Product Name

  • Name

    Buspirone

  • EINECS 253-072-2
  • CAS No. 36505-84-7
  • Article Data15
  • CAS DataBase
  • Density 1.24g/cm3
  • Solubility
  • Melting Point 2-8°C
  • Formula C21H31N5O2
  • Boiling Point 613.9 °C at 760 mmHg
  • Molecular Weight 385.509
  • Flash Point 325.1 °C
  • Transport Information UN 2811 6
  • Appearance white
  • Safety 45
  • Risk Codes 25
  • Molecular Structure Molecular Structure of 36505-84-7 (Buspirone)
  • Hazard Symbols ToxicT
  • Synonyms Buspin;Buspirone;Buspironum;8-Azaspiro(4,5)decane-7,9-dione, 8-(4-(4-(2-pyrimidinyl)piperizinyl)butyl)-;
  • PSA
  • LogP

Synthetic route

1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

N-(2-pyridinyl)piperazine
20980-22-7

N-(2-pyridinyl)piperazine

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
With potassium carbonate; benzyltriethylammonium bromide Product distribution; 1.) xylene, reflux, 3 h, 2.) reflux, 5 h; other imides and catalysts, variation of reaction time, also in toluene; also 1-(2-quinolinyl)piperazine;97%
With potassium carbonate; benzyltriethylammonium bromide 1.) xylene, reflux, 3 h, 2.) reflux, 5 h; Yield given. Multistep reaction;
...Expand
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

8-(4-(piperazin-1-yl)butyl)-8-azaspiro[4.5]decane-7,9-dione
80827-59-4

8-(4-(piperazin-1-yl)butyl)-8-azaspiro[4.5]decane-7,9-dione

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
With C48H55ClN2Pd; sodium t-butanolate In 1,2-dimethoxyethane at 20℃; for 16h; Inert atmosphere; Sealed tube;90%
3,3-tetramethylene glutaric anhydride
5662-95-3

3,3-tetramethylene glutaric anhydride

1-(pyrimidin-2-yl)-4-(4-aminobutyl)piperazine
33386-20-8

1-(pyrimidin-2-yl)-4-(4-aminobutyl)piperazine

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
In toluene for 10h; Heating;78%
8-(4-hydroxybutyl)-8-azaspiro[4.5]decane-7,9-dione
21098-10-2

8-(4-hydroxybutyl)-8-azaspiro[4.5]decane-7,9-dione

N-(2-pyridinyl)piperazine
20980-22-7

N-(2-pyridinyl)piperazine

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
With [RhCl2(p-cymene)]2; bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran at 250℃; under 37503.8 Torr; Flow reactor;76%
N-(2-pyridinyl)piperazine
20980-22-7

N-(2-pyridinyl)piperazine

8-(4-bromobutyl)-8-azaspiro[4.5]decane-7,9-dione
80827-62-9

8-(4-bromobutyl)-8-azaspiro[4.5]decane-7,9-dione

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 12h; Heating;71.4%
With potassium carbonate In N,N-dimethyl-formamide at 80℃;
8-<4-(4-pyrimidin-2-yl-piperazin-1-yl)but-2-enyl>-8-aza-spiro<4.5>decane-7,9-dione
118286-98-9

8-<4-(4-pyrimidin-2-yl-piperazin-1-yl)but-2-enyl>-8-aza-spiro<4.5>decane-7,9-dione

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate70%
8-(4-(piperazin-1-yl)butyl)-8-azaspiro[4.5]decane-7,9-dione
80827-59-4

8-(4-(piperazin-1-yl)butyl)-8-azaspiro[4.5]decane-7,9-dione

2-fluoropyrimidine
31575-35-6

2-fluoropyrimidine

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
With potassium hydroxide; hydroxypropyl methylcellulose In water at 20℃;62%
tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-(2-Pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane Bromide
81461-73-6

