Quipazine is a

serotonergic Serotonergic () or serotoninergic () means "pertaining to or affecting serotonin". Serotonin is a neurotransmitter. A synapse In the nervous system, a synapse is a structure that permits a neuron (or nerve cell) to pass an electrical or chem ...

drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via inhal ...

of the

piperazine Piperazine () is an organic compound that consists of a six-membered ring containing two nitrogen atoms at opposite positions in the ring. Piperazine exists as small alkaline deliquescent crystals with a saline taste. The piperazines are a broad ...

group which is used in

scientific research The scientific method is an empirical method for acquiring knowledge that has characterized the development of science since at least the 17th century (with notable practitioners in previous centuries; see the article history of scientific ...

. It was originally intended as an

antidepressant Antidepressants are a class of medication used to treat major depressive disorder, anxiety disorders, chronic pain conditions, and to help manage addictions. Common side-effects of antidepressants include dry mouth, weight gain, dizziness ...

but never developed for medical use.

Pharmacology

Pharmacodynamics

Quipazine is a

serotonin reuptake inhibitor A serotonin reuptake inhibitor (SRI) is a type of drug which acts as a reuptake inhibitor of the neurotransmitter serotonin (5-hydroxytryptamine, or 5-HT) by blocking the action of the serotonin transporter (SERT). This in turn leads to increa ...

, and also a moderately selective serotonin receptor

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...

, binding to a range of different serotonin receptors, but particularly to the 5-HT_2A and 5-HT₃ subtypes. Quipazine produces a

head-twitch response The head-twitch response (HTR) is a rapid side-to-side head movement that occurs in mice and rats after the serotonin 5-HT2A receptor is activated. The prefrontal cortex may be the neuroanatomical locus mediating the HTR. Many serotonergic halluci ...

and other

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science ...

-consistent effects in animal studies including in mice, rats, and monkeys. However, it failed to produce psychedelic effects in humans at a dose of 25 mg, which was the highest dose tested due to 5-HT₃ mediated side effects of

nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the ...

and gastrointestinal discomfort. However

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamp ...

claimed that a fully effective psychedelic dose could be reached by blocking 5-HT₃ receptors using a 5-HT₃ antagonist.

Chemistry

Quipazine is synthesized by reacting

2-chloroquinoline 2-Chloroquinoline is an organic compound with the formula ClC9H6N. It is one of several isomeric chloro derivatives of the bicyclic heterocycle called quinoline. A white solid, 2-chloroquinoline can be prepared from vinylaniline and phosgene. ...

with

References

{{Piperazines 5-HT3 agonists Abandoned drugs Piperazines Quinolines Serotonin receptor agonists Serotonin reuptake inhibitors

Pharmacology

Pharmacodynamics

Chemistry

See also

References