A δ1-opioid receptor antagonist
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BNTX (maleate)

Item No. 39829

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5α,7E)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-7-(phenylmethylene)-morphinan-6-one, 2Z-butenedioate
CAS Number
864461-31-4
Synonyms
  • 7-Benzylidenenaltrexone
Molecular Formula
C27H27NO4 • C4H4O4
Formula Weight
545.6
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
O[C@@]1(C/C2=C\C3=CC=CC=C3)[C@@]([C@@](C2=O)([H])OC4=C5O)(CC6)C4=C(C=C5)C[C@@]1([H])N6CC7CC7.OC(/C=C\C(O)=O)=O
InChi Code
InChI=1S/C27H27NO4.C4H4O4/c29-20-9-8-18-13-21-27(31)14-19(12-16-4-2-1-3-5-16)23(30)25-26(27,22(18)24(20)32-25)10-11-28(21)15-17-6-7-17;5-3(6)1-2-4(7)8/h1-5,8-9,12,17,21,25,29,31H,6-7,10-11,13-15H2;1-2H,(H,5,6)(H,7,8)/b19-12+;2-1-/t21-,25+,26+,27-;/m1./s1
InChi Key
GKHUUKGUNNYVGB-LQDKARLYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    BNTX is a δ1-opioid receptor antagonist (Ki = 0.1 nM).1 It is selective for the δ1-opioid receptor over the δ2-, μ-, and κ-opioid receptors (Kis = 10.8, 13.3, and 58.6 nM, respectively). BNTX (1 and 10 µM) decreases proliferation of primary mouse splenic B cells and the production of IL-2 and IL-4 by primary mouse splenic T lymphocytes.2 It has antinociceptive activity in the tail-flick test in mice (ED50 = 46.4 pmol/animal) and decreases the antinociceptive activity of the δ1-opioid receptor agonist DPDPE (Item No. 23184) when administered at a dose of 6.3 pmol/animal.1 BNTX (0.3-3 mg/kg) decreases the number of coughs induced by the terpene alkaloid capsaicin (Item No. 92350) in mice.3 It also reduces the number of parasitized red blood cells in a mouse model of chloroquine-resistant P. chabaudi infection when administered at a dose of 10 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Portoghese, P.S., Sultana, M., Nagase, H., et al. A highly selective δ1-opioid receptor antagonist: 7-benzylidenenaltrexone. Eur. J. Pharmacol. 218(1), 195-196 (1992).

    2. House, R.V., Thomas, P.T., Kozak, J.T., et al. Suppression of immune function by non-peptidic delta opioid receptor antagonists. Neurosci. Lett. 198(2), 119-122 (1995).

    3. Kamei, J., Iwamoto, Y., Suzuki, T., et al. Involvement of δ1-opioid receptor antagonism in the antitussive effect of δ-opioid receptor antagonists. Eur. J. Pharmacol. 251(2-3), 291-194 (1994).

    4. Miyata, Y., Fujii, H., Osa, Y., et al. Opioid δ₁ receptor antagonist 7-benzylidenenaltrexone as an effective resistance reverser for chloroquine-resistant Plasmodium chabaudi. Biooorg. Med. Chem. Lett. 21(16), 4710-4712 (2011).