A Certified Reference Material
Features
  • This product is qualified as a Certified Reference Material (CRM) that has been manufactured and tested to meet ISO/IEC 17025 and ISO 17034 international standards
  • This CRM has been characterized by metrologically valid procedures and may be used as a quantitative analytical reference standard
  • Certificate of analysis provides the certified property values and the associated uncertainties, including a statement of metrological traceability for the certified values
  • Bulk material is available for qualified institutions; please contact our sales department for pricing
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6β-Naltrexol (CRM)

A 1 mg/ml solution in methanol

Item No. 18790

Safety Data Sheet (SDS) (PDF)
Synonyms
Synonyms
  • 6β-hydroxy Naltrexone
Technical Information
Formal Name
(5α,6β)-17-(cyclopropylmethyl)-4,5-epoxy-morphinan-3,6,14-triol
CAS Number
49625-89-0
Molecular Formula
C20H25NO4
Formula Weight
343.4
Formulation
A 1 mg/ml solution in methanol
SMILES
O[C@]12[C@]3(CCN(CC4CC4)[C@@H]2C5)[C@](OC6=C3C5=CC=C6O)([H])[C@H](O)CC1
InChi Code
InChI=1S/C20H25NO4/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/t14-,15-,18+,19+,20-/m1/s1
InChi Key
JLVNEHKORQFVQJ-PYIJOLGTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $103

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    Product Description

    6β-Naltrexol (Item No. 18790) is a certified reference material that is structurally categorized as an opioid. It is the major metabolite of naltrexone (Item Nos. ISO60192 | 15520).1 Unlike naltrexone, which acts as a µ-receptor antagonist or inverse agonist, 6β-naltrexol is a neutral opioid antagonist.2 6β-Naltrexol binds the µ-opioid receptor more potently than naloxone (Item Nos. ISO60191 | 15594) or naltrexone (Kis = 94, 420, and 265 pM, respectively) but is ~100-fold less effective at blocking morphine-modulated pain in vivo, as assessed using the mouse hot plate test.3 This product is intended for research and forensic applications.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Porter, S.J., Somogyi, A.A., and White, J.M. Kinetics and inhibition of the formation of 6β-naltrexol from naltrexone in human liver cytosol. Br. J. Clin. Pharmacol. 50(5), 465-471 (2000).

    2. Wang, D., Raehal, K.M., Bilsky, E.J., et al. Inverse agonists and neutral antagonists at μ opioid receptor (MOR): Possible role of basal receptor signaling in narcotic dependence. J. Neurochem. 77(6), 1590-1600 (2007).

    3. Porter, S.J., Somogyi, A.A., and White, J.M. In vivo and in vitro potency studies of 6β-naltrexol, the major human metabolite of naltrexone. Addict. Biol. 7(2), 219-225 (2002).