Ortho-Methoxyphenylpiperazine
Serotonergic drug
From Wikipedia, the free encyclopedia
ortho-Methoxyphenylpiperazine (oMeOPP), also known as 2-methoxyphenylpiperazine (2-MeOPP), is a phenylpiperazine derivative which is known to act as a serotonergic agent.[1][2] Along with various other phenylpiperazines, like benzylpiperazine (BZP) and trifluoromethylphenylpiperazine (TFMPP), oMeOPP has been found in illicit drug samples.[3]
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| Other names | o-Methoxyphenylpiperazine; oMeOPP; 2-Methoxyphenylpiperazine; 2-MeOPP |
| Drug class | Serotonin 5-HT1A receptor agonist; Antipsychotic; Antihypertensive[1][2] |
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| ECHA InfoCard | 100.047.747 |
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| Formula | C11H16N2O |
| Molar mass | 192.262 g·mol−1 |
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Pharmacology
The drug has been found to have high affinity for the serotonin 5-HT1A receptor, where it acts as a partial agonist (Emax ≈ 70%), but shows no affinity for the serotonin 5-HT2 receptor or the dopamine receptors.[1][2][4] This is in contrast to the related drug meta-chlorophenylpiperazine (mCPP), which shows high affinity for both the serotonin 5-HT1A and 5-HT2 receptors.[5][2]
oMeOPP and mCPP have both been found to suppress conditioned avoidance responses (CARs) without markedly affecting escape behavior in animals, indicative that they have antipsychotic-like effects.[2] The serotonin receptor antagonist metergoline reversed the suppression of CARs by mCPP but not by oMeOPP.[2] oMeOPP also reversed amphetamine-induced stereotypy in animals, whereas mCPP did not do so.[2] The suppression of CARs by oMeOPP may be mediated by serotonin 5-HT1A receptor activation.[6][2]
In contrast to other related phenylpiperazines, which are known to act as monoamine releasing agents and/or reuptake inhibitors, the activities of oMeOPP at the monoamine transporters do not appear to have been described.[7][8][9][10][11]
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.[2][12][13]
Other drugs
oMeOPP has been said to be a metabolite of a variety of drugs including dropropizine, enciprazine, milipertine, MJ-7378, oxypertine, and urapidil.[14][15][16][17] Certain other drugs, such as solypertine, also contain oMeOPP within their chemical structures.[18] However, subsequent research found that oMeOPP is not a metabolite of enciprazine.[16]