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

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2-Hydroxy-11-(2-methylallyl)oxynoraporphine
Clinical data
Other names"Compound 20s";[1] "Compound S30"[2]
Drug classSerotonin 5-HT2A receptor agonist; Serotonin 5-HT2C receptor agonist
ATC code
  • None
Identifiers
  • 11-(2-methylprop-2-enoxy)-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol
PubChem CID
Chemical and physical data
FormulaC20H21NO2
Molar mass307.393 g·mol−1
3D model (JSmol)
  • CC(=C)COC1=CC=CC2=C1C3=CC(=CC4=C3C(C2)NCC4)O
  • InChI=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
  • Key:QBPVUNKTSFWCKO-UHFFFAOYSA-N

2-Hydroxy-11-(2-methylallyl)oxynoraporphine is a serotonin 5-HT2A and 5-HT2C receptor agonist of the noraporphine family.[1][2] 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.[1][2]

It is a potent full agonist or high-efficacy partial agonist of the serotonin 5-HT2A and 5-HT2C receptors.[1][2] The drug's EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy) values were 6.3 to 9.4 nM (83–84%) at the serotonin 5-HT2A receptor and 8.0 to 9.8 nM (95–103%) at the serotonin 5-HT2C receptor.[1][2] It showed no agonistic activity at the serotonin 5-HT2B receptor at concentrations of up to 30,000 nM.[1][2] 2-Hydroxy-11-(2-methylallyl)oxynoraporphine was among the most potent serotonin 5-HT2A receptor agonists of a large series of assessed noraporphines.[1][2]

The chemical synthesis of 2-hydroxy-11-(2-methylallyl)oxynoraporphine has been described.[1][2] A variety of analogues of the drug with similar activity have also been described.[1][2]

2-Hydroxy-11-(2-methylallyl)oxynoraporphine was first described in the scientific literature by Wangzhi Qin and colleagues in 2025.[1] It had previously been patented in 2022.[2]

See also

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References

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  1. 1 2 3 4 5 6 7 8 9 10 Qin W, Zhang B, Wang Q, Jiang G, Cui J, Chen F, et al. (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. doi:10.1021/acs.jmedchem.5c02115. PMID 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%).
  2. 1 2 3 4 5 6 7 8 9 10 CN 115108986A, Ye N, Shui W, Qin W, Zhang B, Jiang G, "Aporphine derivative and preparation method and application thereof", published 27 September 2022, assigned to Suzhou University and ShanghaiTech University
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