Chemistry:Enciprazine

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Short description: Chemical compound
Enciprazine
Enciprazine.svg
Clinical data
Other namesWY-48624; D-3112
Routes of
administration		Oral
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC23H32N2O6
Molar mass432.517 g·mol−1
3D model (JSmol)

Enciprazine (INN, BAN; enciprazine hydrochloride (USAN); developmental code names WY-48624, D-3112) is an anxiolytic and antipsychotic of the phenylpiperazine class which was never marketed.[1][2][3][4] It shows high affinity for the α1-adrenergic receptor and 5-HT1A receptor, among other sites.[3][5][6] The drug was initially anticipated to produce ortho-methoxyphenylpiperazine (oMeOPP), a serotonin receptor agonist with high affinity for the 5-HT1A receptor, as a significant active metabolite, but subsequent research found this not to be the case.[5]

Synthesis

ChemDrug Synthesis:[7][8][9][10]

3,4,5-trimethoxyphenol (aka Antiarol) [642-71-7] (1) is alkylated with epichlorohydrin (2) to give [(3,4,5-Trimethoxyphenoxy)methyl]oxirane [74760-14-8] (3). Opening of the epoxide with o-anisyl-piperazine [35386-24-4] (4) completes the synthesis of enciprazine (5).

See also

References

  1. ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 485–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA485. 
  2. ↑ Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. pp. 109–. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA109. 
  3. ↑ 3.0 3.1 "Modification of hypothalamic-pituitary-adrenocortical activity by serotonergic agents in the rat". Pharmacology 55 (2): 59–65. 1997. doi:10.1159/000139513. PMID 9323305. 
  4. ↑ "Enciprazine". AdisInsight. Springer Nature Switzerland AG. http://adisinsight.springer.com/drugs/800000720. 
  5. ↑ 5.0 5.1 "Metabolic disposition of enciprazine, a non-benzodiazepine anxiolytic drug, in rat, dog and man". Xenobiotica 21 (12): 1591–604. 1991. doi:10.3109/00498259109044408. PMID 1686125. 
  6. ↑ "Early phase-II semi double-blind study of the new alkaline propanolamine derivative enciprazine (short communication)". Arzneimittelforschung 38 (6): 814–6. 1988. PMID 3178922. 
  7. ↑ "Enciprazine". Drugs of the Future 6 (5): 278. 1981. doi:10.1358/dof.1981.006.05.79478. 
  8. ↑ "Chemistry and pharmacology of the non-benzodiazepine anxiolytic enciprazine and related compounds". Journal of Medicinal Chemistry 33 (11): 2976–81. November 1990. doi:10.1021/jm00173a012. PMID 1977910. 
  9. ↑ "New chemical and chemo-enzymatic routes for the synthesis of (RS)-and (S)-enciprazine.". Tetrahedron: Asymmetry 23 (17): 1272–1278. September 2012. doi:10.1016/j.tetasy.2012.08.002. 
  10. ↑ "A simple and efficient asymmetric synthesis of anxiolytic drug enciprazine.". Synthesis 2010 (16): 2705–2707. August 2010. doi:10.1055/s-0030-1258173. 

External links



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