Pyridopyrroloquinoxaline
A substituted pyridopyrroloquinoxaline, or more specifically a substituted octahydro-1H-pyridopyrroloquinoxaline, also known as a substituted heterocycle fused γ-carboline, is a further-cyclized and substituted tetracyclic derivative of the tricyclic alkaloid γ-carboline as well as an analogue of the atypical antipsychotic lumateperone. They can additionally be thought of as analogues of cyclized tryptamines like the β-carbolines or harmala alkaloids such as harmaline, but are not technically tryptamines themselves.
Pyridopyrroloquinoxalines are notable for their varying interactions with the serotonin 5-HT2A receptor as well as with other monoamine receptors. Lumateperone and deulumateperone are serotonin 5-HT2A receptor antagonists with antipsychotic properties, IHCH-7113 is a putatively psychedelic serotonin 5-HT2A receptor full agonist with a robust head-twitch response in rodents, and IHCH-7086, IHCH-7079, and ITI-1549 are putatively non-hallucinogenic β-arrestin-biased serotonin 5-HT2A receptor partial agonists with psychoplastogenic and/or antidepressant-like effects in preclinical studies. The broad receptor interactions of some of these compounds have been studied.
Pyridopyrroloquinoxalines with serotonin 5-HT2A receptor agonistic activity such as IHCH-7113 and IHCH-7086 were first described in the scientific literature by Dongmei Cao and colleagues by 2022. As of 2025, ITI-1549 is under development by Intra-Cellular Therapies for the treatment of mood and other psychiatric disorders.
List of pyridopyrroloquinoxalines
| Structure | Name | Chemical name |
| IHCH-7113 | -3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyridopyrroloquinoxaline | |
| IHCH-7079 | -2,3,6b,7,8,9,10,10a-octahydro-8--3-methyl-1H-pyridopyrroloquinoxaline | |
| IHCH-7086 | -2,3,6b,7,8,9,10,10a-octahydro-8--3-methyl-1H-pyridopyrroloquinoxaline | |
| Lumateperone | 1--4--1-butanone | |
| Deulumateperone | 1--4-pyrroloquinoxalin-8-yl]butan-1-one | |
| ITI-1549 | ? |
Other known pyridopyrroloquinoxalines include IHCH-7081, IHCH-7087, IHCH-7088, IHCH-7089, IHCH-7112, and IHCH-7120.
Related compounds
| Structure | Name | Chemical name |
| IHCH-8134 | -8--1,2,6b,7,8,9,10,10a-octahydro-oxazinopyridoindole |