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Alprazolam Xanax

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Alprazolam Xanax manufacturers

Alprazolam Xanax Basic information
Product Name:Alprazolam Xanax
Synonyms:alprazolam--dea schedule iv item;ALPRAZOLAM BENZODIAZEPINE ANXIOL;ALPRAZOLAM CONTROLLED SUBSTANCE EPA(CRM STANDARD);ALPRAZOLAM UNLABELED 1000 UG/ML IN METHANOL;Cassadan;Esparon;ALPRAZOLAM USP C IV;ALPRAZOLAM,USP
CAS:28981-97-7
MF:C17H13ClN4
MW:308.76
EINECS:249-349-2
Product Categories:Aromatics;Heterocycles;Active Pharmaceutical Ingredients;API;Intermediates & Fine Chemicals;Pharmaceuticals;pharmaceutical intermediate;pharmaceutical intermediate and chemical research product
Mol File:28981-97-7.mol
Alprazolam Xanax Structure
Alprazolam Xanax Chemical Properties
Melting point 228-228.50C
Boiling point 463.51°C (rough estimate)
density 1.2000 (rough estimate)
refractive index 1.6110 (estimate)
Fp 11 °C
storage temp. 2-8°C
solubility H2O: insoluble
pka2.37±0.40(Predicted)
Water Solubility 70mg/L(ambient temperature)
BCS Class1
Major Applicationpharmaceutical (small molecule)
InChI1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3
InChIKeyVREFGVBLTWBCJP-UHFFFAOYSA-N
SMILESCc1nnc2CN=C(c3ccccc3)c4cc(Cl)ccc4-n12
CAS DataBase Reference28981-97-7(CAS DataBase Reference)
NIST Chemistry ReferenceAlprazolam(28981-97-7)
EPA Substance Registry SystemAlprazolam (28981-97-7)
Safety Information
Hazard Codes Xn,T,F
Risk Statements 22-39/23/24/25-23/24/25-11
Safety Statements 36-45-36/37-16-7
RIDADR 3249
WGK Germany 3
RTECS XZ5473000
HazardClass 6.1(b)
PackingGroup III
HS Code 2933910000
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Hazardous Substances Data28981-97-7(Hazardous Substances Data)
ToxicityLD50 in mice, rats (mg/kg): 1020, >2000 orally; 540, 610 i.p. (Nakajima)
DEA Controlled SubstancesCSCN: 2882
CAS SCH: Ⅳ
NARC: N
MSDS Information
ProviderLanguage
Alprazolam English
SigmaAldrich English
Alprazolam Xanax Usage And Synthesis
DescriptionAlprazolam (Item No. 14255) is an analytical reference material categorized as a benzodiazepine. Alprazolam is regulated as a Schedule IV compound in the United States. This product is intended for research and forensic applications.
Chemical PropertiesWhite Crystalline Solid
OriginatorXanax ,Upjohn ,US ,1981
UsesControlled substance (depressant). Anxiolytic
UsesAtorvastatin metabolite
DefinitionChEBI: A member of the class of triazolobenzodiazepines that is 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine carrying methyl, phenyl and chloro substituents at positions 1, 6 and 8 respectively. Alprazolam is only found in individu ls that have taken this drug.
Manufacturing Process6-Chloro-2-hydrazino-4-phenylquinoline: A stirred mixture of 2,6-dichloro-4- phenylquinoline (2.7 g, 0.01 mol) and hydrazine hydrate (6.8 g) was refluxed under nitrogen for 1 hour and concentrated in vacuum. The residue was suspended in warm water, and the solid was collected by filtration, dried and recrystallized from ethyl acetate-Skelly B hexanes to give 1.81 g (67% yield) of 6-chloro-2-hydrazino-4-phenylquinoline of melting point 156.5-157°C. 7-Chloro-1-methyl-5-phenyl-s-trizolo[4,3-a]quinoline: A stirred mixture of 6- chloro-2-hydrazino-4-phenylquinoline (1.4 g, 0.0052 mol), triethylorthoacetate (0.925 g, 0.0057 mol) and xylene (100 ml) was refluxed, under nitrogen, for 2 hours 40 minutes. During this period the ethanol formed in the reaction was removed by distillation through a short, glass helix-packed column. The mixture was concentrated to dryness in vacuum and the residue was crystallized from methanol-ethyl acetate to give: 1.28 g of 7-chloro-1- methyl-5-phenyl-s-triazolo[4,3-a]quinoline (83.9% yield). The analytical sample was crystallized from methylene chloride:methanol and had a melting point 252.5-253.5°C.
