Ortho-Methoxyphenylpiperazine Explained

Drug Name:ortho-Methoxyphenylpiperazine
Class:Serotonin 5-HT1A receptor agonist; Antipsychotic; Antihypertensive
Cas Number:35386-24-4
Pubchem:1346
Unii:81NJO1330A
Chebi:104020
Chembl:9666
Synonyms:o-Methoxyphenylpiperazine; oMeOPP; 2-Methoxyphenylpiperazine; 2-MeOPP
Iupac Name:1-(2-methoxyphenyl)piperazine
C:11
H:16
N:2
O:1
Smiles:COC1=CC=CC=C1N2CCNCC2
Stdinchi:1S/C11H16N2O/c1-14-11-5-3-2-4-10(11)13-8-6-12-7-9-13/h2-5,12H,6-9H2,1H3
Stdinchikey:VNZLQLYBRIOLFZ-UHFFFAOYSA-N

ortho-Methoxyphenylpiperazine (oMeOPP), also known as 2-methoxyphenylpiperazine (2-MeOPP), is a phenylpiperazine derivative which is known to act as a serotonergic agent. Along with various other phenylpiperazines, like benzylpiperazine (BZP) and trifluoromethylphenylpiperazine (TFMPP), oMeOPP has been found in illicit drug samples.[1]

Pharmacology

The drug has been found to have high affinity for the serotonin 5-HT1A receptor, where it acts as a partial agonist (≈ 70%), but shows no affinity for the serotonin 5-HT2 receptor or the dopamine receptors.[2] [3] [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]

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. 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.[6]

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.[7] [8]

Other drugs

oMeOPP has been said to be a metabolite of a variety of drugs including dropropizine, enciprazine, milipertine, MJ-7378, oxypertine, and urapidil.[9] [10] [11] Certain other drugs, such as solypertine, also contain oMeOPP within their chemical structures.[12] However, subsequent research found that oMeOPP is not a metabolite of enciprazine.[13]

See also

Notes and References

  1. Book: White P . Crime Scene to Court: The Essentials of Forensic Science . Royal Society of Chemistry . 2010 . 978-1-84755-882-4 . 30 October 2024 . 370.
  2. Glennon RA . Concepts for the design of 5-HT1A serotonin agonists and antagonists . Drug Development Research . Wiley . 26 . 3 . 1992 . 0272-4391 . 10.1002/ddr.430260306 . 251–274.
  3. Martin GE, Elgin RJ, Kesslick JM, Baldy WJ, Mathiasen JR, Shank RP, Scott MK . Block of conditioned avoidance responding in the rat by substituted phenylpiperazines . European Journal of Pharmacology . 156 . 2 . 223–229 . November 1988 . 3240768 . 10.1016/0014-2999(88)90325-1 .
  4. Lyon RA, Titeler M, McKenney JD, Magee PS, Glennon RA . Synthesis and evaluation of phenyl- and benzoylpiperazines as potential serotonergic agents . Journal of Medicinal Chemistry . 29 . 5 . 630–634 . May 1986 . 3701781 . 10.1021/jm00155a008 .
  5. Gatch MB . Discriminative stimulus effects of m-chlorophenylpiperazine as a model of the role of serotonin receptors in anxiety . Life Sciences . 73 . 11 . 1347–1367 . August 2003 . 12850497 . 10.1016/s0024-3205(03)00422-3 .
  6. Evenden JL . Effects of 8-hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT) after repeated administration on a conditioned avoidance response (CAR) in the rat . Psychopharmacology . 109 . 1–2 . 134–144 . 1992 . 1365647 . 10.1007/BF02245491 . Martin et al. (1988) tested the rather less selective, substituted phenyl piperazine 5-HT agonists, OMPP (ortho-methoxyphenylpiperazine) and MCPP (meta-chlorophenylpiperazine) in a lever-press CAR test, and came to the conclusion that the impairment in CAR induced by OMPP was mediated by the compound's interaction at the 5-HT1A binding site. In passing, it may be noted that the 5-HT1A agonist, buspirone, also impairs CAR, although this effect may be due to the dopamine D2 antagonist effects of this drug (Allen et al. 1974). .
  7. Book: Schlittler E, Druey J, Marxer A . Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques . Antihypertensive Agents . Fortschritte der Arzneimittelforschung. Progress in Drug Research. Progres des Recherches Pharmaceutiques . Birkhäuser Basel . Basel . 1962 . 4 . 978-3-0348-7046-7 . 10.1007/978-3-0348-7044-3_3 . 295–351. 13991862 .
  8. Page IH, Wolford RW, Corcoran AC . Pharmacological and clinical observations on 1-(2-methoxypheny1 piperazine) . Archives Internationales de Pharmacodynamie et de Therapie . 119 . 1–2 . 214–224 . March 1959 . 13628280 .
  9. Elliott S . Current awareness of piperazines: pharmacology and toxicology . Drug Testing and Analysis . 3 . 7–8 . 430–438 . 2011 . 21744514 . 10.1002/dta.307 . Furthermore, oMeOPP is a metabolite of some prescribed drugs: enciprazione, milipertine, urapidil, dropropizine and oxypertine.[1,47] .
  10. Caccia S, Notarnicola A, Fong MH, Benfenati E . Identification and quantitation of 1-arylpiperazines, metabolites resulting from side-chain cleavage of (4-substituted aryl-1-piperazinyl)alkyl heterocyclic derivatives in rat plasma and brain . Journal of Chromatography . 283 . 211–221 . January 1984 . 6707118 . 10.1016/s0021-9673(00)96256-3 .
  11. Benfenati E, Caccia S, Della Vedova F . 1-(o-Methoxyphenyl)piperazine is a metabolite of drugs bearing a methoxyphenylpiperazine side-chain . The Journal of Pharmacy and Pharmacology . 39 . 4 . 312–313 . April 1987 . 2884299 . 10.1111/j.2042-7158.1987.tb06275.x .
  12. Web site: Solypertine . PubChem . 30 October 2024.
  13. Scatina JA, Lockhead SR, Cayen MN, Sisenwine SF . Metabolic disposition of enciprazine, a non-benzodiazepine anxiolytic drug, in rat, dog and man . Xenobiotica; the Fate of Foreign Compounds in Biological Systems . 21 . 12 . 1591–1604 . December 1991 . 1686125 . 10.3109/00498259109044408 .

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