11-Chloroasimilobine

vanc 6 11-Chloroasimilobine.svg skin-invert-image 200px Serotonin 5-HT2C receptor agonist None 175794272 11-Chloroasimilobine; 1-Methoxy-2-hydroxy-11-chloronoraporphine; Compound 16k; Compound S11; 1-Methoxy-2-hydroxy-11-chloro-aporphine 11-chloro-1-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol 17 16 1 1 2 COC1=C(C=C2CCNC3C2=C1C4=C(C3)C=CC=C4Cl)O 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 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. Qin W, Zhang B, Wang Q, Jiang G, Cui J, Chen F, Wang L, Chen J, Tian S, Zhen XC, Shui W, Ye N 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 November 2025 41108743 10.1021/acs.jmedchem.5c02115 Aporphine derivative and preparation method and application thereof Google Patents 14 June 2022 https://patents.google.com/patent/CN115108986A/en 4 April 2026 It is a synthetic compound and is the racemic 11-chloro derivative of the aporphine alkaloid asimilobine. The drug acts as a highly selective Gq-preferring biased agonist of the serotonin 5-HT2C receptor. Its EC50 half-maximal effective concentration (Emax maximal efficacy) values were 36nM (102%) for Gq signaling and 437nM (62%) for β-arrestin2 recruitment. 11-Chloroasimilobine was inactive as an agonist of the serotonin 5-HT2A and 5-HT2B receptors at concentrations of up to 30,000nM. It was also selective for the serotonin 5-HT2C receptor over a panel of other targets. The drug has been found to reverse the hyperlocomotion induced by dizocilpine (MK801) and phencyclidine (PCP) in rodents. The pharmacokinetics of 11-chloroasimilobine have been studied. The chemical synthesis of the compound has been described. 11-Chloroasimilobine was described in the scientific literature by Wangzhi Qin and colleagues in 2025. It had previously been patented in 2022. See also Serotonin 5-HT2C receptor agonist Aporphine alkaloids MQ02-439 Asimilobine Glaucine Nuciferine References Category:5-HT2C agonists Category:Biased ligands Category:Chloroarenes Category:Hydroxyarenes Category:Methoxy compounds Category:Noraporphines