Scopolamine
Title: Scopolamine
CAS Registry Number: 51-34-3
CAS Name: (aS)-a-(Hydroxymethyl)benzeneacetic acid (1a,2b,4b,5a,7b)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester
Additional Names: 6b,7b-epoxy-1aH,5aH-tropan-3a-ol (-)-tropate; 6b,7b-epoxy-3a-tropanyl S-(-)-tropate; 6,7-epoxytropine tropate; scopine tropate; tropic acid ester with scopine; hyoscine; l-scopolamine
Trademarks: Scopoderm TTS (Novartis); Transcop (Recordati); Transderm Scop (Novartis)
Molecular Formula: C17H21NO4
Molecular Weight: 303.35
Percent Composition: C 67.31%, H 6.98%, N 4.62%, O 21.10%
Literature References: Anticholinergic, tropane alkaloid isolated from Datura metel L., Scopola carniolica Jacq. and other Solanaceae. Constituent of impure duboisine from Duboisia myoporoides R. Br., pure duboisine is l-hyoscyamine, q.v. Isoln: A. Ladenburg, Ann. 206, 274 (1881); E. Schmidt, Arch. Pharm. 230, 207 (1892). Identity with hyoscine: O. Hesse, Ann. 271, 100 (1892); idem, J. Prakt. Chem. 66, 194 (1902). Absorption spectra: J. J. Dobbie, J. J. Fox, J. Chem. Soc. 103, 1194 (1913). Resolution of isomers and review of early literature: H. King, ibid. 1919, 476. Extraction procedure: F. Chemnitius, J. Prakt. Chem. 120, 221 (1928). Structural studies: J. Gadamer, F. Hammer, Arch. Pharm. 259, 122 (1921); K. Hess, O. Wahl, Ber. 55, 1979 (1922); R. Willstätter, E. Berner, ibid. 56, 1079 (1923); W. Steffens, Arch. Pharm. 262, 205 (1924). Configuration: G. Fodor, Nature 170, 278 (1952); J. Meinwald, J. Chem. Soc. 1953, 712. Review of stereochemistry: G. Fodor, Tetrahedron 1, 86 (1957). Absolute configuration of tropic acid moiety: G. Fodor, G. Csepreghy, Tetrahedron Lett. 1959, 16; eidem, J. Chem. Soc. 1961, 3222. Synthesis of DL-form: G. Fodor et al., Chem. Ind. (London) 1956, 764; P. Dobo et al., J. Chem. Soc. 1959, 3461. Clinical evaluation in motion sickness: J. J. Brand, P. Whittingham, Lancet 2, 232 (1970); in peripheral vertigo: T. Rahko, P. Karma, J. Laryngol. Otol. 99, 653 (1985). Acute toxicity of the hydrobromide: Stockhaus, Wick, Arch. Int. Pharmacodyn. Ther. 180, 155 (1969). Review of CNS effects in humans: D. J. Safer, R. P. Allen, Biol. Psychiatry 3, 347-355 (1971); of use in anesthesia: L. E. Shutt, J. B. Bowles, Anaesthesia 34, 476-490 (1979); of pharmacology and clinical efficacy: S. P. Clissold, R. C. Heel, Drugs 29, 189-207 (1985). Comprehensive description: F. J. Muhtadi, M. M. A. Hassan, Anal. Profiles Drug Subs. 19, 477-551 (1990).
Properties: Viscous liquid. pKa 7.55-7.81. [a]D20 -28° (c = 2.7). Sol in 9.5 parts water at 15°. Forms a cryst monohydrate, mp 59°. Freely sol in hot water, in alcohol, ether, chloroform, acetone. Sparingly sol in benzene, petr ether. Easily hydrolyzed by acids or alkalies. Dec on standing.
Melting point: mp 59°
pKa: pKa 7.55-7.81
Optical Rotation: [a]D20 -28° (c = 2.7)
 
Derivative Type: Hydrobromide trihydrate
CAS Registry Number: 114-49-8
Additional Names: Scopolammonium bromide
Molecular Formula: C17H21NO4.HBr.3H2O
Molecular Weight: 438.31
Percent Composition: C 46.58%, H 6.44%, N 3.20%, O 25.55%, Br 18.23%
Properties: Orthorhombic sphenoidal crystals from water, slightly efflorescent in dry air. mp 195° (after drying at 105° for 3 hours). [a]D25 -24 to -26° (c = 5, calculated on anhydrous basis). uv max (methanol) 246, 252, 258, 264 nm (A1%1cm 3.5, 4.0, 4.5, 3.0). pH of 0.05M soln 5.85. One gram dissolves in 1.5 ml water, 20 ml alcohol. Slightly sol in chloroform. Practically insol in ether. LD50 in rats (mg/kg): 3800 s.c. (Stockhaus, Wick).
Melting point: mp 195° (after drying at 105° for 3 hours)
Optical Rotation: [a]D25 -24 to -26° (c = 5, calculated on anhydrous basis)
Absorption maximum: uv max (methanol) 246, 252, 258, 264 nm (A1%1cm 3.5, 4.0, 4.5, 3.0)
Toxicity data: LD50 in rats (mg/kg): 3800 s.c. (Stockhaus, Wick)
 
Derivative Type: Hydrochloride
CAS Registry Number: 55-16-3
Molecular Formula: C17H21NO4.HCl
Molecular Weight: 339.81
Percent Composition: C 60.09%, H 6.53%, N 4.12%, O 18.83%, Cl 10.43%
Properties: Crystals from acetone, mp 200°. Dihydrate, prisms from water, melts in water of crystn at 80°. Very sol in water and alcohol. pH of 0.05M soln 5.85.
Melting point: mp 200°
 
Derivative Type: Methyl bromide see Methscopolamine Bromide
 
Derivative Type: Methyl nitrate
CAS Registry Number: 6106-46-3
Additional Names: Methscopolamine nitrate
Molecular Formula: C17H21NO4.CH3NO3
Molecular Weight: 380.39
Percent Composition: C 56.83%, H 6.36%, N 7.36%, O 29.44%
Properties: Crystals. Freely sol in water, dil alcohol; slightly sol in abs alcohol.
 
Derivative Type: DL-Form
Additional Names: Atroscine
Properties: Dihydrate, chisel-shaped prisms from ethanol + water, mp 38-40°. Monohydrate, efflorescent crystals, mp 55-57°. Anhydrous, long prisms, mp 82-83°. Very slightly sol in water; sol in alc, chloroform, ether, oils.
Melting point: mp 38-40°; mp 55-57°; mp 82-83°
 
Therap-Cat: In treatment of motion sickness; antiemetic; antispasmodic; mydriatic; preanesthetic medicant.
Therap-Cat-Vet: Preanesthetic medicant.
Keywords: Antiemetic; Mydriatic; Antispasmodic; Antimuscarinic.

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