36505-84-7 Usage
Description
Buspirone is a non-benzodiazepine anxiolytic drug that belongs to the chemical class of azaspirones. It is a highly specific compound that selectively acts as a 5-hydroxytryptamine (5-HT1) receptor agonist, providing anxiolytic effects without the sedative, muscle relaxant, or anticonvulsant properties associated with benzodiazepines.
Uses
Used in Pharmaceutical Industry:
Buspirone is used as a tranquilizer for the treatment of mild anxiety disorders. It is effective in reducing anxiety symptoms while avoiding the side effects commonly associated with benzodiazepines, such as sedation and dependence.
Used in Research and Development:
As a highly specific anxiolytic, Buspirone is used in research to study the role of 5-HT1 receptors in anxiety and other related disorders. This helps in the development of new drugs and therapies targeting these receptors for the treatment of anxiety and other mental health conditions.
Used in Impurity Testing:
5-Chloro Buspirone is an impurity of Buspirone Hydrochloride, a non-benzodiazepine anxiolytic. It is important to monitor and control the levels of this impurity in the final drug product to ensure safety, efficacy, and quality.
Biological Functions
Buspirone (BuSpar) is the first example of a class of
anxiolytic agents that can relieve some symptoms of
anxiety in doses that do not cause sedation. Buspirone
is structurally unrelated to existing psychotropic drugs.
Mechanism of action
Although buspirone has been shown to interact with a
number of neurotransmitter systems in the brain, it appears
that its clinically relevant effects are mediated
through interactions at the serotonin (5-hydroxytryptamine,
5-HT) 5-HT1A receptor, where it acts as a partial
agonist.
Pharmacology
Buspirone is as effective as the benzodiazepines in the
treatment of general anxiety. However, the full anxiolytic
effect of buspirone takes several weeks to develop,
whereas the anxiolytic effect of the benzodiazepines is
maximal after a few days of therapy. In therapeutic
doses, buspirone has little or no sedative effect and
lacks the muscle relaxant and anticonvulsant properties
of the benzodiazepines. In addition, buspirone does not
potentiate the central nervous system depression
caused by sedative–hypnotic drugs or by alcohol, and it
does not prevent the symptoms associated with benzodiazepine
withdrawal.
Clinical Use
Buspirone is effective in general anxiety and in anxiety
with depression.
Side effects
Like the benzodiazepines, buspirone appears to be safe
even when given in very high doses. The most common
side effects are dizziness, light-headedness, and headache.
Abuse, dependence, and withdrawal have not been
reported, and buspirone administration does not produce
any cross-tolerance to the benzodiazepines. Buspirone
has been reported to increase blood pressure in
patients taking monoamine oxidase inhibitors, and it
may increase plasma levels of haloperidol if coadministered
with that agent.
Synthesis
Buspirone, 8-[4-[4-(2-pyrimidyl)-1-piperazinyl]butyl]-8-azaspiro [4,5]
decan-7,9-dione (5.2.6), is synthesized by the reaction of 1-(2-pyrimidyl)-4-
(4-aminobutyl)piperazine (5.2.4) with 8-oxaspiro[4,5]decan-7,9-dione (5.2.5). In turn, 1-
(2-pyrimidyl)-4-(4-aminobutyl)piperazine (5.2.4) is synthesized by the reaction of
1-(2-pyrimidyl)piperazine with 4-chlorobutyronitrile, giving 4-(2-pyrimidyl)-1-(3-
cyanopropyl)piperazine (5.2.3), which is hydrogenated with Raney nickel into buspirone
(5.2.4) [51–55].
Metabolism
Buspirone is well absorbed from the gastrointestinal
tract, and peak blood levels are achieved in 1 to 1.5
hours; the drug is more than 95% bound to plasma proteins.
Buspirone is extensively metabolized, with less
than 1% of the parent drug excreted into the urine unchanged.
At least one of the metabolic products of buspirone
is biologically active. The parent drug has an
elimination half-life of 4 to 6 hours.
