Gacyclidine
Encyclopedia
Gacyclidine is a psychoactive drug
which acts as a dissociative via functioning as a non-competitive
NMDA receptor
antagonist. It is closely related to phencyclidine
(PCP), and specifically, is a derivative of tenocyclidine
(TCP).
to provide the target compound as a diastereomeric mixture.
Psychoactive drug
A psychoactive drug, psychopharmaceutical, or psychotropic is a chemical substance that crosses the blood–brain barrier and acts primarily upon the central nervous system where it affects brain function, resulting in changes in perception, mood, consciousness, cognition, and behavior...
which acts as a dissociative via functioning as a non-competitive
Non-competitive inhibition
Non-competitive inhibition is a type of enzyme inhibition where the inhibitor reduces the activity of the enzyme, by binding not to the active site on the enzyme, but to a different site...
NMDA receptor
NMDA receptor
The NMDA receptor , a glutamate receptor, is the predominant molecular device for controlling synaptic plasticity and memory function....
antagonist. It is closely related to phencyclidine
Phencyclidine
Phencyclidine , commonly initialized as PCP and known colloquially as angel dust, is a recreational dissociative drug...
(PCP), and specifically, is a derivative of tenocyclidine
Tenocyclidine
Tenocyclidine is a dissociative anesthetic drug with stimulant and hallucinogenic effects. It is similar in effects to phencyclidine but is considerably more potent. TCP has slightly different binding properties to PCP, with more affinity for the NMDA receptors, but less affinity for the sigma...
(TCP).
Synthesis
The condensation of 2-methylcyclohexanone (I) with 2-thienyl lithium (II) or 2-thienylmagnesium bromide (III) gives cyclohexanol (IV) as a diastereomeric mixture, which was treated with Na-N3 in trichloroacetic acid to yield the azide (V). The reduction of (V) with LiAlH4 or RaNi/iPr-OH affords the corresponding amine (VI), preferentially with the cis-configuration. Finally, this compound is condensed with 1,5-dibromopentane (VII) by means of K2CO3 in acetonitrileAcetonitrile
Acetonitrile is the chemical compound with formula . This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture...
to provide the target compound as a diastereomeric mixture.