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Pilocarpine

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Name

Pilocarpine

EINECS 202-128-4
CAS No. 92-13-7 Density 1.22 g/cm3
PSA 44.12000 LogP 1.16180
Solubility N/A Melting Point 34°
Formula C11H16N2O2 Boiling Point 431.8 °C at 760 mmHg
Molecular Weight 208.26 Flash Point 215 °C
Transport Information N/A Appearance N/A
Safety 25-45 Risk Codes 26/28
Molecular Structure Molecular Structure of 92-13-7 (PILOCARPINE) Hazard Symbols VeryT+
Synonyms

2(3H)-Furanone,3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, (3S-cis)-;Pilocarpine(8CI);(+)-Pilocarpine;Ocucarpine;Ocusert P 20;Ocusert Pilo;Ocusert Pilo40;Pilocarpine, (+)-;Pilocarpol;Pilokarpin;Syncarpine;

Article Data 31

Pilocarpine Consensus Reports

Reported in EPA TSCA Inventory.

Pilocarpine Specification

The Pilocarpine, with the CAS registry number 92-13-7, is also known as (3S-cis)-3-Ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone. Its EINECS registry number is 202-128-4. This chemical's molecular formula is C11H16N2O2 and molecular weight is 208.26. Its IUPAC name is called (3S,4R)- 3-ethyl- 4-((1-methyl- 1H-imidazol- 5-yl) methyl)dihydrofuran- 2(3H)-one.

Physical properties of Pilocarpine: (1)ACD/LogP: -0.10; (2)ACD/LogD (pH 5.5): -1.58; (3)ACD/LogD (pH 7.4): -0.24; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 14.99; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.584; (11)Molar Refractivity: 57.02 cm3; (12)Molar Volume: 170.1 cm3; (13)Surface Tension: 41.9 dyne/cm; (14)Density: 1.22 g/cm3; (15)Flash Point: 215 °C; (16)Enthalpy of Vaporization: 68.75 kJ/mol; (17)Boiling Point: 431.8 °C at 760 mmHg; (18)Vapour Pressure: 1.16E-07 mmHg at 25°C.

Preparation of Pilocarpine: The drug and powdered leaf of pilocarpin microfelixis are subjected to extracted forotoal alkaloid with ethanol acidified with HCL with solvents removed under reduced pressure and resultant aqueous residue is neutralized with ammonia and kept aside till all the resin is settled down completely. It is filtered and concentrated by sugar solution to a small volume, made alkaloid with ammonia, and finally extracted with chloroform. The solvent is removed under reduced pressure.

Uses: Pilocarpine has been used in the treatment of chronic open-angle glaucoma and acute angle-closure glaucoma for over 100 years. Pilocarpine is often used as an antidote for scopolamine, atropine, and hyoscyamine poisoning. In ophthalmology pilocarpine is also used to reduce the possibility of glare at night from lights if the patient underwent implantation of phakic intraocular lenses; the use of pilocarpine would reduce the size of the pupils, relieving these symptoms. The most common concentration for this use is pilocarpine 1%, the weakest concentration.Pilocarpine is also used to treat dry mouth (xerostomia) which can occur, for example, as a side effect of radiation therapy for head and neck cancers. Pilocarpine stimulates the secretion of large amounts of saliva and sweat. Pilocarpine is used to stimulate sweat glands in a sweat test to measure the concentration of chloride and sodium that is excreted in sweat. It is used to diagnose cystic fibrosis (CF).

When you are using this chemical, please be cautious about it as the following:
This chemical that at very low levels may cause damage to health. It is very toxic by inhalation and if swallowed. You must avoid contact with eyes. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCC1C(COC1=O)CC2=CN=CN2C
(2)Isomeric SMILES: CC[C@H]1[C@H](COC1=O)CC2=CN=CN2C
(3)InChI: InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8-,10-/m0/s1
(4)InChIKey: QCHFTSOMWOSFHM-WPRPVWTQSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human LDLo subcutaneous 143ug/kg (0.143mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Confinia Neurologica. Vol. 10, Pg. 8, 1949.
man LDLo unreported 1912ug/kg (1.912mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 220mg/kg (220mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 192, Pg. 88, 1971.
mouse LD50 intravenous 61900ug/kg (61.9mg/kg)   Drugs in Japan Vol. 6, Pg. APP-16, 1982.
mouse LD50 oral 119mg/kg (119mg/kg)   Drugs in Japan Vol. 6, Pg. APP-16, 1982.
mouse LD50 subcutaneous 90900ug/kg (90.9mg/kg)   Drugs in Japan Vol. 6, Pg. APP-16, 1982.
rabbit LDLo intravenous 120mg/kg (120mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1386, 1935.
rat LD50 intraperitoneal 166mg/kg (166mg/kg)   Drugs in Japan Vol. 6, Pg. APP-16, 1982.
rat LD50 intravenous 88500ug/kg (88.5mg/kg)   Drugs in Japan Vol. 6, Pg. APP-16, 1982.
rat LD50 oral 402mg/kg (402mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 1204, 1981.
rat LD50 subcutaneous 366mg/kg (366mg/kg)   Drugs in Japan Vol. 6, Pg. APP-16, 1982.
women TDLo subcutaneous 1143ug/kg (1.143mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
Archives of Ophthalmology Vol. 105, Pg

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