Check Digit Verification of cas no
The CAS Registry Mumber 36505-84-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,6,5,0 and 5 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 36505-84:
(7*3)+(6*6)+(5*5)+(4*0)+(3*5)+(2*8)+(1*4)=117
117 % 10 = 7
So 36505-84-7 is a valid CAS Registry Number.
InChI:InChI=1/C21H31N5O2/c27-18-16-21(6-1-2-7-21)17-19(28)26(18)11-4-3-10-24-12-14-25(15-13-24)20-22-8-5-9-23-20/h5,8-9H,1-4,6-7,10-17H2
36505-84-7Relevant articles and documents
Buspirone Analogues. 1. Structure-Activity Relationships in a Series of N-Aryl- and Heteroarylpiperazine Derivatives
Yevich, J. P.,Temple, D. L.,New, J. S.,Taylor, Duncan P.,Riblet, L. A.
, p. 194 - 203 (1983)
A series of analogues of buspirone was synthesized in which modifications were made in the aryl moiety, alkylene chain length, and cyclic imide portion of the molecule.These compounds were tested in vitro for their binding affinities to rat brain membrane sites labeled by either the dopamine antagonist spiperone or the α1-adrenergic antagonist WB-4101.Compounds were also tested in vivo for tranquilizing properties and induction of catalepsy.Potency at the spiperone binding site was affected by alkylene chain length and imide portion composition.Nonortho substituents on the aryl moiety had little effect on spiperone binding affinity.Structure-activity relationships of ortho substituents demonstrated only modest correlations between the receptor binding data and physical parameters of the substituents.The complex nature of the drug-receptor interactions may be understood in terms of the fit of buspirone to a hypothetical model of the dopamine receptor.
Large-steric-hindrance N-heterocyclic carbene palladium complex, preparation method and application thereof, and synthesis method of sonidegib based on large-steric-hindrance N-heterocyclic carbene palladium complex
-
Paragraph 0195; 0202-0204, (2021/01/24)
The invention belongs to the technical field of organic synthesis and chemical catalysis, and discloses a large-steric-hindrance N-heterocyclic carbene palladium complex, a preparation method thereof,an application of the complex in efficient catalysis of a C-N coupling reaction under a room-temperature air condition, and a synthesis method of sonidegib based on the complex. According to the large-steric-hindrance N-heterocyclic carbene palladium complex, diphenyl imidazole serves as a main ligand framework, functionalized allyl serves as an auxiliary ligand, the functionalized allyl is introduced beside a metal center of a catalyst to serve as an auxiliary ligand, the catalytic activity and stability are remarkably improved, the large-steric-hindrance N-heterocyclic carbene palladium complex can be applied to efficient catalysis of a CN coupling reaction, particularly, the CN coupling reaction can be efficiently catalyzed under the room temperature condition, and the yield can reachup to 99%. The invention also provides a method for synthesizing sonidegib by taking aryl/aliphatic amine and aryl chloride as reactants and a three-step method at room temperature under the catalysisof a palladium catalytic system, the synthetic method has few steps, and the total yield can reach 74.5%.
The design and preparation of metabolically protected new arylpiperazine 5-HT1A ligands
Tandon, Manish,O'Donnell, Mary-Margaret,Porte, Alex,Vensel, David,Yang, Donglai,Palma, Rocio,Beresford, Alan,Ashwell, Mark A.
, p. 1709 - 1712 (2007/10/03)
New arylpiperazines related to buspirone, gepirone and NAN-190 were designed and screened in silico for their 5-HT1A affinity and potential sites of metabolism by human cytochrome P450 (CYP3A4). Modifications to these structures were assessed in silico for their influence on both 5HT 1A affinity and metabolism. Selected new molecules were synthesized and purified in a parallel chemistry approach to determine structure activity relationships (SARs). The resulting molecules were assessed in vitro for their 5HT1A affinity and half-life in a heterologously expressed human CYP3A4 assay. Molecular features responsible for 5-HT1A affinity and CYP3A4 stability are described.