Enadoline
Encyclopedia
Enadoline is a drug which acts as a highly selective κ-opioid
Kappa Opioid receptor
The κ-opioid receptor is a protein that in humans is encoded by the OPRK1 gene. The κ-opioid receptor is one of five related receptors that bind opium-like compounds in the brain and are responsible for mediating the effects of these compounds...

 agonist
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...

.

In human studies, it produced visual distortions and feelings of dissociation
Dissociation
Dissociation is an altered state of consciousness characterized by partial or complete disruption of the normal integration of a person’s normal conscious or psychological functioning. Dissociation is most commonly experienced as a subjective perception of one's consciousness being detached from...

, reminiscent of the effects of Salvinorin A
Salvinorin A
Salvinorin A is the main active psychotropic molecule in Salvia divinorum, a Mexican plant which has a long history of use as an entheogen by indigenous Mazatec shamans...

.

It was looked at as a potential analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....

, but abandoned because of the dose-limiting effects of dysphoria
Dysphoria
Dysphoria is medically recognized as a mental and emotional condition in which a person experiences intense feelings of depression, discontent and indifference to the world around them.Mood disorders can induce dysphoria, often with a heightened risk of suicide, especially in...

, which could be expected from a κ-opioid agonist. There was mention of its potential in treating coma
Coma
In medicine, a coma is a state of unconsciousness, lasting more than 6 hours in which a person cannot be awakened, fails to respond normally to painful stimuli, light or sound, lacks a normal sleep-wake cycle and does not initiate voluntary actions. A person in a state of coma is described as...

tose head injury or stroke
Stroke
A stroke, previously known medically as a cerebrovascular accident , is the rapidly developing loss of brain function due to disturbance in the blood supply to the brain. This can be due to ischemia caused by blockage , or a hemorrhage...

 victims, where that type of side effect would be immaterial.

Synthesis

The chemical synthesis of enadoline is similar to that of the related compound spiradoline
Spiradoline
Spiradoline is a drug which acts as a highly selective κ-opioid agonist. It has analgesic, diuretic and antitussive effects, and produces subjective effects in animals similar to those of ketocyclazocine and allylnormetazocine...

, since both compounds share the same intermediate and only differ from one another with respect to the final step.
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