Benocyclidine: Everything you need to know

Overview

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• Source: Microbioz India, Editorial


• Date: 05 Mar,2023

Benocyclidine is a recreationally used psychoactive substance that is related to phencyclidine. Benocyclidine is a member of the arylcyclohexylamine class of drugs. It is also known by the acronym BTCP, which stands for benzothiophenylcyclohexylpiperidine (PCP). In 1997, a patent application authored by Marc Caron and colleagues at Duke University included the first description of the invention. In addition to its role as a psychostimulant, it is also a powerful and selective dopamine reuptake inhibitor (DRI).

Benocyclidine is a pure DRI that has almost no affinity for the NMDA receptor. As a result, it does not possess any anticonvulsant, anaesthetic, hallucinogenic, or dissociative properties. It was utilised in the labelling process for the dopamine transporter. BCP was utilised in an effort to identify a pharmacophore that is shared by DRI-type stimulants.

Benocyclidine Chemical Structure: Image Credit_wikkipedia

Dopamine is involved in a number of critical processes throughout the body and the brain. Dopamine is a neurotransmitter that plays an important role in behaviour that is motivated by rewards, as well as in the regulation of motor function and the release of a number of different hormones. Dopamine system dysfunctions have been linked to a number of important diseases, including schizophrenia, addiction, Attention Deficit Hyperactivity disorder (ADHD), and Parkinson’s disease. Dopamine also plays a role in the digestive system, the immune system, the kidneys, and the pancreas, in addition to the blood vessels.

Benocyclidine, also known as BTCP, was derived from phencyclidine (PCP), but it contained a benzothiophenyl group rather than a phenyl ring in its chemical structure. The inhibition of dopamine (DA) uptake by BTCP was quite potent, with an IC50 value of 7-8 nM. With an IC50 value of 6 μM, BTCP demonstrated a low affinity for the PCP receptor. Both unlabelled BTCP and nomifensine were able to inhibit BTCP binding in the striatum in a dose-dependent manner, with the ID50 values for each compound being 6.34 and 11.06 mg/kg, respectively. In vivo studies on mice showed that BTCP was able to bind to the dopamine uptake complex.

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References:

1. [Vignon J, Pinet V, Cerruti C, et al.  [3H] N-[1-(2-Benzo (b) thiophenyl) cycohexyl] piperidine ([3H] BTCP): a new phencyclidine analog selective for the dopamine uptake complex[J]. European journal of pharmacology, 1988, 148(3): 427-436.
2. Chaudieu I, Vignon J, Chicheportiche M, et al.  Role of the aromatic group in the inhibition of phencyclidine binding and dopamine uptake by PCP analogs[J]. Pharmacology Biochemistry and Behavior, 1989, 32(3): 699-705.
3. Seeman P.  Brain dopamine receptors[J]. Pharmacological Reviews, 1980, 32(3): 229-313.
4. Maurice T, Vignon J, Kamenka J M, et al.  In vivo labelling of the mouse dopamine uptake complex with the phencyclidine derivative [3 H] BTCP[J]. Neuroscience letters, 1989, 101(2): 234-238.