Batoprazine

Batoprazine is a drug of the phenylpiperazine class which has been described as a serenic or antiaggressive agent.[1][2] It acts as a 5-HT1A and 5-HT1B receptor agonist.[2][3] It is closely related to eltoprazine, fluprazine, and naphthylpiperazine, of which possess similar actions and effects.[3]

Batoprazine
Clinical data
Other names8-(1-piperazinyl)coumarin;
8-(1-piperazinyl)-2H-
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
IUPAC name
  • 8-(piperazin-1-yl)-2H-chromen-2-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H14N2O2
Molar mass230.267 g·mol−1
3D model (JSmol)
SMILES
  • O=C/2Oc1c(cccc1\C=C\2)N3CCNCC3
InChI
  • InChI=1S/C13H14N2O2/c16-12-5-4-10-2-1-3-11(13(10)17-12)15-8-6-14-7-9-15/h1-5,14H,6-9H2 Y
  • Key:MTYYDFXUUJQQRS-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Synthesis
Patent:[4] 8-Aminocoumarin:[5] 8-Nitrocoumarin:[6][7]
  • 8-Nitrocoumarin can be obtained in various methods, for example through nitration of coumarin.
  • 8-Aminocoumarin was obtained from reduction of the corresponding nitrated derivative.
  • Ex 7 to 10: The 8-aminocoumarin [75487-97-7] (1) is reacted with an excess of bis(2-chloroethyl)amine hydrochloride [821-48-7] (2) in the presence of potassium carbonate and then of potassium iodide, the reaction being carried out under reflux in chlorobenzene.

See also
  • Phenylpiperazine

References
  1. Olivier B (December 2004). "Serotonin and aggression". Annals of the New York Academy of Sciences. 1036: 382–92. doi:10.1196/annals.1330.022. PMID 15817750. S2CID 45595253.
  2. Olivier B, van Oorschot R (December 2005). "5-HT1B receptors and aggression: a review". European Journal of Pharmacology. 526 (1–3): 207–17. doi:10.1016/j.ejphar.2005.09.066. PMID 16310769.
  3. Gommans J, Hijzen TH, Maes RA, Olivier B (1997). "Discriminative stimulus properties of eltoprazine". Life Sciences. 61 (1): 11–9. doi:10.1016/S0024-3205(97)00352-4. PMID 9200664.
  4. Jean-Louis Peglion, Mark Millan, Jean-Michel Rivet, U.S. Patent 5,194,437 (1993 to Adir Et Compagnie).
  5. Reppel, L.; Schmollack, W. (1963). "Beiträge zur Kenntnis der Cumarine. 2. Mitt.: Die Darstellung von Aminocumarinen". Archiv der Pharmazie. 296 (6): 365–369. doi:10.1002/ardp.19632960603.
  6. Shockravi, A., Valizadeh, H., Heravi, M. M. (1 March 2003). "A One-Pot and Convenient Synthesis of Coumarins in Solventless System". Phosphorus, Sulfur, and Silicon and the Related Elements. 178 (3): 501–504. doi:10.1080/10426500307915.
  7. Ramana, M. M. V., Malik, S. S., Parihar, J. A. (November 2004). "Guanidinium nitrate: a novel reagent for aryl nitrations". Tetrahedron Letters. 45 (47): 8681–8683. doi:10.1016/j.tetlet.2004.09.140.
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