Noscapine
Title: Noscapine
CAS Registry Number: 128-62-1
CAS Name: (3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone
Additional Names: narcotine; l-a-narcotine; l-a-2-methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxy-3-phthalidyl)-1,2,3,4-tetrahydroisoquinoline; narcosine; methoxyhydrastine; opian; opianine
Manufacturers' Codes: NSC-5366
Trademarks: Nipaxon (Pharmacia)
Molecular Formula: C22H23NO7
Molecular Weight: 413.42
Percent Composition: C 63.91%, H 5.61%, N 3.39%, O 27.09%
Literature References: An opium alkaloid, isolated from the plant Papaver somniferum L. Papaveraceae. Present in amounts up to 11% depending on season and locality. First isoln: Robiquet, Ann. Chim. Phys. [2] 5, 275 (1817). Extractable from the water-insoluble residue remaining from the processing of opium for the manufacture of morphine. Racemization to gnoscopine: Rabe, McMillian, Ann. 377, 233 (1910); and structural studies: Perkin, Robinson, J. Chem. Soc. 99, 775 (1911); Marshall et al., ibid. 1934, 1318. Preliminary stereochemical studies: Ohta et al., Tetrahedron Lett. 1963, 1857; Battersby, Spenser, J. Chem. Soc. 1965, 1087. Revised stereochemistry: Blaha et al., Collect. Czech. Chem. Commun. 29, 2328 (1964); Snatzke et al., Tetrahedron 25, 5059 (1969). Synthesis of racemate: Kerekes, Bognar, J. Prakt. Chem. 313, 923 (1971). Biosynthesis: Battersby, Hirst, Tetrahedron Lett. 1965, 669. Metabolism: N. Tsunoda, Y. Yoshimura, Xenobiotica 9, 181 (1979); eidem, ibid. 11, 23 (1981). Pharmacokinetics: B. Dhalstroem et al., Eur. J. Clin. Pharmacol. 22, 535 (1982). Clinical evaluation as antitussive: D. W. Empey et al., ibid. 16, 393 (1979). HPLC determn in serum: K. M. Jensen, J. Chromatogr. 274, 381 (1983). Comprehensive description: M. A. Al-Yahya, M. M. A. Hassan, Anal. Profiles Drug Subs. 11, 407-461 (1982).
Properties: Orthorhombic bisphenoidal prisms, tablets from diacetone. Triboluminescent. d 1.395. mp 176°. Sublimes at 150-160° under 11 mm pressure at 2 mm distance. Very weak base forming unstable salts with acids and strong bases. pK 7.8. uv max (ethanol): 209, 291, 309-310 nm (log e 4.86, 3.60, 3.69). Practically insol in vegetable oils. Slightly sol in NH4OH, hot solns of KOH and NaOH, forming salts. Salts formed with acids are dextrorotatory and unstable in water.
Melting point: mp 176°
pKa: pK 7.8
Absorption maximum: uv max (ethanol): 209, 291, 309-310 nm (log e 4.86, 3.60, 3.69)
Density: d 1.395
 
Derivative Type: Hydrochloride
CAS Registry Number: 912-60-7
Trademarks: Capval (Dreluso)
Molecular Formula: C22H23NO7.HCl
Molecular Weight: 449.88
Percent Composition: C 58.73%, H 5.38%, N 3.11%, O 24.89%, Cl 7.88%
Properties: Hemihydrate to tetrahydrate, crystals, very sol in water forming basic salts.
 
Derivative Type: Camphorsulfonate
CAS Registry Number: 25333-79-3
Trademarks: Tulisan (Chiesi)
Molecular Formula: C22H23NO7.C10H16O4S
Molecular Weight: 645.72
Percent Composition: C 59.52%, H 6.09%, N 2.17%, O 27.26%, S 4.97%
Properties: Contains 35.97% camphosulfonic acid. Prepn: Maillard, US 3108106 (1963 to Jacques Logeais). Crystals, mp 188-191°. [a]D33 +32.7° (c = 4.56 in water). Freely sol in water. Sol in methanol, ethanol. Slightly sol in ethyl acetate. Practically insol in ether.
Melting point: mp 188-191°
Optical Rotation: [a]D33 +32.7° (c = 4.56 in water)
 
Derivative Type: dl-Form
CAS Registry Number: 6035-40-1
Additional Names: dl-Narcotine; gnoscopine
Properties: Long needles from methanol, mp 232° (dec). pK 7.8. Freely sol in carbon disulfide, hot chloroform; sol in ~1500 parts alcohol; sparingly sol in benzene, water.
Melting point: mp 232° (dec)
pKa: pK 7.8
 
Therap-Cat: Antitussive.
Keywords: Antitussive.

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