Prenderol

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Prenderol
Prenderol.svg
Identifiers
  • 2,2-diethyl-1,3-propanediol
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard 100.003.731 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C7H16O2
Molar mass 132.203 g·mol−1
3D model (JSmol)
Melting point 59–62 °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. [1] [2] [3] [4] [5] [6]

Contents

Synthesis

Treatment of the aldehyde 2-ethylbutyraldehyde with formaldehyde and potassium hydroxide gives a crossed Cannizzaro reaction yielding prenderol. [7]

See also

Related Research Articles

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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.