Phenaglycodol

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]

Phenaglycodol
Clinical data
ATC code
  • None
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.001.124
Chemical and physical data
FormulaC11H15ClO2
Molar mass214.69 g·mol−1
3D model (JSmol)

Synthesis
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.
  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.


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