Ignavine

Ignavine
Clinical data
Other names	3,9,15-Trihydroxyhetisan-2-yl benzoate
Drug class	μ-Opioid receptor positive allosteric modulator or agonist; Analgesic
Identifiers
	IUPAC name [(3R,4R,5R,11S,13R,16R,17R,18R)-4,13,18-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-3-yl] benzoate;
CAS Number	1357-76-2;
PubChem CID	3035320;
ChemSpider	2299598;
ChEBI	CHEBI:138829;
Chemical and physical data
Formula	C27H31NO5
Molar mass	449.547 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CN3[C@H]4[C@H]1C5(C3C6C[C@H]7C[C@@]5(C6(C4)[C@@H](C7=C)O)O)C[C@H]([C@@H]2O)OC(=O)C8=CC=CC=C8;
	InChI InChI=1S/C27H31NO5/c1-13-15-8-16-20-26-11-18(33-23(31)14-6-4-3-5-7-14)22(30)24(2)12-28(20)17(19(24)26)10-25(16,21(13)29)27(26,32)9-15/h3-7,15-22,29-30,32H,1,8-12H2,2H3/t15-,16?,17+,18+,19+,20?,21+,22-,24-,25?,26?,27-/m0/s1; Key:FOIZZXKAYVIZQC-HBFXMWHYSA-N;

Ignavine is a naturally occurring diterpene alkaloid found in Aconiti tuber.^[1]^[2]^[3]^[4]^[5] It has been reported to act as a μ-opioid receptor (MOR) positive allosteric modulator (PAM).^[1]^[3]^[4]^[6] The drug potentiated responses to the selective MOR agonist DAMGO at low concentrations but inhibited DAMGO at high concentrations.^[1]^[4]^[6] Ignavine alone has been found to produce analgesic effects in animals, but with a biphasic dose–response curve.^[4]^[1] Although described as a MOR PAM, other research suggests that ignavine is a ligand of the orthosteric site of the MOR and does not act as a PAM.^[1] Instead, it may be a MOR partial agonist.^[1] However, more research is necessary to clarify its MOR actions.^[1] Ignavine was first isolated by 1952^[5] and its reported MOR PAM activity was first reported by 2016.^[2]^[6]

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