Prenderol

Prenderol
Identifiers
	IUPAC name 2,2-diethyl-1,3-propanediol;
CAS Number	115-76-4;
PubChem CID	8284;
ChemSpider	7983;
UNII	A40PF8120T;
ChEBI	CHEBI:134759;
CompTox Dashboard (EPA)	DTXSID50150923 ;
ECHA InfoCard	100.003.731
Chemical and physical data
Formula	C7H16O2
Molar mass	132.203 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	59–62 °C (138–144 °F)
	SMILES CCC(CC)(CO)CO;
	InChI 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]

Synthesis

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

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ McKusick, B. (1948). "New Compounds. New Compounds as Insect Repellents". Journal of the American Chemical Society. 70 (5): 1982–1983. doi:10.1021/ja01185a602.

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[pmid18134033-1] 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.

[pmid13035673-2] 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.

[pmid13163224-3] 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.

[pmid13870189-4] 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.

[pmid23924275-6] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

Synthesis

See also

References