8-(2-Pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane Bromide

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
With potassium carbonate; 18-crown-6 ether In xylene for 6h; Heating;
With sodium hydroxide; potassium carbonate In N-methyl-acetamide; hydrogenchloride; water
8-<4-<4-(2-Pyrimidinyl)-1-piperazinyl>-2-butynyl>-8-azaspiro<4.5>decane-7,9-dione
118286-97-8

8-<4-<4-(2-Pyrimidinyl)-1-piperazinyl>-2-butynyl>-8-azaspiro<4.5>decane-7,9-dione

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In tetrahydrofuran for 0.833333h; Ambient temperature; Yield given;
N-(2-pyridinyl)piperazine
20980-22-7

N-(2-pyridinyl)piperazine

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 50 percent / Pd(PPh3)4 / tetrahydrofuran
2: 70 percent / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide
3: 70 percent / H2 / Pd/C / ethyl acetate
View Scheme
Multi-step reaction with 3 steps
1: 80 percent / Pd(PPh3)4 / tetrahydrofuran
2: 70 percent / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide
3: 70 percent / H2 / Pd/C / ethyl acetate
View Scheme
Multi-step reaction with 3 steps
1: 56 percent / Pd(PPh3)4 / tetrahydrofuran
2: 70 percent / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide
3: 70 percent / H2 / Pd/C / ethyl acetate
View Scheme
tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide
2: 70 percent / H2 / Pd/C / ethyl acetate
View Scheme
Multi-step reaction with 3 steps
1: 100 percent / K2CO3 / acetone / Heating
2: 65 percent / CuCl2 * 2 H2O / dioxane; H2O / 1.5 h / 70 - 80 °C
3: H2 / 10percent Pd/C / tetrahydrofuran / 0.83 h / Ambient temperature
View Scheme
4-(4-pyrimidin-2-yl-piperazin-1-yl)but-2-enyl acetate

4-(4-pyrimidin-2-yl-piperazin-1-yl)but-2-enyl acetate

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide
2: 70 percent / H2 / Pd/C / ethyl acetate
View Scheme
N-(2-pyridinyl)piperazine
20980-22-7

N-(2-pyridinyl)piperazine

methyl halide

methyl halide

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / CuCl2 * 2 H2O / dioxane; H2O / 1.5 h / 70 - 80 °C
2: H2 / 10percent Pd/C / tetrahydrofuran / 0.83 h / Ambient temperature
View Scheme
3,3-tetramethylene glutaric anhydride
5662-95-3

3,3-tetramethylene glutaric anhydride

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / 7percent aq. NH3 / tetrahydrofuran / 190 °C
2: 100 percent / K2CO3 / acetone / Heating
3: 65 percent / CuCl2 * 2 H2O / dioxane; H2O / 1.5 h / 70 - 80 °C
4: H2 / 10percent Pd/C / tetrahydrofuran / 0.83 h / Ambient temperature
View Scheme
8-Propargyl-8-azaspiro<4.5>decane-7,9-dione
25032-23-9

8-Propargyl-8-azaspiro<4.5>decane-7,9-dione

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / CuCl2 * 2 H2O / dioxane; H2O / 1.5 h / 70 - 80 °C
2: H2 / 10percent Pd/C / tetrahydrofuran / 0.83 h / Ambient temperature
View Scheme
BUSPIRONE
36505-84-7

BUSPIRONE

C21H29(2)H2N5O2

C21H29(2)H2N5O2

Conditions
ConditionsYield
With [(N,N′-bis(2,6-diisopropylphenyl)-2,3-butanediimine)Ni(μ−H)]2; deuterium In tetrahydrofuran at -196 - 45℃; under 760.051 Torr; for 24h; Reagent/catalyst; Sealed tube;98%
BUSPIRONE
36505-84-7

