2-Hydroxy-11-(2-methylallyl)oxynoraporphine

vanc 6 2-Hydroxy-11-(2-methylallyl)oxynoraporphine.svg skin-invert-image 200px Serotonin 5-HT2A receptor agonist; Serotonin 5-HT2C receptor agonist None 175794278 "Compound 20s"; "Compound S30" 11-(2-methylprop-2-enoxy)-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol 20 21 1 2 CC(=C)COC1=CC=CC2=C1C3=CC(=CC4=C3C(C2)NCC4)O 1S/C20H21NO2/c1-12(2)11-23-18-5-3-4-13-9-17-19-14(6-7-21-17)8-15(22)10-16(19)20(13)18/h3-5,8,10,17,21-22H,1,6-7,9,11H2,2H3 QBPVUNKTSFWCKO-UHFFFAOYSA-N 2-Hydroxy-11-(2-methylallyl)oxynoraporphine is a serotonin 5-HT2A and 5-HT2C receptor agonist of the noraporphine family. Qin W, Zhang B, Wang Q, Jiang G, Cui J, Chen F, Wang L, Chen J, Tian S, Zhen XC, Shui W, Ye N November 2025 Discovery of New N-H Aporphine Derivatives As Brain-Penetrant Gq-Biased 5-HT2C Receptor Agonists and Dual 5-HT2C/5-HT2A Receptor Agonists Journal of Medicinal Chemistry 68 21 23300–23323 10.1021/acs.jmedchem.5c02115 41108743 Notably, the (2-methylallyl)oxy analogue 20s exhibited the highest potency at 5-HT2AR (EC50 = 6.3 nM, Emax = 82%) in this report, while displaying comparable potency at 5-HT2CR (EC50 = 8.0 nM, Emax = 95%). CN 115108986A Aporphine derivative and preparation method and application thereof 27 September 2022 https://patents.google.com/patent/CN115108986A/en Ye N, Shui W, Qin W, Zhang B, Jiang G Suzhou University ShanghaiTech University It is a synthetic compound and is an analogue of aporphine alkaloids like nuciferine, but shows agonism rather than antagonism of serotonin 5-HT2 receptors. It is a potent full agonist or high-efficacy partial agonist of the serotonin 5-HT2A and 5-HT2C receptors. The drug's EC50 half-maximal effective concentration (Emax maximal efficacy) values were 6.3 to 9.4nM (83–84%) at the serotonin 5-HT2A receptor and 8.0 to 9.8nM (95–103%) at the serotonin 5-HT2C receptor. It showed no agonistic activity at the serotonin 5-HT2B receptor at concentrations of up to 30,000nM. 2-Hydroxy-11-(2-methylallyl)oxynoraporphine was among the most potent serotonin 5-HT2A receptor agonists of a large series of assessed noraporphines. The chemical synthesis of 2-hydroxy-11-(2-methylallyl)oxynoraporphine has been described. A variety of analogues of the drug with similar activity have also been described. 2-Hydroxy-11-(2-methylallyl)oxynoraporphine was first described in the scientific literature by Wangzhi Qin and colleagues in 2025. It had previously been patented in 2022. See also List of miscellaneous serotonin 5-HT2A receptor agonists Aporphine alkaloids 11-Chloroasimilobine MQ02-439 (S)-Glaucine References Category:5-HT2A agonists Category:5-HT2C agonists Category:Hydroxyarenes Category:Methallyl compounds Category:Noraporphines