Oxa-noribogaine

Oxa-noribogaine
Clinical data
Other names	Oxanoribogaine
Drug class	Atypical κ-opioid receptor partial agonist
Identifiers
	IUPAC name (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	171470286;
Chemical and physical data
Formula	C19H23NO2
Molar mass	297.398 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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. Although it still binds to hERG with similar avidity as noribogaine, it appears to be devoid of the proarrhythmic side effects of noribogaine.

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. It induces a robust κ-opioid receptor-dependent increase in GDNF protein levels in the ventral tegmental area and medial prefrontal cortex. After a single dose or short-term treatment, oxa-noribogaine induces long-lasting suppression of opioid drug-seeking behavior in rodent relapse models. It also counteracts persistent opioid-induced hyperalgesia.

Oxa-noribogaine was first described in the literature in 2015, and was then further described in 2024.