[go: up one dir, main page]

Jump to content

Hexobendine

From Wikipedia, the free encyclopedia
The printable version is no longer supported and may have rendering errors. Please update your browser bookmarks and please use the default browser print function instead.
Hexobendine
Clinical data
ATC code
Identifiers
  • Ethane-1,2-diylbis[(methylimino)propane-3,1-diyl] bis(3,4,5-trimethoxybenzoate)
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.000.173 Edit this at Wikidata
Chemical and physical data
FormulaC30H44N2O10
Molar mass592.686 g·mol−1
3D model (JSmol)
  • COc1c(cc(cc1OC)C(=O)OCCCN(C)CCN(C)CCCOC(=O)c2cc(OC)c(OC)c(OC)c2)OC
  • InChI=1S/C30H44N2O10/c1-31(11-9-15-41-29(33)21-17-23(35-3)27(39-7)24(18-21)36-4)13-14-32(2)12-10-16-42-30(34)22-19-25(37-5)28(40-8)26(20-22)38-6/h17-20H,9-16H2,1-8H3 ☒N
  • Key:KRQAMFQCSAJCRH-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Hexobendine is a vasodilator that acts as an adenosine reuptake inhibitor.[1]

Synthesis

Hexobendine can be synthesized starting with a reaction between 3,4,5-trimethoxybenzoyl chloride (1) and 3-chloropropanol (2) to give the corresponding ester, 3-chloropropyl 3,4,5-trimethoxybenzoate (3). The last step involves the reaction between two molar equivalents of 3 with one molar equivalent of 1,2-dimethylethylenediamine (4) completing the synthesis of hexobendine (5).[2][3]

Synthesis of hexobendine

See also

References

  1. ^ Kolassa N, Pfleger K (January 1975). "Adenosine uptake by erythrocytes of man, rat and guinea-pig and its inhibition by hexobendine and dipyridamole". Biochemical Pharmacology. 24 (1): 154–6. doi:10.1016/0006-2952(75)90331-7. PMID 1168469.
  2. ^ "Pharmaceutical Substances: Hexobendine". Thieme.
  3. ^ AT231432 idem Schlogl Karl, Kraupp Otto, U.S. patent 3,267,103 (1964 & 1966 to Chemie Linz Ag).