11-Chloroasimilobine

11-Chloroasimilobine, also known as 1-methoxy-2-hydroxy-11-chloronoraporphine, is a serotonin 5-HT_2C 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]

Other names11-Chloroasimilobine; 1-Methoxy-2-hydroxy-11-chloronoraporphine; Compound 16k; Compound S11; 1-Methoxy-2-hydroxy-11-chloro-aporphine

Drug classSerotonin 5-HT_2C receptor agonist

ATC code

• None

PubChem CID

• 175794272

Quick facts Clinical data, Other names ...

11-Chloroasimilobine

Clinical data
Other names	11-Chloroasimilobine; 1-Methoxy-2-hydroxy-11-chloronoraporphine; Compound 16k; Compound S11; 1-Methoxy-2-hydroxy-11-chloro-aporphine
Drug class	Serotonin 5-HT2C receptor agonist
ATC code	None
Identifiers
IUPAC name 11-chloro-1-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol
PubChem CID	175794272
Chemical and physical data
Formula	C17H16ClNO2
Molar mass	301.77 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=C(C=C2CCNC3C2=C1C4=C(C3)C=CC=C4Cl)O
InChI 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

Close

The drug acts as a highly selective G_q-preferring biased agonist of the serotonin 5-HT_2C receptor.^[1][2] Its EC₅₀Tooltip half-maximal effective concentration (E_maxTooltip maximal efficacy) values were 36 nM (102%) for G_q signaling and 437 nM (62%) for β-arrestin2 recruitment.^[1] 11-Chloroasimilobine was inactive as an agonist of the serotonin 5-HT_2A and 5-HT_2B receptors at concentrations of up to 30,000 nM.^[1] It was also selective for the serotonin 5-HT_2C 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]