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CAS No 92-13-7 , (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one

  • Name: (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one
  • Synonyms: Ocusert pilo;(3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one; Salagen;Isoptocarpine; Syncarpine; Pilokarpol; Ocusert pilo-20; Pilocarpol; Pilokarpin; Pilocarpin;
  • CAS Registry Number:
  • Transport: 1544
  • Boiling Point: 260 DEG C @ 5 MM HG (PARTIAL CONVERSION TO ISOPILOCARPINE)
  • Density: 1.22 g/cm3
  • Safety Statements: A human poison by subcutaneous route. Poison experimentally by ingestion, intravenous, intraperitoneal, and subcutaneous routes. A very poisonous alkaloid that is used to remove excess fluid accumulations from the body. Its action on the sweat glands makes it a powerful sudorific. It very rarely causes death, but, when it does, it is by paralysis of the heart or edema of the lungs. Dangerous; on heating to decomposition it emits toxic fumes of NOx.
  • Hazard Symbols: T+: Very toxic;
  • EINECS: 202-128-4
  • Molecular Weight: 208.25694
  • InchiKey: QCHFTSOMWOSFHM-WPRPVWTQSA-N
  • 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
  • Risk Statements: 26/28
  • Molecular Formula: C11H16N2O2
  • Molecular Structure:CAS No:92-13-7 (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one

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92-13-7 PILOCARPINE

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92-13-7 pilocarpine

  • IUPAC NAME-(3S,4R)-3-Ethyl-4-((1-methyl-1H-imidazol-5-yl)methyl)dihydrofuran-2(3H)-one MOLECULAR FORMULA-C11H16N2O2 MOLAR MASS-208.257 g/mol Pilocarpine is a parasympathomimetic alkaloid obtained from the leaves of tropical American shrubs from the g...
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92-13-7 Pilocarpine

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92-13-7 PILOCARPINE(RG)

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92-13-7 (+)-PILOCARPINE-D5 HYDROCHLORIDE

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References of (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one
Title: Pilocarpine
CAS Registry Number: 92-13-7
CAS Name: (3S-cis)-3-Ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone
Trademarks: Ocusert Pilo (Cusi)
Molecular Formula: C11H16N2O2
Molecular Weight: 208.26
Percent Composition: C 63.44%, H 7.74%, N 13.45%, O 15.36%
Literature References: Cholinergic principle from Pilocarpus jaborandi Holmes, Rutaceae. Isoln: Petit, Polanovski, Bull. Soc. Chim. [3] 17, 557, 702 (1897). Structure: Jowett, J. Chem. Soc. 77, 473, 851 (1900); 83, 438 (1903). Stereoisomeric with isopilocarpine: Polonovski, Polonovski, Bull. Soc. Chim. [4] 31, 1314 (1922). Has the cis configuration; isopilocarpine is trans: Zav'yalov, Dokl. Akad. Nauk SSSR 82, 257 (1952). Absolute configuration: Hill, Barcza, Tetrahedron 22, 2889 (1966). Synthesis: Preobrashenski et al., Ber. 66, 1187 (1933); Samokhvalov, Med. Prom. SSSR 11, no. 2, 10 (1957); DeGraw, Tetrahedron 28, 967 (1972); Link, Bernauer, Helv. Chim. Acta 55, 1053 (1972). Stereoselective synthesis: A. Noordam et al., Rec. Trav. Chim. 98, 467 (1979). Review: Langenbeck, Angew. Chem. 60, 297 (1948); van Rossum et al., Experientia 16, 373 (1960). Toxicity studies: Beccari, Boll. Chim. Farm. 106, 8 (1967). Comprehensive description: A. A. Al-Badr, H. Y. Aboul-Enein, Anal. Profiles Drug Subs. 12, 385-432 (1983). Clinical trial in Sj?gren's syndrome: F. B. Vivino et al., Arch. Intern. Med. 159, 174 (1999); in radiation-induced xerostomia: J.-C. Horiot et al., Radiother. Oncol. 55, 233 (2000).
Properties: Oil or crystals, mp 34°. bp5 260° (partial conversion to isopilocarpine). [a]D18 +106° (c = 2). pK1 (20°) 7.15; pK2 (20°) 12.57. Sol in water, alcohol, chloroform; sparingly sol in ether, benzene. Almost insol in petr ether.
Melting point: mp 34°
Boiling point: bp5 260° (partial conversion to isopilocarpine)
pKa: pK1 (20°) 7.15; pK2 (20°) 12.57
Optical Rotation: [a]D18 +106° (c = 2)
 
