36505-84-7 Usage
Uses
Different sources of media describe the Uses of 36505-84-7 differently. You can refer to the following data:
1. Tranquilizer (minor).
2. Buspirone is an extremely specific drug that could possibly represent a new chemical class
of anxiolytics—azaspirones. As an anxiolytic, its activity is equal to that of benzodiazepines; however, it is devoid of anticonvulsant and muscle relaxant properties, which are
characteristic of benzodiazepines.
3. 5-Chloro Buspirone is an impurity of Buspirone Hydrochloride (B689850), a non-benzodiazepine anxiolytic and a 5-hydroxytryptamine (5-HT1) receptor agonist.
Definition
ChEBI: An azaspiro compound that is 8-azaspiro[4.5]decane-7,9-dione substituted at the nitrogen atom by a 4-(piperazin-1-yl)butyl group which in turn is substituted by a pyrimidin-2-yl group at the N4 position.
Brand name
Buspar (Bristol-Myers Squibb).
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.
General Description
The initial compound in this series, buspirone (BuSpar), hasanxiolytic and antidepressant activities and is a partial5-HT1A agonist. Its anxiolytic activity is reportedly causedby its ability to diminish 5-HT release (via 5-HT1A agonism).High short-term synaptic levels of 5-HT are characteristic ofanxiety. Also, because it is a partial agonist, it can stimulatepostsynaptic receptors when 5-HT levels are low in thesynapse, as is the case in depression. Several other spironesare in development as anxiolytics and antidepressants.
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.
Nucleophilic aromatic substitution reactions under aqueous, mild conditions using polymeric additive HPMC
Ansari, Tharique N.,Borlinghaus, Niginia,Braje, Leon H.,Braje, Wilfried M.,Handa, Sachin,Ogulu, Deborah,Wittmann, Valentin
supporting information, p. 3955 - 3962 (2021/06/17)
The use of the inexpensive, benign, and sustainable polymer, hydroxypropyl methylcellulose (HPMC), in water enables nucleophilic aromatic subsitution (SNAr) reactions between various nucleophiles and electrophiles. The mild reaction conditions facilitate a broad functional group tolerance that can be utilized for subsequent derivatization for the synthesis of pharmaceutically relevant building blocks. The use of only equimolar amounts of all reagents and water as reaction solvent reveals the greenness and sustainability of the methodology presented herein.
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.
