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Benztropine mesylate

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Name

Benztropine mesylate

EINECS 205-048-8
CAS No. 132-17-2 Density N/A
PSA 75.22000 LogP 4.94050
Solubility Soluble in water (81 mg/ml at 25°C), DMSO (50 mg/ml at 25°C), ethanol (81 mg/ml at 25°C), and ether (very slightly). Melting Point 135 °C(lit.)
Formula C21H25NO.CH4O3S Boiling Point 547.8 °C at 760 mmHg
Molecular Weight 403.543 Flash Point 285.1 °C
Transport Information UN 2811 6.1/PG 3 Appearance White to off-white solid
Safety 36/37/39-45 Risk Codes 23/24/25
Molecular Structure Molecular Structure of 132-17-2 (Benztropine mesylate) Hazard Symbols ToxicT
Synonyms

Cobrentin methanesulfonate;endo-3-(Diphenylmethoxy)-8-methyl-8-azoniabicyclo(3.2.1)octane methanesulphonate;(1R)-3-benzhydryloxy-8-methyl-8-azabicyclo[3.2.1]octane; methanesulfonic acid;8-Azabicyclo[3.2.1]octane, 3- (diphenylmethoxy)-8-methyl-, endo-, methanesulfonate;Cogentin methanesulfonate;Benzotropine methanesulfonate;(1R,5R)-3-benzhydryloxy-8-methyl-8-azabicyclo[3.2.1]octane; methanesulfonic acid;Benztropine mesylate (USP);1-alpha-H,5-alpha-H-Tropane, 3-alpha-(diphenylmethoxy)-, methanesulfonate;8-Azabicyclo(3.2.1)octane, 3-(diphenylmethoxy)-, endo-, methanesulfonate;Benztropine methanesulfonate;Benzotropinemesylate;8-Azabicyclo(3.2.1)octane, 3-(diphenylmethoxy)-8-methyl-, endo-, methanesulfonate (9CI);Benztropine mesilate (JAN);Cogentin Mesylate;8-Azabicyclo[3.2.1]octane,3-(diphenylmethoxy)- 8-methyl-,(3-endo)-,methanesulfonate;3-benzhydryloxy-8-methyl-8-azabicyclo[3.2.1]octane; methanesulfonic acid;Cogentin (TN);Benzatropine methanesulfonate;3-Diphenyl methoxytropane methanesulfonate;Benztropine mesilate;1alphaH,5alphaH-Tropane, 3alpha-(diphenylmethoxy)-, methanesulfonate (8CI);Tropine benzohydryl ether methanesulfonate;

 

Benztropine mesylate Synthetic route

132-17-2

benztropine mesylate

17341-93-4

2,2,2-Trichloroethyl chloroformate

2,2,2-Trichlorocarboethoxydesmethylbenztropine

Conditions
ConditionsYield
With potassium carbonate In benzene for 60h; Substitution; Heating;80%
132-17-2

benztropine mesylate

3α-benzhydryloxy-8-azabicyclo[3.2.1]octane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / K2CO3 / benzene / 60 h / Heating
2: 50 percent / Zn / methanol / 2 h / Heating
View Scheme

Benztropine mesylate Chemical Properties

CAS: 132-17-2
EINECS: 205-048-8
Product Categories: Intermediates & Fine Chemicals ; Pharmaceuticals .
Following is the Molecular Structure of Tropine benzohydryl ether methane-sulfonate (132-17-2):

SMILES: CN4[C@@H]1CC[C@H]4C[C@H](C1)OC(c2ccccc2)c3ccccc3.CS(O)(=O)=O
InChI: InChI=1/C21H25NO.CH4O3S/c1-22-18-12-13-19(22)15-20(14-18)23-21(16-8-4-2-5-9-16)17-10-6-3-7-11-17;1-5(2,3)4/h2-11,18-21H,12-15H2,1H3;1H3,(H,2,3,4)/t18-,19+,20+;
InChIKey: CPFJLLXFNPCTDW-BWSPSPBFBO
Std.InChI: InChI=1S/C21H25NO.CH4O3S/c1-22-18-12-13-19(22)15-20(14-18)23-21(16-8-4-2-5-9-16)17-10-6-3-7-11-17;1-5(2,3)4/h2-11,18-21H,12-15H2,1H3;1H3,(H,2,3,4)/t18-,19+,20+;
Std.InChIKey: CPFJLLXFNPCTDW-BWSPSPBFSA-N
Molecular Formula: C22H29NO4S
Molecular Weight: 403.53
Melting Point: 135℃(lit.)
Boiling Point: 547.8℃ at 760mmHg
Flash Point: 285.1℃
Enthalpy of Vaporization: 87.05kJ/mol
Vapour Pressure: 7.83E-13mmHg at 25℃

Benztropine mesylate Uses

 Tropine benzohydryl ether methane-sulfonate (132-17-2) can be used as an antiparkinsonian.

Benztropine mesylate Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 33mg/kg (33mg/kg)   Compilation of LD50 Values of New Drugs.
guinea pig LD50 subcutaneous 80mg/kg (80mg/kg) AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC Archives Internationales de Pharmacodynamie et de Therapie. Vol. 137, Pg. 375, 1962.
human TDLo oral 100ug/kg (0.1mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS Proceedings of the European Society for the Study of Drug Toxicity. Vol. 8, Pg. 59, 1967.
mouse LD50 intraperitoneal 65mg/kg (65mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 144, Pg. 555, 1963.
mouse LD50 intravenous 24mg/kg (24mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 208, 1972.
mouse LD50 oral 91mg/kg (91mg/kg)   Drugs in Japan Vol. 6, Pg. 775, 1982.
mouse LD50 subcutaneous 103mg/kg (103mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 208, 1972.
rat LD50 oral 940mg/kg (940mg/kg)   Drugs in Japan Vol. 6, Pg. 775, 1982.
rat LD50 subcutaneous 353mg/kg (353mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 208, 1972.

Benztropine mesylate Safety Profile

Hazard Codes:  T Toxic.
Risk Statements: 23/24/25
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 36/37/39-45
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).
RIDADR: UN 2811 6.1/PG 3
WGK: Germany 3
RTECS: YM3150000
Poison by ingestion, intravenous, subcutaneous, and intraperitoneal routes. Human systemic effects by ingestion: psychotropic effects. Mutation data reported.

Benztropine mesylate Specification

 Tropine benzohydryl ether methane-sulfonate (132-17-2) also can be called for Cogentin ; Cogentinol ; Benzotropine mesylate ; Benztropine mesylate ; Benztropine methanesulfonate ; 3-(Diphenylmethoxy)-8-methyl-8-azabicyclo[3.2.1]octane methane sulfonate ; 3-(Diphenylmethoxy)-8-azabicyclo(3.2.1)octanendo-8-azabicyclo(3.2.1)octanmethanesulfonate ; 3-alpha-(Diphenylmethoxy)-1-alpha-h,5-alpha-h-tropanemethanesulfonate . Tropine benzohydryl ether methane-sulfonate (132-17-2) is a white to off-white solid.When heated to decomposition it emits very toxic fumes of NOx and SOx .This chemical should be stored at 2-8℃.

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