Derivative Type: Hydrochloride
CAS Registry Number: 54-71-7
Trademarks: Akarpine (Akorn); Almocarpine (Ayerst); Isopto Carpine (Alcon); Pilogel (Alcon); Pilopine HS (Alcon); Pilostat (Bausch & Lomb); Salagen (MGI)
Molecular Formula: C11H16N2O2.HCl
Molecular Weight: 244.72
Percent Composition: C 53.99%, H 7.00%, N 11.45%, O 13.08%, Cl 14.49%
Properties: Hygroscopic crystals from alcohol, mp 204-205°. [a]D18 +91° (c = 2). Freely sol in water, alcohol. Practically insol in ether, chloroform. Keep well closed and protected from light.
Melting point: mp 204-205°
Optical Rotation: [a]D18 +91° (c = 2)
 
Derivative Type: Nitrate
CAS Registry Number: 148-72-1
Trademarks: Chibro Pilocarpine (Chibret); Licarpin (Allergan); Pilo (Novopharma); Pilofrin (Allergan); Pilagan (Allergan)
Molecular Formula: C11H16N2O2.HNO3
Molecular Weight: 271.27
Percent Composition: C 48.70%, H 6.32%, N 15.49%, O 29.49%
Properties: mp 173.5-174.0° (dec). Poisonous! [a]D +77 to +83° (c = 10). One gram dissolves in 4 ml water, 75 ml alcohol. Insol in chloroform, ether. Incompat. Silver nitrate, mercury bichloride, iodides, gold salts, tannin, calomel, KMnO4, alkalies.
Melting point: mp 173.5-174.0° (dec)
Optical Rotation: [a]D +77 to +83° (c = 10)
 
Derivative Type: Isopilocarpine
Synonyms: b-Pilocarpine
Properties: Hygroscopic oily liquid or prisms. bp10 261°. [a]D18 +50° (c = 2). pK1 (18°) 7.17. Miscible with water and alcohol; very sol in chloroform; less sol in benzene, ether. Almost insol in petr ether.
Boiling point: bp10 261°
pKa: pK1 (18°) 7.17
Optical Rotation: [a]D18 +50° (c = 2)
 
Derivative Type: Isopilocarpine hydrochloride hemihydrate
Molecular Formula: C11H16N2O2.HCl.?H2O
Molecular Weight: 253.73
Percent Composition: C 52.07%, H 7.15%, N 11.04%, O 15.76%, Cl 13.97%
Properties: Scales from alcohol + ether, mp 127°; when anhydr, mp 161°. [a]D18 +39° (c = 5). Sol in 0.27 part water; 2.1 parts alcohol.
Melting point: mp 127°; mp 161°
Optical Rotation: [a]D18 +39° (c = 5)
 
Derivative Type: Isopilocarpine nitrate
Molecular Formula: C11H16N2O2.HNO3
Molecular Weight: 271.27
Percent Composition: C 48.70%, H 6.32%, N 15.49%, O 29.49%
Properties: Prisms from water, scales from alcohol, mp 159°. [a]D18 +39° (c = 2). Sol in 8.4 parts water, in 350 parts abs alcohol.
Melting point: mp 159°
Optical Rotation: [a]D18 +39° (c = 2)
 
Therap-Cat: Antiglaucoma agent; miotic; sialogogue.
Therap-Cat-Vet: Parasympathomimetic; miotic; gastric secretory stimulant.
Keywords: Antiglaucoma; Miotic; Sialagogue.