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Oxa-noribogaine

Oxa-noribogaine
Clinical data
Other namesOxanoribogaine
Drug classAtypical κ-opioid receptor partial agonist
Identifiers
  • (1R,15S,17S)-17-ethyl-3-oxa-13-azapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraen-7-ol
PubChem CID
Chemical and physical data
FormulaC19H23NO2
Molar mass297.398 g·mol−1
3D model (JSmol)
  • CC[C@H]1C[C@H]2C[C@@H]3C1N(C2)CCC4=C3OC5=C4C=C(C=C5)O
  • InChI=InChI=1S/C19H23NO2/c1-2-12-7-11-8-16-18(12)20(10-11)6-5-14-15-9-13(21)3-4-17(15)22-19(14)16/h3-4,9,11-12,16,18,21H,2,5-8,10H2,1H3/t11-,12-,16+,18?/m0/s1
  • Key:FZMCHQSKCBWMJA-UPHWXITMSA-N

Oxa-noribogaine is an atypical κ-opioid receptor agonist of the "oxa-iboga" family and a synthetic benzofuran analogue of noribogaine.[1][2][3] Although it still binds to hERG with similar avidity as noribogaine, it appears to be devoid of the proarrhythmic side effects of noribogaine.[1][3]

The drug has analgesic effects as a potent atypical κ-opioid receptor partial agonist and, opposed to typical κ-opioid receptor agonists, is characterized by the absence of pro-depressant effects.[1][3] It induces a robust κ-opioid receptor-dependent increase in GDNF protein levels in the ventral tegmental area and medial prefrontal cortex.[1][3] After a single dose or short-term treatment, oxa-noribogaine induces long-lasting suppression of opioid drug-seeking behavior in rodent relapse models.[1][3] It also counteracts persistent opioid-induced hyperalgesia.[3]

Oxa-noribogaine was first described in the literature in 2015 and was then further described in 2024.[1][4][2][3]

See also

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References

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  1. ^ a b c d e f Liu-Chen LY, Huang P (2025). "KOR agonists for the treatment and/or prevention of opioid use disorder and cocaine use disorder". Pharmacology Biochemistry and Behavior. 254 174056. doi:10.1016/j.pbb.2025.174056. PMID 40588011. Retrieved 31 July 2025.
  2. ^ a b Obeng S, McMahon LR, Ofori E (February 2025). "Patent review of novel compounds targeting opioid use disorder (2018-2024)". Expert Opinion on Therapeutic Patents. 35 (2): 165–180. doi:10.1080/13543776.2024.2446230. PMID 39816001.
  3. ^ a b c d e f g Havel V, Kruegel AC, Bechand B, McIntosh S, Stallings L, Hodges A, et al. (2024). "Oxa-Iboga alkaloids lack cardiac risk and disrupt opioid use in animal models". Nature Communications. 15 (1) 8118. Bibcode:2024NatCo..15.8118H. doi:10.1038/s41467-024-51856-y. PMC 11415492. PMID 39304653.
  4. ^ Hughes AJ, Hamelink CR, Townsend SD (5 September 2024). "Disrupting Substance Use Disorder: The Chemistry of Iboga Alkaloids". European Journal of Organic Chemistry e202400432. doi:10.1002/ejoc.202400432. ISSN 1434-193X.



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