BUSPIRONE

C21H21(2)H10N5O2*ClH

C21H21(2)H10N5O2*ClH

Conditions
ConditionsYield
Stage #1: BUSPIRONE With water-d2; lithium carbonate; triisopropylsilanethiol In 1-methyl-pyrrolidin-2-one at 20℃; Irradiation;
Stage #2: With hydrogenchloride In 1-methyl-pyrrolidin-2-one		88%
BUSPIRONE
36505-84-7

BUSPIRONE

A

6'-Hydroxybuspirone
125481-61-0

6'-Hydroxybuspirone

B

6,10-dihydroxybuspirone

6,10-dihydroxybuspirone

Conditions
ConditionsYield
With sodium hexamethyldisilazane; triethyl phosphite In tetrahydrofuran at -60 - 20℃; Large scale;A 71%
B 13 %Chromat.
triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
745783-97-5

triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

BUSPIRONE
36505-84-7

BUSPIRONE

8-(4-(4-(4-(triethylsilyl)pyrimidin-2-yl)piperazin-1-yl)butyl)-8-azaspiro[4.5]decane-7,9-dione

8-(4-(4-(4-(triethylsilyl)pyrimidin-2-yl)piperazin-1-yl)butyl)-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
With 1,2-dimethoxyethane; potassium hexamethylsilazane for 3h; Inert atmosphere; regioselective reaction;29%
sodium 7‐azido‐1,1‐difluoroheptane‐1‐sulfinate

sodium 7‐azido‐1,1‐difluoroheptane‐1‐sulfinate

BUSPIRONE
36505-84-7

BUSPIRONE

C28H42F2N8O2
1450912-68-1

C28H42F2N8O2

Conditions
ConditionsYield
With tert.-butylhydroperoxide; toluene-4-sulfonic acid; zinc(II) chloride In water; dimethyl sulfoxide at 50℃; Cooling with ice;9%
2-oxo-2-(4-(prop-2-yn-1-yloxy)phenyl)acetic acid

2-oxo-2-(4-(prop-2-yn-1-yloxy)phenyl)acetic acid

BUSPIRONE
36505-84-7

BUSPIRONE

C31H37N5O4

C31H37N5O4

Conditions
ConditionsYield
With ammonium peroxydisulfate; silver nitrate; trifluoroacetic acid In dichloromethane; water at 60℃; for 3h;9%
BUSPIRONE
36505-84-7

BUSPIRONE

5-Hydroxybuspirone

5-Hydroxybuspirone

Conditions
ConditionsYield
Stage #1: BUSPIRONE With ethylenediaminetetraacetic acid trisodium salt; oxygen; manganese (II) acetate tetrahydrate; ascorbic acid In water pH=4; Udenfriend reaction;
Stage #2: With ferrous(II) sulfate heptahydrate; ethylenediaminetetraacetic acid trisodium salt; oxygen In water at 45℃; for 2h; Udenfriend reaction;		5.16%
BUSPIRONE
36505-84-7

BUSPIRONE

Buspirone N-oxide

Buspirone N-oxide

Conditions
ConditionsYield
With Davis' N-sulfonyloxaziridine In dichloromethane at 25℃; for 1h; Yield given;
BUSPIRONE
36505-84-7

BUSPIRONE

(R)-6'-Hydroxybuspirone

(R)-6'-Hydroxybuspirone

Conditions
ConditionsYield
With Bacillus megaterium cytochrome P450 9-10A-F87A monooxygenase; NADPH In various solvents at 20℃; for 3h; pH=8.2;
BUSPIRONE
36505-84-7

BUSPIRONE

6'-Hydroxybuspirone
125481-61-0

6'-Hydroxybuspirone

Conditions
ConditionsYield
Stage #1: BUSPIRONE With sodium hexamethyldisilazane; triethyl phosphite In tetrahydrofuran at -70 - -10℃; Large scale;
Stage #2: With oxygen In tetrahydrofuran at -37℃; Large scale;
Stage #1: BUSPIRONE With sodium hexamethyldisilazane; triethyl phosphite In tetrahydrofuran at -38 - -33℃;
Stage #2: With oxygen In tetrahydrofuran at -40 - -28℃;
BUSPIRONE
36505-84-7

