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11-Chloroasimilobine

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11-Chloroasimilobine
BERJAYA
Clinical data
Other names11-Chloroasimilobine; 1-Methoxy-2-hydroxy-11-chloronoraporphine; Compound 16k; Compound S11; 1-Methoxy-2-hydroxy-11-chloro-aporphine
Drug classSerotonin 5-HT2C receptor agonist
ATC code
  • None
Identifiers
  • 11-chloro-1-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol
PubChem CID
Chemical and physical data
FormulaC17H16ClNO2
Molar mass301.77 g·mol−1
3D model (JSmol)
  • COC1=C(C=C2CCNC3C2=C1C4=C(C3)C=CC=C4Cl)O
  • InChI=1S/C17H16ClNO2/c1-21-17-13(20)8-10-5-6-19-12-7-9-3-2-4-11(18)14(9)16(17)15(10)12/h2-4,8,12,19-20H,5-7H2,1H3
  • Key:IPWPEVUQAYSYTJ-UHFFFAOYSA-N

11-Chloroasimilobine, also known as 1-methoxy-2-hydroxy-11-chloronoraporphine, is a serotonin 5-HT2C receptor agonist of the noraporphine family.[1][2] It is a synthetic compound and is the racemic 11-chloro derivative of the aporphine alkaloid asimilobine.[1][2]

The drug acts as a highly selective Gq-preferring biased agonist of the serotonin 5-HT2C receptor.[1][2] Its EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy) values were 36 nM (102%) for Gq signaling and 437 nM (62%) for β-arrestin2 recruitment.[1] 11-Chloroasimilobine was inactive as an agonist of the serotonin 5-HT2A and 5-HT2B receptors at concentrations of up to 30,000 nM.[1] It was also selective for the serotonin 5-HT2C receptor over a panel of other targets.[1] The drug has been found to reverse the hyperlocomotion induced by dizocilpine (MK801) and phencyclidine (PCP) in rodents.[1] The pharmacokinetics of 11-chloroasimilobine have been studied.[1]

The chemical synthesis of the compound has been described.[1][2]

11-Chloroasimilobine was 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.
  2. 1 2 3 4 5 "Aporphine derivative and preparation method and application thereof". Google Patents. 14 June 2022. Retrieved 4 April 2026.
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