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Pipofezine

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Pipofezine
Clinical data
Trade namesAzafen, Azaphen
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 5-methyl-3-(4-methylpiperazin-1-yl)pyridazino[3,4-b][1,4]benzoxazine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H19N5O
Molar mass297.362 g·mol−1

Pipofezine, sold under the brand name Azafen or Azaphen, is an antidepressant approved in Russia for the treatment of depression.[1][2][3][4] It was introduced in the late 1960s and is still used today.[5][6]

Pipofezine has been shown to act as a potent inhibitor of the reuptake of serotonin.[7][8] In addition to its antidepressant action, pipofezine has sedative effects as well, suggesting antihistamine activity.[4] Other properties such as anticholinergic or antiadrenergic actions are less clear but are likely.[citation needed]

Synthesis

Patent:[9] Precursor:[10][11]

2-Benzoxazolinone [59-49-4] (1) is treated with dimethylsulfate in aqueous KOH solution to give 3-Methyl-2-Benzoxazolinone [21892-80-8] (2). This is further reacted with 3,4,6-Trichloropyridazine [6082-66-2] (3) catalyzed by KOH in ethanol solvent to give 2-Chloro-10-methyl-3,4-diazaphenoxazine [27225-84-9] (4)

Ex 7: Alkylation with Methylpiperazine (5) in cyclohexanol, with azeotropic removal of the solvent gives pipofezine (3).

References

  1. ^ Aleeva GN, Molodavkin GM, Voronina TA (July 2009). "Comparison of antidepressant effects of azafan, tianeptine, and paroxetine". Bulletin of Experimental Biology and Medicine. 148 (1): 54–6. doi:10.1007/s10517-009-0638-4. PMID 19902096. S2CID 23923093.
  2. ^ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.
  3. ^ European Drug Index, 4th Edition. Boca Raton: CRC Press. 1998. ISBN 3-7692-2114-1.
  4. ^ a b John E. Macor (2009). Annual Reports in Medicinal Chemistry, Volume V44. Boston: Academic Press. ISBN 978-0-12-374766-2.
  5. ^ Mashkovskii MD; Polezhaeva AI; Avrutskii GIa; Vertozgadova OP; Smulevich AB (1969). "[The pharmacologic properties and therapeutic effectiveness of the new antidepressant preparation Azaphen]". Zhurnal Nevropatologii i Psikhiatrii Imeni S.S. Korsakova (in Russian). 69 (8): 1234–8. PMID 5392529.
  6. ^ Shinaev NN, Akzhigitov RG (2005). "[Azaphen: a return to clinical practice]". Zhurnal Nevrologii i Psikhiatrii Imeni S.S. Korsakova (in Russian). 105 (10): 55–6. PMID 16281382.
  7. ^ Avdulov NA, Maĭsov NI (November 1981). "[Atypical antidepressants: effect on synaptosomal uptake of serotonin and GABA]". Biulleten' Eksperimental'noĭ Biologii i Meditsiny (in Russian). 92 (11): 564–6. PMID 7198493.
  8. ^ Valdman AV, Avdulov NA, Rozganets VV, Rusacov DY (1983). "Behavioural and neurochemical studies of the action of atypical antidepressants". Acta Physiologica et Pharmacologica Bulgarica. 9 (3): 3–10. PMID 6142583.
  9. ^ Anon, FR 1576534  (1969-08-01).
  10. ^ Gortinskaya, T. V., Nyrkova, V. G., Savitskaya, N. V., Shchukina, M. N. (June 1971). "Synthesis of substituted 5H-pyradazino [3,4-b]-1,4-benzoxazine (3,4-diazaphenoxazine): III. Synthesis of 2-chloro-10-alkyl- and 2-chloro-10-dialkylaminoalkyl-3,4-diazaphenoxazines". Chemistry of Heterocyclic Compounds. 7 (6): 698–702. doi:10.1007/BF00476810. eISSN 1573-8353. ISSN 0009-3122.
  11. ^ Tatyana Vladimirovna Gortinskaya, et al. U.S. patent 3,961,058 (1976 to Moscow, USSR).


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