Phenaglycodol

Phenaglycodol
Clinical data
ATC code	None;
Legal status
Legal status	BR: Class C1 (Other controlled substances);
Identifiers
	IUPAC name 2-(4-chlorophenyl)-3-methyl-2,3-butanediol;
CAS Number	79-93-6;
PubChem CID	6617;
ChemSpider	6365;
UNII	LMQ31KU50K;
CompTox Dashboard (EPA)	DTXSID6023444 ;
ECHA InfoCard	100.001.124
Chemical and physical data
Formula	C11H15ClO2
Molar mass	214.69 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)(C(C)(c1ccc(cc1)Cl)O)O;
	InChI 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)^[2] is a drug described as a tranquilizer or sedative which has anxiolytic and anticonvulsant properties.^[3]^[4] It is related pharmacologically to meprobamate, though it is not a carbamate.^[5]^[6]

Synthesis

p-Chloroacetophenone and potassium cyanide (KCN) are reacted together via a Strecker reaction to give the corresponding cyanohydrin (3). The cyano group is then hydrated in acid to the corresponding amide, p-chloroatrolactamide (4). The amide group is then further hydrolyzed with a second equivalent of water in concentrated lye to give p-chloroatrolactic acid (5). Esterification then provides ethyl p-chloroatrolactate (6). Finally, nucleophilic addition with methylmagnesium iodide give phenaglycodol (7) crystals.^[7]^[8]

In a second method, a mixed pinacol coupling reaction between para-chloroacetophenone and acetone that was catalyzed by magnesium activated with a small amount of trimethylsilyl chloride gave a 40% yield of phenglycodol.^[9]

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ 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.
^ Vida J (19 July 2013). Anticonvulsants. Elsevier. pp. 578–. ISBN 978-0-323-14395-0.
^ Haddad LM, Winchester JF (1983). Clinical Management of Poisoning and Drug Overdose. Saunders. ISBN 978-0-7216-4447-9.
^ Drill VA (1958). Pharmacology in Medicine: A Collaborative Textbook. McGraw-Hill.
^ Beckman H (1961). Pharmacology; the nature, action and use of drugs. Saunders.
^ US 2812363, Mills J, "2-Chlorophenyl-3-methyl-2,3-butanediols", issued 5 November 1957, assigned to Eli Lilly Co.
^ GB 788896, Mills J, "Improvements in or relating to novel substituted butanediol", published 1958-01-08, assigned to Eli Lilly & Co.
^ Maekawa H, Yamamoto Y, Shimada H, Yonemura K, Nishiguchi I (2004). "Mg-promoted mixed pinacol coupling". Tetrahedron Letters. 45 (20): 3869–3872. doi:10.1016/j.tetlet.2004.03.109.

Phenaglycodol

Synthesis

See also

References

Further reading

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