BUSPIRONE

C21H30N5O2(1-)*K(1+)

C21H30N5O2(1-)*K(1+)

Conditions
ConditionsYield
With potassium hexamethylsilazane In tetrahydrofuran
BUSPIRONE
36505-84-7

BUSPIRONE

C21H31N5O4

C21H31N5O4

Conditions
ConditionsYield
Stage #1: BUSPIRONE In tetrahydrofuran Alkaline conditions;
Stage #2: With oxygen
BUSPIRONE
36505-84-7

BUSPIRONE

C21H21(3)H10N5O2

C21H21(3)H10N5O2

Conditions
ConditionsYield
With tritium oxide In 1-methyl-pyrrolidin-2-one at 20℃; Irradiation;

Buspirone Specification

The Buspirone with the cas number 21535-47-7, is also called (1)8-(4-(4-(2-Pyrimidinyl)-1-piperizinyl)butyl)-8-azaspiro(4,5)decane-7,9-dione; (2) Ansial ; (3) Buspirona ; (4) Buspirone ; (5) Buspironum ; (6)8-Azaspiro(4,5)decane-7,9-dione, 8-(4-(4-(2-pyrimidinyl)piperizinyl)butyl)-; (7)8-Azaspiro(4.5)decane-7,9-dione, 8-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-. It belongs to Serotonin receptor product categories. 

Properties of Bolvidon are: (1)ACD/LogP: 3.43 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 2.26 ; (4)ACD/LogD (pH 7.4): 3.37 ; (5)ACD/BCF (pH 5.5): 16.18 ; (6)ACD/BCF (pH 7.4): 205.29 ; (7)ACD/KOC (pH 5.5): 118.63 ; (8)ACD/KOC (pH 7.4): 1504.97 ; (9)#H bond acceptors: 7 ; (10)#H bond donors: 0 ; (11)#Freely Rotating Bonds: 6 ; (12)Polar Surface Area: 69.64 Å2 ; (13)Index of Refraction: 1.603 ; (14) Molar Refractivity: 106.83 cm3 ; (15)Molar Volume: 310.6 cm3 ; (16)Polarizability: 42.35 ×10-24 cm3 ; (17)Surface Tension: 62.3 dyne/cm ; (18)Density: 1.24 g/cm3 ; (19)Flash Point: 325.1 °C ; (20)Enthalpy of Vaporization: 91.11 kJ/mol ; (21)Boiling Point: 613.9 °C at 760 mmHg ; (22)Vapour Pressure: 5.24E-15 mmHg at 25°C

The Buspirone shows no potential for addiction or dependence, and the development of tolerance has not been observed. The main disadvantage of Buspirone (CAS NO.36505-84-7) is that it may take several weeks before its anxiolytic effects become noticeable. Often patients have to be initially co-treated with a benzodiazepine for an immediate anxiolytic effect. It functions as a serotonin 5-HT1A receptor partial agonist. Side effects have been reported, but are not more frequent than those encountered with placebo.

The Buspirone can be obtained by reaction of 2-piperazino-pyrimidine with 8-aza-spiro[4.5]decane-7,9-dione and 1,4-dibromo-butane. This reaction progress with triethylbenzylammonium bromide as catalytic agent, reflux in xylene for 3 h, or reflux for 5 h. This reaction can also goes with other imides and catalysts, variation of reaction time, also in toluene and also 1-(2-quinolinyl)piperazine.
 
 ++

 

You can still convert the following datas into molecular structure :
1. SMILES: O=C1N(C(=O)CC2(C1)CCCC2)CCCCN4CCN(c3ncccn3)CC4
2. 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

The Buspirone toxic data can be showed in the following sheet.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo unreported 399mg/kg/19D- (399mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Drugs of the Future. Vol. 1, Pg. 409, 1976.

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