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Phenaglycodol

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Chemical compound

Pharmaceutical compound

Phenaglycodol
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
PubChemCID	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 namesAcalmid,Acalo,Alterton,Atadiol,Felixyn,Neotran,Pausital,Remin,Sedapsin,Sinforil,Stesil,Ultran)^[2] is adrug described as atranquilizer orsedative which hasanxiolytic andanticonvulsant properties.^[3]^[4] It is relatedpharmacologically tomeprobamate, though it is not acarbamate.^[5]^[6]

Synthesis

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p-Chloroacetophenone andpotassium cyanide (KCN) are reacted together via aStrecker reaction to give the correspondingcyanohydrin (3). The cyano group is thenhydrated 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 givep-chloroatrolactic acid (5). Esterification then provides ethylp-chloroatrolactate (6). Finally,nucleophilic addition with methylmagnesium iodide give phenaglycodol (7) crystals.^[7]^[8]

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

References

[edit]

^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. Retrieved2023-08-16.
^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 toEli Lilly Co.
^GB 788896, Mills J, "Improvements in or relating to novel substituted butanediol", published 1958-01-08, assigned toEli 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.

US 3134819, Maxwell G, Pachter IJ, "Novel trifluoromethyl derivatives of substituted diols", issued 26 May 1964, assigned to Smith Kline and French Laboratories Ltd
Murphy HW (March 1964). "Pinacol Rearrangement of Phenaglycodol I. Characterization of Products Produced".Journal of Pharmaceutical Sciences.53:298–301.doi:10.1002/jps.2600530311.PMID 14185017.

v t e Anxiolytics (N05B)
5-HT_1ARTooltip 5-HT1A receptoragonists	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
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
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g.,prazosin) Alpha-2 agonists (e.g.,clonidine,dexmedetomidine,guanfacine) Beta blockers (e.g.,propranolol,atenolol,betaxolol,nadolol,oxprenolol,pindolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine (tobacco) Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Hypnotics/sedatives (N05C)

GABA_A

Alcohols	2M2B Chloralodol Ethanol (alcohol) Diethylpropanediol Ethchlorvynol Methylpentynol Trichloroethanol
Barbiturates	Allobarbital Amobarbital Aprobarbital Barbital Butabarbital Butobarbital Cyclobarbital Ethallobarbital Heptabarb Hexobarbital Mephobarbital Methohexital Narcobarbital Pentobarbital Phenallymal Phenobarbital Propylbarbital Proxibarbal Reposal Secobarbital Talbutal Thiamylal Thiopental Thiotetrabarbital Vinbarbital Vinylbital
Benzodiazepines	Brotizolam Cinolazepam Climazolam Clonazolam Doxefazepam Estazolam Flubromazolam Flunitrazolam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Loprazolam Lormetazepam Midazolam Nimetazepam Nitemazepam Nitrazepam Nitrazolam Quazepam Temazepam Triazolam
Carbamates	Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate
Imidazoles	Etomidate Metomidate Propoxate
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Capuride Carbromal Ectylurea
Neurosteroids	Acebrochol Alfadolone Alfaxolone Brexanolone (allopregnanolone) Eltanolone (pregnanolone) Ganaxolone Hydroxydione Minaxolone Progesterone Renanolone Zuranolone
Nonbenzodiazepines	Eszopiclone Indiplon Lirequinil Necopidem Pagoclone Pazinaclone Saripidem Suproclone Suriclone Zaleplon Zolpidem Zopiclone
Phenols	Cipepofol (ciprofol) Fospropofol Propofol Propofol hemisuccinate
Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Others	Acetophenone Acetylglycinamide chloral hydrate Bromide compounds Lithium bromide Potassium bromide Sodium bromide Centalun Chloral betaine Chloral hydrate Chloralose Clomethiazole Dichloralphenazone Gaboxadol (THIP) Ibotenic acid (Amanita muscaria) Kavalactones Loreclezole Muscimol (Amanita muscaria) Paraldehyde Petrichloral Sesquiterpene Isovaleramide Isovaleric acid Valerenic acid Sulfonylalkanes Sulfonmethane (sulfonal) Tetronal Trional Triclofos

GABA_B

H₁

Antihistamines	Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Perlapine Pheniramine Promethazine Propiomazine
Antidepressants	Serotonin antagonists and reuptake inhibitors Etoperidone Nefazodone Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.

α₂-Adrenergic

5-HT_2A

Antidepressants	Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.
Others	Niaprazine