9-Oxaergoline

9-Oxaergoline is a low-potency dopamine receptor agonist related to the ergolines.^[1][2][3] It is the analogue and bioisostere of ergoline in which the carbon atom at the 9 position of the ergoline ring system has been replaced with an oxygen atom.^[1][2][3] A few notable derivatives of 9-oxaergoline have been studied and characterized, including RU-29717 (N-propyl-9-oxaergoline), 6-ethyl-9-oxaergoline (EOE), and voxergolide (RU-41656), which are all substantially more potent as dopamine receptor agonists than 9-oxaergoline itself.^[3][4] Other derivatives, such as N-methyl-9-oxaergoline, have been characterized as well.^[3] In addition to its dopaminergic activity, RU-29717 is notable in also having affinity for serotonin receptors and in producing a short-lasting head-twitch response in rodents.^[5][6] The head-twitch response is notable in being a behavioral proxy of psychedelic effects caused by serotonin 5-HT_2A receptor agonism.^[7][8] The potential serotonergic activities of 9-oxaergoline and N-methyl-9-oxaergoline do not appear to have been reported.^{[1][2][3][5][6]}

Other names(6aR,10aR)-4,6a,7,8,9,10a-hexahydro-6H-indolo[3,4-gh][1,4]benzoxazine

Drug classDopamine receptor agonist

ATC code

• None

PubChem CID

• 22813385

Quick facts Clinical data, Other names ...

9-Oxaergoline

Clinical data
Other names	(6aR,10aR)-4,6a,7,8,9,10a-hexahydro-6H-indolo[3,4-gh][1,4]benzoxazine
Drug class	Dopamine receptor agonist
ATC code	None
Identifiers
IUPAC name (2R,7R)-3-oxa-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraene
PubChem CID	22813385
ChemSpider	18531393
ChEMBL	ChEMBL121653
Chemical and physical data
Formula	C13H14N2O
Molar mass	214.268 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CO[C@H]2[C@H](N1)CC3=CNC4=CC=CC2=C34
InChI InChI=1S/C13H14N2O/c1-2-9-12-8(7-15-10(12)3-1)6-11-13(9)16-5-4-14-11/h1-3,7,11,13-15H,4-6H2/t11-,13-/m1/s1 Key:VHGCBDMLWAGBAP-DGCLKSJQSA-N

Close