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 NaCN are reacted together to give the corresponding cyanohydrin (cf Strecker synthesis), CID:12439573. The cyano group is then hydrated in acid to the corresponding amide, p-chloroatrolactamide, CID:15255544 (4). The amide group is then further hydrolyzed with a 2nd equivalent of water in concentrated lye to p-chloroatrolactic acid, (5). Esterification to Ethyl p-chloroatrolactate (6). Finally, nucleophilic addition a couple of equivalents of MeMgI are added to the ester give Phenaglycodol (7) crystals.

A mixed Pinacol coupling rxn between 4-chloroacetophenone and acetone with magnesium activated with a small amount of trimethylsilyl chloride gave a 40% yield of phenglycodol.

Notes

See "Novel trifluoromethyl derivatives of substituted diols" U.S. patent 3,134,819 also.
A Pinacol rearrangement occurs in acidic water:^[10]

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.
^ Jack Mills "2-chlorophenyl-3-methyl-2, 3-butanediols" U.S. patent 2,812,363 (1957 to Eli Lilly Co.)
^ GB 788896, Mills, Jack, "Improvements in or relating to novel substituted butanediol", published 1958-01-08, assigned to Eli Lilly & Co.
^ Maekawa, Hirofumi; Yamamoto, Yoshimasa; Shimada, Hisashi; Yonemura, Kazuaki; Nishiguchi, Ikuzo (2004). "Mg-promoted mixed pinacol coupling". Tetrahedron Letters. 45 (20): 3869–3872. doi:10.1016/j.tetlet.2004.03.109.
^ Murphy, Hubert W. (1964). "Pinacol Rearrangement of Phenaglycodol I". Journal of Pharmaceutical Sciences. 53 (3): 298–301. doi:10.1002/jps.2600530311.

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[1] 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.

[UsdinEfron1972-2] 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.

[Vida2013-3] Vida J (19 July 2013). Anticonvulsants. Elsevier. pp. 578–. ISBN 978-0-323-14395-0.

[HaddadWinchester1983-4] Haddad LM, Winchester JF (1983). Clinical Management of Poisoning and Drug Overdose. Saunders. ISBN 978-0-7216-4447-9.

[Drill1958-5] Drill VA (1958). Pharmacology in Medicine: A Collaborative Textbook. McGraw-Hill.

[Beckman1961-6] Beckman H (1961). Pharmacology; the nature, action and use of drugs. Saunders.

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

[8] GB 788896, Mills, Jack, "Improvements in or relating to novel substituted butanediol", published 1958-01-08, assigned to Eli Lilly & Co.

[9] Maekawa, Hirofumi; Yamamoto, Yoshimasa; Shimada, Hisashi; Yonemura, Kazuaki; Nishiguchi, Ikuzo (2004). "Mg-promoted mixed pinacol coupling". Tetrahedron Letters. 45 (20): 3869–3872. doi:10.1016/j.tetlet.2004.03.109.

[10] Murphy, Hubert W. (1964). "Pinacol Rearrangement of Phenaglycodol I". Journal of Pharmaceutical Sciences. 53 (3): 298–301. doi:10.1002/jps.2600530311.

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v t e Anxiolytics (N05B)
5-HT_1ARTooltip 5-HT1A receptor agonists	Buspirone Gepirone Tandospirone
GABA_ARTooltip GABAA receptor PAMsTooltip positive allosteric modulators	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Carisoprodol Chlormezanone^‡ Ethanol (alcohol) Etifoxine
Hypnotics	Zopiclone
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., escitalopram) SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (e.g., duloxetine) SARIsTooltip Serotonin antagonist and reuptake inhibitors (e.g., trazodone) TCAsTooltip Tricyclic antidepressants (e.g., clomipramine^#) TeCAsTooltip Tetracyclic antidepressants (e.g., mirtazapine) MAOIsTooltip Monoamine oxidase inhibitors (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Antipsychotics	Quetiapine Flupentixol
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Clinical data

ATC code	None
Legal status
Legal status	BR: Class C1 (Other controlled substances)^[1]
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

Synthesis

Notes

See also

References