Prenderol

{{short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 2,2-diethyl-1,3-propanediol

| image = Prenderol.svg

| image_class = skin-invert-image

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| excretion =

| CAS_number = 115-76-4

| ATC_prefix =

| ATC_suffix =

| PubChem = 8284

| ChemSpiderID = 7983

| UNII = A40PF8120T

| ChEBI = 134759

| C=7 | H=16 | O=2

| smiles = CCC(CC)(CO)CO

| StdInChI = 1S/C7H16O2/c1-3-7(4-2,5-8)6-9/h8-9H,3-6H2,1-2H3

| StdInChIKey = XRVCFZPJAHWYTB-UHFFFAOYSA-N

| melting_point = 59-62

}}

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.{{cite journal | vauthors = Berger FM | title = Anticonvulsant action of 2-substituted-1,3-propanediols | journal = Proceedings of the Society for Experimental Biology and Medicine | location = New York, N.Y. | volume = 71 | issue = 2 | pages = 270–271 | date = June 1949 | pmid = 18134033 | doi = 10.3181/00379727-71-17159 | s2cid = 32255832 }}{{cite journal | vauthors = Funderburk WH, Unna KR | title = Site of action of 2, 2-diethyl-1,3-propanediol (prenderol) on the central nervous system | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 107 | issue = 3 | pages = 344–55 | date = March 1953 | pmid = 13035673 | url = https://jpet.aspetjournals.org/content/107/3/344.short }}{{cite journal | vauthors = Mailer AB | title = Effects of mephenesin and prenderol on intellectual functions of mental patients | journal = Journal of Clinical Psychology | volume = 10 | issue = 3 | pages = 283–5 | date = July 1954 | pmid = 13163224 | doi = 10.1002/1097-4679(195407)10:3<283::aid-jclp2270100322>3.0.co;2-a }}{{cite journal | vauthors = Blum B | title = Head shaking and nystagmus produced by 2,2-diethyl, 1,3-propanediol (prenderol) in the rat | journal = Archives Internationales de Pharmacodynamie et de Therapie | volume = 137 | pages = 128–36 | date = May 1962 | 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.{{cite journal | vauthors = Wang G, Lu Q | title = A nitrate ester of sedative alkyl alcohol improves muscle function and structure in a murine model of Duchenne muscular dystrophy | journal = Molecular Pharmaceutics | volume = 10 | issue = 10 | pages = 3862–70 | date = October 2013 | pmid = 23924275 | doi = 10.1021/mp400310r }}

Synthesis

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

prenderol.{{cite journal |doi=10.1021/ja01185a602 |title=New Compounds. New Compounds as Insect Repellents |date=1948 |last1=McKusick |first1=B. |journal=Journal of the American Chemical Society |volume=70 |issue=5 |pages=1982–1983 }}

See also

References

{{Reflist}}

{{Alcohols}}

{{Sedatives}}

Category:Alkanediols

Category:Muscle relaxants

{{musculoskeletal-drug-stub}}