.c.; no agonist efficacy up to 100 mg/kg).

Disclaimer

Hygroscopic

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Kathryn L Schwienteck et al.
Neuropharmacology, 150, 200-209 (2019-01-21)
One emerging strategy to address the opioid crisis is the development of mu opioid receptor (MOR) ligands that preferentially signal the G-protein vs. β-arrestin pathway. The present study compared the relative potency and effectiveness of two G-protein biased (GPB)-MOR ligands
Yunyun Yuan et al.
Bioorganic & medicinal chemistry letters, 23(18), 5045-5048 (2013-08-21)
17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(isoquinoline-3'-carboxamido)morphinan (NAQ) was previously designed following the 'message-address' concept and was identified as a potent and highly selective mu opioid receptor (MOR) ligand based on its pharmacological profile. We here report the preliminary structure activity relationship (SAR) studies of this
Guo Li et al.
Journal of medicinal chemistry, 52(5), 1416-1427 (2009-02-10)
Opioid receptor selective antagonists are important pharmacological probes in opioid receptor structural characterization and opioid agonist functional study. Thus far, a nonpeptidyl, highly selective and reversible mu opioid receptor (MOR) antagonist is unavailable. On the basis of our modeling studies
Jeremy C Cornelissen et al.
European journal of pharmacology, 844, 175-182 (2018-12-16)
Mu-opioid receptor agonists are clinically effective analgesics, but also produce undesirable effects that limit their clinical utility. The nociceptin opioid peptide (NOP) receptor system also modulates nociception, and NOP agonists might be useful adjuncts to enhance the analgesic effects or
Samuel Obeng et al.
European journal of pharmacology, 827, 32-40 (2018-03-14)
Evidence has shown that downstream signaling by mu opioid receptor (MOR) agonists that recruit β-arrestin2 may lead to the development of tolerance. Also, it has been suggested that opioid receptor desensitization and cyclic AMP overshoot contributes to the development of

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