Phenaglycodol
Clinical data
ATC code
  • None
Identifiers
  • 2-(4-chlorophenyl)-3-methyl-2,3-butanediol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.001.124 Edit this at Wikidata
Chemical and physical data
FormulaC11H15ClO2
Molar mass214.69 g·mol−1
3D model (JSmol)
  • CC(C)(C(C)(c1ccc(cc1)Cl)O)O
  • InChI=1S/C11H15ClO2/c1-10(2,13)11(3,14)8-4-6-9(12)7-5-8/h4-7,13-14H,1-3H3
  • Key:HTYIXCKSEQQCJO-UHFFFAOYSA-N

Phenaglycodol (brand names Acalmid, Acalo, Alterton, Atadiol, Felixyn, Neotran, Pausital, Remin, Sedapsin, Sinforil, Stesil, Ultran)[1] is a drug described as a tranquilizer or sedative which has anxiolytic and anticonvulsant properties.[2][3] It is related structurally and pharmacologically to meprobamate, though it is not a carbamate.[4][5]

Synthesis

Jack Mills "2-chlorophenyl-3-methyl-2, 3-butanediols" U.S. Patent 2,812,363 (1957 to Eli Lilly Co.).
Jack Mills "2-chlorophenyl-3-methyl-2, 3-butanediols" U.S. Patent 2,812,363 (1957 to Eli Lilly Co.).

p-Chloroacetophenone and NaCN are reacted together to give the corresponding cyanohydrin (cf Strecker synthesis). The cyano group is then hydrated in acid to the corresponding amide, thus p-chloroatrolactamide (4) is formed. The amide group is then further hydrolyzed with a 2nd equivalent of water in concentrated lye to p-chloroatrolactic acid (5); this is then esterified to Ethyl p-chloroatrolactate (6). Finally, nucleophilic addition a couple of equivalents of MeMgI are added to the ester give Phenaglycodol (7) crystals.

Notes

See also

References

  1. ^ Usdin E, Efron DH, U.S. National Institute of Mental Health (1972). Psychotropic drugs and related compounds. National Institute of Mental Health; [for sale by the Supt. of Docs., U.S. Govt. Print. Off., Washington. ISBN 9780080255101.
  2. ^ Vida J (19 July 2013). Anticonvulsants. Elsevier. pp. 578–. ISBN 978-0-323-14395-0.
  3. ^ Haddad LM, Winchester JF (1983). Clinical Management of Poisoning and Drug Overdose. Saunders. ISBN 978-0-7216-4447-9.
  4. ^ Drill VA (1958). Pharmacology in Medicine: A Collaborative Textbook. McGraw-Hill.
  5. ^ Beckman H (1961). Pharmacology; the nature, action and use of drugs. Saunders.