Xibenolol

Last updated
Xibenolol
Xibenolol.png
Clinical data
ATC code
  • none
Identifiers
  • 1-(tert-Butylamino)-3-(2,3-dimethylphenoxy)propan-2-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C15H25NO2
Molar mass 251.370 g·mol−1
3D model (JSmol)
  • O(c1cccc(c1C)C)CC(O)CNC(C)(C)C

Xibenolol is a beta blocker. [1] [2]

Synthesis

Thieme ChemDrug Synthesis: Patents: Xibenolol synthesis.svg
Thieme ChemDrug Synthesis: Patents:

2,3-Xylenol [526-75-0] (1) And 1-Tert-Butyl-3-Azetidinol [13156-04-2] (2).

In the conventional way though, epichlorohydrin and tert-butylamine sequentially.

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References

  1. "The Use of Common Stems in the Selection of International Nonproprietary Names (INN) for Pharmaceutical Substances: Alphabetical list of stems together with corresponding INNs". Archived from the original on March 7, 2012.
  2. Honma S, Ito T, Kambegawa A (February 1985). "Stereoselectivity in the metabolism of the beta-adrenergic blocking agent, (+/-)-1-tert-butylamino-3-(2,3-dimethylphenoxy)-2-propanol hydrochloride (xibenolol hydrochloride, D-32), in man". Chemical & Pharmaceutical Bulletin. 33 (2): 760–8. doi: 10.1248/cpb.33.760 . PMID   2861914.
  3. Castaer, J.; Weetman, DF; D-32. Drugs Fut 1977, 2, 2, 91.
  4. DE1236523 idem Koch Conrad, Raymond J Geus, Jacobi Haireddin, Kunz Wilhelm, U.S. Patent 3,309,406 (1967 to Sanol Arznei Schwarz Gmbh).
  5. Kunio Tsukamoto, Yasushi Suzuki, Akihiro Izumi, Yoshio Hiramatsu, U.S. Patent 4,018,824 (1977 to Teikoku Hormone Mfg. Co., Ltd.).