Alprazolam was first synthesized by Upjohn (now a part of Pfizer). It is covered under U.S. Patent 3,987,052, which was filed on October 29, 1969, granted on October 19, 1976 and expired in September 1993. Alprazolam was released in 1981.The first approved indication was panic disorder. Upjohn took this direction at the behest of a young psychiatrist David Sheehan. Sheehan's suggestion was to use the new distinction the DSM-III created in the classification of anxiety disorders between generalized anxiety disorder (GAD) and panic disorder in order to market alprazolam specifically for the latter.
Alprazolam has an exceptional history insofar as soon after its introduction a large number of case reports were published in the medical literature of severe withdrawal symptom-related case reports of psychoses, seizures, and intense rebound anxiety upon discontinuation of alprazolam.

The IUPAC name of Alprazolam is 8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine. With the CAS registry number 28981-97-7, it is also named as 4H-(1,2,4)Triazolo(4,3-alpha)(1,4)benzodiazepine, 8-chloro-1-methyl-6-phenyl-. The product's categories are Active Pharmaceutical Ingredients; API; Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is white crystalline solid, which should be stored in sealed place at 2-8 °C. In addition, this chemical is insoluble in water.

The other characteristics of this product can be summarized as: (1)EINECS: 249-349-2; (2)ACD/LogP: 1.92; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 1.915; (5)ACD/LogD (pH 7.4): 1.916; (6)ACD/BCF (pH 5.5): 16.795; (7)ACD/BCF (pH 7.4): 16.827; (8)ACD/KOC (pH 5.5): 262.036; (9)ACD/KOC (pH 7.4): 262.532; (10)H bond acceptors: 4; (11)H bond donors: 0; (12)Freely Rotating Bonds: 1; (13)Index of Refraction: 1.711; (14)Molar Refractivity: 88.229 cm³; (15)Molar Volume: 225.579 cm³; (16)Surface Tension: 52.178 dyne/cm; (17)Density: 1.369 g/cm³; (18)Flash Point: 261.609 °C; (19)Melting Point:228-228.5 °C; (20)Enthalpy of Vaporization: 77.94 kJ/mol; (21)Boiling Point: 508.959 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Alprazolam: this chemical can be prepared by 2-(3-Bromomethyl-5-methyl-[1,2,4]triazol-4-yl)-5-chloro-benzophenone.



This reaction needs NH₃ and CH₂Cl₂ at temperature of -50 °C by reflux. The reaction time is 5 hours. The yield is 83.3 %.

Uses of Alprazolam: this chemical is primarily used to treat moderate to severe anxiety disorders and panic attacks, and is used as an adjunctive treatment for anxiety associated with moderate depression. It is available in an instant release and an extended-release preparation, both of which are available under several generic names. Alprazolam possesses anxiolytic, sedative, hypnotic, anticonvulsant, and muscle relaxant properties. Furthermore, it can react with Carbonic acid diethyl ester to get 8-Chloro-1-methyl-6-phenyl-4H-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine-4-carboxylic acid ethyl ester.



This reaction needs NaH and Ethanol by heating for 1.5 hours. The yield is 56 %.

When you are using this chemical, please be cautious about it as the following: it is highly flammable. Please keep away from sources of ignition. It is also harmful if swallowed and toxic by inhalation, in contact with skin and if swallowed. Moreover, it is danger of very serious irreversible effects. You should wear suitable protective clothing and gloves. And in case of accident or if you feel unwell, please seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)SMILES:Cc1nnc2n1-c3ccc(cc3C(=NC2)c4ccccc4)Cl
(2)InChI:InChI=1/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
(3)InChIKey:VREFGVBLTWBCJP-UHFFFAOYAT
(4)Std. InChI:InChI=1S/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
(5)Std. InChIKey:VREFGVBLTWBCJP-UHFFFAOYSA-N

The toxicity data is as follows: