Oxypertine

Last updated

Oxypertine
Oxypertine.svg
Clinical data
Trade names Oxypertine, others
Other namesWIN-18501; WIN18501; WIN-18,501, Win-18501; Win-18501-2
AHFS/Drugs.com International Drug Names
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances) [1]
  • In general: ℞ (Prescription only)
Identifiers
  • 5,6-Dimethoxy-2-methyl-3-[2-(4-phenylpiperazin-1-yl)ethyl]-1H-indole
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.005.291 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C23H29N3O2
Molar mass 379.504 g·mol−1
3D model (JSmol)
  • CC1=C(C2=CC(=C(C=C2N1)OC)OC)CCN3CCN(CC3)C4=CC=CC=C4
  • InChI=1S/C23H29N3O2/c1-17-19(20-15-22(27-2)23(28-3)16-21(20)24-17)9-10-25-11-13-26(14-12-25)18-7-5-4-6-8-18/h4-8,15-16,24H,9-14H2,1-3H3 X mark.svgN
  • Key:XCWPUUGSGHNIDZ-UHFFFAOYSA-N X mark.svgN
   (verify)

Oxypertine, sold under the brand name Oxypertine among others, is an antipsychotic medication of the tryptamine and phenylpiperazine groups which was previously used in the treatment of schizophrenia but is no longer marketed. [2] It was also evaluated for the treatment of anxiety. [3]

Contents

Pharmacology

Pharmacodynamics

The drug shows high affinity for the serotonin 5-HT2 and dopamine D2 receptors (Ki = 8.6 nM and 30 nM, respectively). [4] It antagonizes the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals. [4] [5] Like reserpine and tetrabenazine, oxypertine depletes catecholamines, though not serotonin, possibly contributing to its antipsychotic effectiveness. [6]

Chemistry

Chemically, it is a substituted tryptamine and phenylpiperazine derivative. [7] Its chemical structure is similar to other "pertines" including alpertine, milipertine, and solypertine. [8] [9]

History

Oxypertine was first described in the scientific literature by 1962. [10]

Society and culture

Names

Oxypertine is the generic name of the drug and its INN Tooltip International Nonproprietary Name, USAN Tooltip United States Adopted Name, BAN Tooltip British Approved Name, DCF Tooltip Dénomination Commune Française, and JAN Tooltip Japanese Accepted Name. [10] [11] [12] [13] It is also known by its former developmental code name WIN-18501. [10] [11] [12] [13] The drug has been sold under brand names including Equipertine, Forit, Integrin, Lanturil, Lotawin, Opertil, and Oxypertine. [10] [11] [12] [13]

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Tepirindole (INNTooltip International Nonproprietary Name; developmental code names RU-27592, HR-592) is a tryptamine-related atypical antipsychotic and major tranquilizer which was never marketed. It is similar in structure to tryptamines but is not technically a tryptamine itself and is instead a piperidinyl indole. The drug is said to act on dopamine D2, serotonin 5-HT2, and α1-adrenergic receptors. It is a potent dopamine receptor antagonist but reportedly has little propensity to cause catalepsy and has been said to potentially be useful in treating the negative symptoms of schizophrenia. The drug may also act as a potent serotonin receptor agonist. Tepirindole was first described in the literature by 1979.

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<span class="mw-page-title-main">Solypertine</span> Abandoned sympatholytic drug

Solypertine, also known as solypertine tartrate in the case of the tartrate salt, is a drug described as an antiadrenergic and as also potentially possessing neuroleptic properties which was never marketed.

<i>ortho</i>-Methoxyphenylpiperazine Serotonergic drug

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.

References

  1. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ↑ Hall C, Rhodes PH (1996). Dictionary of organic compounds. London: Chapman & Hall. ISBN   0-412-54090-8.
  3. ↑ Somohano MD, Broissin MC, Sobrino ZA (1976). "[Clinical evaluation of oxypertine in anxiety conditions]". Neurologia, Neurocirugia, Psiquiatria (in Spanish). 17 (3): 171–180. PMID   12484.
  4. 1 2 Megens AA, Kennis LE (1996). "Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent?". Progress in Medicinal Chemistry. 33: 185–232. doi:10.1016/s0079-6468(08)70306-0. ISBN   978-0-444-82310-6. PMID   8776944.{{cite journal}}: Cite journal requires |journal= (help)
  5. ↑ Niemegeers CJ, Janssen PA (June 1979). "A systematic study of the pharmacological activities of dopamine antagonists". Life Sciences. 24 (24). Elsevier BV: 2201–2216. doi:10.1016/0024-3205(79)90096-1. PMID   388130.
  6. ↑ Bak IJ, Hassler R, Kim JS (1969). "Differential monoamine depletion by oxypertine in nerve terminals. Granulated synaptic vesicles in relation to depletion of norepinephrine, dopamine and serotonin". Zeitschrift Fur Zellforschung und Mikroskopische Anatomie. 101 (3): 448–462. doi:10.1007/BF00335580. PMID   5362847. S2CID   32583722.
  7. ↑ Breulet M, Labar P, Delree C, Collard J, Bobon J (February 1968). "[Oxypertine, peperazine derivative of tryptophan with neuroleptic and dynamogenic properties]". Acta Neurologica et Psychiatrica Belgica (in French). 68 (2): 116–127. PMID   4972600.
  8. ↑ Ellis GP, Luscombe DK (1996). Progress in Medicinal Chemistry. Elsevier Science. p. 219. ISBN   978-0-08-086281-1 . Retrieved 30 October 2024. Pertines (class 7; Table 5.12) The pertines oxypertine, solypertine, milipertine, and alpertine are piperazinylethylindoles.
  9. ↑ Lednicer D, Mitscher LA (1980). The Organic Chemistry of Drug Synthesis, Volume 2. Organic Chemistry Series of Drug Synthesis. Wiley. pp. 341–343. ISBN   978-0-471-04392-8 . Retrieved 30 October 2024.
  10. 1 2 3 4 Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 924. ISBN   978-1-4757-2085-3 . Retrieved 2 November 2024.
  11. 1 2 3 Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 779. ISBN   978-3-88763-075-1 . Retrieved 2 November 2024.
  12. 1 2 3 Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 212. ISBN   978-94-011-4439-1 . Retrieved 2 November 2024.
  13. 1 2 3 "List of Antipsychotics". Archived from the original on 2016-03-03.


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