5-Chloro-2-(3-methyl-4H-1,2,4-triazol-4-yl)benzophenone (Oxidation of 7- chloro-1-methyl-5-phenyl-s-trizolo[4,3-a]quinoline): A stirred suspension of 7- chloro-1-methyl-5-phenyl-s-triazolo[4,3-a] quinoline (2,94 g, 0.01 mol) in acetone (110 ml) was cooled in an ice-bath and treated slowly with a solution prepared by adding sodium periodate (2 g) to a stirred suspension of ruthenium dioxide (200 mg) in water (35 ml). The mixture became dark. Additional sodium periodate (8 g) was added during the next 15 minutes. The ice-bath was removed and the mixture was stirred for 45 minutes. Additional sodium periodate (4 g) was added and the mixture was stirred at ambient temperature for 18 hours and filtered. The solid was washed with acetone and the combined filtrate was concentrated in vacuum. The residue was suspended in water and extracted with methylene chloride. The extract was dried over anhydrous potassium carbonate and concentrated. The residue was chromatographed on silica gel (100 g) with 10% methanol and 90% ethyl acetate; 50 ml fractions were collected. The product was eluted in fractions 10-20 and was crystallized from ethyl acetate to give: 0.405 g of melting point 168-169.5°C and 0.291 g of melting point 167.5-169°C (23.4% yield) of 5-chloro-2-(3-methyl-4H-1,2,4-triazol-4-yl)benzophenone. The analytical sample had a melting point of 168°C.
5-Chloro-2-[3-(hydroxymethyl)-5-methyl-4H-1,2,4-triazol-4-yl]benzophenone: A stirred mixture of 5-chloro-2-(3-methyl-4H-1,2,4-triazolo-4- yl)benzophenone, (2.98 g, 0.01 mol) paraformaldehyde (3 g) and xylene (100 ml) was warmed under nitrogen, in a bath maintained at 125°C for 7 hours. The mixture was then concentrated in vacuum. The residue was chromatographed on silica gel (150 g) with 3% methanol-97% chloroform. Fifty ml fractions were collected. The product was eluted in fractions 20-44. The fractions were concentrated and the residue was crystallized from ethanol-ethyl acetate to give: 1.64 g of melting point 138-142°C; 0.316 g of melting point 138.5-141°C; 0.431 g of melting point 139-141°C (72.8% yield) of 5-chloro-2-[3-(hydroxymethyl)-5-methyl-4H-1,2,4-triazol-4- yl]benzophenone. The analytical sample had a melting point of 138-139°C. 5-Chloro-2-[3-(bromomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]-benzophenone: A solution of 5-chloro-2-[3-(hydroxymethyl)-5-methyl-4H-1,2,4-triazol-4-yl]- benzophenone (328 mg, 0.001 mol) in dry, hydrocarbon-stabilized chloroform (5 ml) was cooled in an ice-bath and treated with phosphorus tribromide (0.1 ml). The colorless solution was kept in the ice-bath for 55 minutes, at ambient temperature (22-24°C), for 5 hours. The resulting yellow solution was poured into a mixture of ice and dilute sodium bicarbonate. This mixture was extracted with chloroform. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was crystallized from methylene chloride-ethyl acetate to give: 0.285 g of melting point 200- 240°C (decomposition) and 0.030 g of melting point 200-220°C (decomposition) of 5-chloro-2-[3-(bromomethyl)-5-methyl-4H-1,2,4-triazol-4- yl]benzophenone. The analytical sample had a melting point of 200-240°C.
8-Chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine: A stirred suspension of 5-chloro-2-[3-(bromomethyl)-5-methyl-4H-1,2,4-triazol- 4-yl]-benzophenone (391 mg, 0.001 mol) in tetrahydrofuran (15 ml) was cooled in an ice-bath and treated with a saturated solution of ammonia in methanol (12.5 ml). The resulting solution was allowed to warm to ambient temperature and stand for 24 hours. It was then concentrated in vacuum. The residue was suspended in water, treated with a little sodium bicarbonate and extracted with methylene chloride. The extract was washed with brine, dried with anhydrous potassium carbonate and concentrated. The residue was crystallized from methylene chloride-ethyl acetate to give 0.220 g of crude product of melting point 227-228.5°C. Recrystallization of this material from ethyl acetate gave 0.142 g of melting point 228-229.5°C of 8-chloro-1- methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine.
Brand nameNiravam (Schwarz Pharma); Xanax (Pharmacia & Upjohn).
Therapeutic FunctionTranquilizer
General DescriptionAlprazolam, 8-chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine (Xanax), israpidly absorbed from the GI tract. Protein binding is lower(~70%) than with most benzodiazepines because of itslower lipophilicity.α-Hydroxylation of the methyl group tothe methyl alcohol (a reaction analogous to benzylic hydroxylation)followed by conjugation is rapid; consequently,the duration of action is short. The drug is a highlypotent anxiolytic on a milligram basis.
References[1] MD J Y P, PHD  Pil W P M  Kyoung Ah Kim PhD, PHD, et al. Effect of CYP3A5*3 genotype on the pharmacokinetics and pharmacodynamics of alprazolam in healthy subjects[J]. Clinical Pharmacology & Therapeutics, 2006, 79 6: 590-599. DOI: 10.1016/j.clpt.2006.02.008
Tag:Alprazolam Xanax(28981-97-7) Related Product Information
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