28910-91-0

Usage

Uses

Used in Illicit Drug Market:
Flualprazolam is used as a designer drug for its sedative/hypnotic effects, particularly in the United States. It is generally abused by young adults, especially males, and is often compared to clonazepam and alprazolam in terms of its effects.
Used in Recreational Substances:
Flualprazolam is used as a recreational substance, primarily in the United States, where it is abused for its sedative and anxiolytic properties.
Used in Research and Forensic Applications:
Flualprazolam is used as an analytical reference material for research and forensic applications, given its structural similarity to other benzodiazepines and its tranquilizing effects.
Biotechnological Applications:
Flualprazolam, as a 2′-fluoro derivative of alprazolam, has been sold as a designer drug on the illicit drug market. It is part of the triazolobenzodiazepine class, which are benzodiazepines fused with a triazole ring, and has similar sedative and anxiolytic effects to other drugs in its class.

Shipping

Room Temperature in continental US; may vary elsewhere.

Forms and nomenclature

A neat solid.

Mode of action

Flualprazolam is an agonist at thebenzodiazepine siteof the gamma-aminobutyric acid (GABAA) receptor. Its pharmacological effects are similar to those of other benzodiazepines, such as alprazolam，which is currently controlled under the Convention on Psychotropic Substances of 1971.User reports have indicated that flualprazolam depresses central nervous system function, with effects such as sedation, loss of memory and disinhibition,similar to other benzodiazepines.

Regulatory Status

Flualprazolam is banned in Sweden, also is illegal in the UK. In December 2019, the World Health Organization recommended flualprazolam for international scheduling as a Schedule IV medication under the Convention on Psychotropic Substances.

Synthetic route

acetic acid hydrazide (1068-57-1) + 7-chloro-5-(2-fluorophenyl)-2-(N-nitrosomethylamino)-3H-1,4-benzodiazepine (59467-62-8) → flualprazolam (28910-91-0)

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 120℃; for 1h;	84%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 120℃; for 4h;	280 mg

acetic acid hydrazide (1068-57-1) + 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-1,4-benzodiazepin-2(2H)-one (2886-65-9) → flualprazolam (28910-91-0)

Conditions	Yield
In butan-1-ol at 125℃; for 8h; Temperature; Solvent;	81.2%

7-chloro-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepine-2-thione (1645-32-5) → flualprazolam (28910-91-0)

Conditions	Yield
In dichloromethane; water; butan-1-ol

7-chloro-5-(2-fluorophenyl)-1,3-dihydro-1,4-benzodiazepin-2(2H)-one (2886-65-9) → flualprazolam (28910-91-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: titanium tetrachloride / tetrahydrofuran / 5.33 h / -5 - 45 °C / Inert atmosphere 2: acetic acid; sodium nitrite / water / 3.25 h / 3 - 25 °C 3: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 4 h / 120 °C View Scheme

Upstream product

• 1068-57-1 acetic acid hydrazide 
• 2886-65-9 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-1,4-benzodiazepin-2(2H)-one 
• 1645-32-5 7-chloro-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepine-2-thione 
• 59467-62-8 7-chloro-5-(2-fluorophenyl)-2-(N-nitrosomethylamino)-3H-1,4-benzodiazepine 

Relevant academic research and scientific papers

Preparation method of flualprazolam

The invention discloses a preparation method of flualprazolam, and relates to the technical field of medicine synthesis. The preparation method of the flualprazolam comprises the following steps: by taking phosphorus pentasulfide as a vulcanizing reagent, vulcanizing carbonyl groups of 7-chloro-1,3-dihydro-5-(2-fluorophenyl)-3H-1,4-benzodiazepine-2-one to obtain an intermediate; and adding the intermediate and acethydrazide into an organic solvent, and reacting to obtain flualprazolam. The synthesis method provided by the invention only needs two steps and is simple to operate, so the reactiontime is greatly shortened, the reaction cost is reduced, and the reaction efficiency is improved; and the reaction process conditions are mild, and the reagent toxicity is low, so the synthesis process is safe and environment-friendly.

8-chloro-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolbenzo[1,4]benzodiazepine for forensic science, preparation method therefor and application of 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolbenzo[1,4]benzodiazepine

The invention discloses 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolbenzo[1,4]benzodiazepine with a structure represented by a formula shown in the description. A preparation method for the8-chloro-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolbenzo[1,4]benzodiazepine comprises the following steps: (1) synthesizing a compound B from a compound A; (2) synthesizing a compound C from the compound B; and (3) synthesizing the 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolbenzo[1,4]benzodiazepine compound D from the compound C. Shown by application researches on the 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolbenzo[1,4]benzodiazepine, the prepared 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolbenzo[1,4]benzodiazepine can be applied to reference materials for detection and identification work of organs of public security. The technical scheme of the invention achieves the following beneficial technical effects that an optimal synthesis route for synthesizing the 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolbenzo[1,4]benzodiazepine is optimized; the target object, i.e., the 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolbenzo[1,4]benzodiazepine is separated and purified, and thus, the purity of the 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolbenzo[1,4]benzodiazepine reaches 99% or more; and the prepared 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolbenzo[1,4]benzodiazepine can directly serve as a reference substance for the detection and identification work of the organs of public security.

1,4-Benzodiazepine N-nitrosoamidines: Useful intermediates in the synthesis of tricyclic benzodiazepines

1,4-Benzodiazepine N-nitrosoamidines have been used as scaffolds for the preparation of different tricyclic derivatives. Replacement of the N-nitrosoamidine moiety through treatment with the nucleophiles acetylhydrazine, aminoacetaldehyde dimethylacetal and 1-amino-2-propanol, followed by an acid-catalyzed cyclization step, afforded triazolo and imidazobenzodiazepines 1, 6, and 7, respectively, in good yields. When acetylhydrazine is used as a nucleophile, the overall process provides an alternative route to alprazolam (1b) and triazolam (1c), respectively.

Certain PAF antagonist/antihistamine combinations and methods

Methods and compositions are disclosed employing combinations of antihistamines with certain diaryl tetrahydrofuran, diaryl tetrahydrothiophene, triazolobenzodiazepine or thienotriazolodiazepine PAF--antagonist compounds in the treatment of allergic reactions.

Animal feed and process

An animal feed comprising a compound of the group consisting of 6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula: STR1 WHEREIN R is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, phenyl, benzyl and -COOR' in which R' is alkyl of 1 to 4 carbon atoms, inclusive; wherein R1 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; and wherein R2, R3, R4 and R5 are selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkanoylamino and dialkylamino in which the carbon chain moieties are of 1 to 3 carbon atom, inclusive and their pharmacologically acceptable acid addition salts in combination with a nutrient feed. A process for obtaining increased productivity in meat producing, milk producing, and egg laying animals by feeding the aforementioned compounds in combination with nutrient feeds.

6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines

6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula (IV): SPC1 wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, phenyl, benzyl and -COOR' in which R' is alkyl of 1 to 4 carbon atoms, inclusive; wherein R1 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; and wherein R2, R3, R4 and R5 are selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkanoylamino and dialkylamino in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive, are produced by condensing a 1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione of the formula (I): SPC2 wherein R1, R2, R3, R4 and R5 are defined as above, with an organic acid hydrazide of the formula: EQU1 wherein R is defined as above. The new products of formula IV including their pharmacologically acceptable acid addition salts are useful as sedatives, tranquilizers and muscle relaxants in mammals and birds.