A 5-HT1B receptor antagonist
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NAS-181

Item No. 39191

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R)-2-[[[3-(4-morpholinylmethyl)-2H-1-benzopyran-8-yl]oxy]methyl]-morpholine, bimethanesulfonate
CAS Number
1217474-40-2
Molecular Formula
C19H26N2O4 • 2CH3SO3H
Formula Weight
538.6
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: SolubleDMSO: SolubleMethanol: SolubleWater: Soluble
SMILES
CS(=O)(O)=O.CS(=O)(O)=O.N1(CC2=CC3=CC=CC(OC[C@@H]4OCCNC4)=C3OC2)CCOCC1
InChi Code
InChI=1S/C19H26N2O4.2CH4O3S/c1-2-16-10-15(12-21-5-8-22-9-6-21)13-25-19(16)18(3-1)24-14-17-11-20-4-7-23-17;2*1-5(2,3)4/h1-3,10,17,20H,4-9,11-14H2;2*1H3,(H,2,3,4)/t17-;;/m1../s1
InChi Key
WMRMIRRDPBKNMY-ZEECNFPPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $76

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    5 mg

    $343

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    10 mg

    $646

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    Product Description

    NAS-181 is an antagonist of the serotonin (5-HT) receptor subtype 5-HT1B (Ki = 47 nM for the rat receptor).1 It is selective for 5-HT1B over 5-HT1A, 5-HT2A, 5-HT2C, 5-HT6, and 5-HT7 (Kis = >3,000 nM for all for the rat receptors). NAS-181 (100 or 1,000 nM) potentiates potassium-stimulated 5-HT release in isolated and preloaded rat occipital cortical slices. It increases extracellular levels of acetylcholine (ACh), but not glutamate or GABA, in the frontal cortex and ventral hippocampus of non-anesthetized rats when administered at doses of 1, 5, or 10 mg/kg.2 NAS-181 (3 mg/kg) induces wet-dog shakes in rats, an effect that can be prevented by the tryptophan hydroxylase inhibitor p-chloro phenylalanine (Item No. 26168).1 It increases the length of freezing time induced by contextual fear conditioning in mice.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Berg, S., Larsson, L.G., Rényi, L., et al. (R)-(+)-2-[[[3-(Morpholinomethyl)-2H-chromen-8-yl]oxy]methyl] morpholine methanesulfonate: A new selective rat 5-hydroxytryptamine1B receptor antagonist. J. Med. Chem. 41(11), 1934-1942 (1998).

    2. Hu, X.J., Wang, F.-H., Stenfors, C., et al. Effects of the 5-HT1B receptor antagonist NAS-181 on extracellular levels of acetylcholine, glutamate and GABA in the frontal cortex and ventral hippocampus of awake rats: A microdialysis study. Eur. Neuropsychopharmacol. 17(9), 580-586 (2007).

    3. Hessel, M., Pape, H.-C., and Seidenbecher, T. Stimulation of 5-HT receptors in anterodorsal BNST guides fear to predictable and unpredictable threat. Eur. Neuropsychopharmacol. 39, 56-69 (2020).