Ortho-Methoxyphenylpiperazine


ortho-Methoxyphenylpiperazine, also known as 2-methoxyphenylpiperazine, is a phenylpiperazine derivative which is known to act as a serotonergic agent. Along with various other phenylpiperazines, like benzylpiperazine and trifluoromethylphenylpiperazine, oMeOPP has been found in illicit drug samples.

Pharmacology

The drug has been found to have high affinity for the serotonin 5-HT1A receptor, where it acts as a partial agonist, but shows no affinity for the serotonin 5-HT2 receptor or the dopamine receptors. This is in contrast to the related drug meta-chlorophenylpiperazine, which shows high affinity for both the serotonin 5-HT1A and 5-HT2 receptors.
oMeOPP and mCPP have both been found to suppress conditioned avoidance responses without markedly affecting escape behavior in animals, indicative that they have antipsychotic-like effects. The serotonin receptor antagonist metergoline reversed the suppression of CARs by mCPP but not by oMeOPP. oMeOPP also reversed amphetamine-induced stereotypy in animals, whereas mCPP did not do so. The suppression of CARs by oMeOPP may be mediated by serotonin 5-HT1A receptor activation.
In contrast to other related phenylpiperazines, which are known to act as monoamine releasing agents and/or monoamine [reuptake inhibitor|reuptake inhibitor]s, the activities of oMeOPP at the monoamine transporters do not appear to have been described.

History

oMeOPP was studied in the 1950s as an antihypertensive agent and produced side effects such as drowsiness that could be interpreted as antipsychotic-like.

Other drugs

oMeOPP has been said to be a metabolite of a variety of drugs including dropropizine, enciprazine, milipertine, MJ-7378, oxypertine, and urapidil. Certain other drugs, such as solypertine, also contain oMeOPP within their chemical structures. However, subsequent research found that oMeOPP is not a metabolite of enciprazine.