Prenderol

Prenderol
Identifiers
  • 2,2-diethyl-1,3-propanediol
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.003.731 Edit this at Wikidata
Chemical and physical data
FormulaC7H16O2
Molar mass132.203 g·mol−1
3D model (JSmol)
Melting point59–62 °C (138–144 °F)
  • CCC(CC)(CO)CO
  • InChI=1S/C7H16O2/c1-3-7(4-2,5-8)6-9/h8-9H,3-6H2,1-2H3
  • Key:XRVCFZPJAHWYTB-UHFFFAOYSA-N

Prenderol (Diethylpropanediol) is a simple alkyl diol which has sedative, anticonvulsant and muscle relaxant effects. It is closely related in structure to meprobamate and numerous other alkyl alcohols and diols with generally comparable activity.

Synthesis

Treatment of the aldehyde 2-ethylbutyraldehyde with formaldehyde and potassium hydroxide gives a crossed Cannizzaro reaction yielding prenderol.

See also

References

  1. ↑ Berger FM (June 1949). "Anticonvulsant action of 2-substituted-1,3-propanediols". Proceedings of the Society for Experimental Biology and Medicine. 71 (2). New York, N.Y.: 270–271. doi:10.3181/00379727-71-17159. PMID 18134033. S2CID 32255832.
  2. ↑ Funderburk WH, Unna KR (March 1953). "Site of action of 2, 2-diethyl-1,3-propanediol (prenderol) on the central nervous system". The Journal of Pharmacology and Experimental Therapeutics. 107 (3): 344–55. PMID 13035673.
  3. ↑ Mailer AB (July 1954). "Effects of mephenesin and prenderol on intellectual functions of mental patients". Journal of Clinical Psychology. 10 (3): 283–5. doi:10.1002/1097-4679(195407)10:3<283::aid-jclp2270100322>3.0.co;2-a. PMID 13163224.
  4. ↑ Blum B (May 1962). "Head shaking and nystagmus produced by 2,2-diethyl, 1,3-propanediol (prenderol) in the rat". Archives Internationales de Pharmacodynamie et de Therapie. 137: 128–36. PMID 13870189.
  5. ↑ Reyes Q., Aaurelio; Mascetti V., G.; Martinez J., Rolando. Synthesis of polyhydroxylated alcohols. Revista Latinoamericana de Quimica 1984; 15 (1): 29-30. ISSN: 0370-5943.
  6. ↑ Wang G, Lu Q (October 2013). "A nitrate ester of sedative alkyl alcohol improves muscle function and structure in a murine model of Duchenne muscular dystrophy". Molecular Pharmaceutics. 10 (10): 3862–70. doi:10.1021/mp400310r. PMID 23924275.
  7. ↑ McKusick, B. (1948). "New Compounds. New Compounds as Insect Repellents". Journal of the American Chemical Society. 70 (5): 1982–1983. doi:10.1021/ja01185a602.