Hyoscyamine
Title: Hyoscyamine
CAS Registry Number: 101-31-5
CAS Name: [3(S)-endo]-a-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
Additional Names: 1aH,5aH-tropan-3a-ol(-)-tropate (ester); 3a-tropanyl S-(-)-tropate; l-tropic acid ester with tropine; l-tropine tropate; daturine; duboisine; l-hyoscyamine
Trademarks: Cystospaz (Alcon); Levsin (Kremers-Urban)
Molecular Formula: C17H23NO3
Molecular Weight: 289.37
Percent Composition: C 70.56%, H 8.01%, N 4.84%, O 16.59%
Literature References: Anticholinergic. From Hyoscyamus niger L., Atropa belladonna L., Datura stramonium L., and other Solanaceae: Ladenburg, Ann. 206, 274 (1881). Identity with duboisine and daturine: Beckurts, Apoth. Ztg. 27, 683 (1912). Obtained by resolution of atropine: Werner, Miltenberger, Ann. 631, 163 (1960). Prepd from (-)-acetyltropoyl chloride and atropine hydrochloride: Fodor et al., Acta Chim. Acad. Sci. Hung. 28(4), 409 (1961), C.A. 61, 1903g (1964). Configuration: Fodor, Csepreghy, Tetrahedron Letters no. 7, 16 (1959). Comprehensive description: F. J. Muhtadi, Anal. Profiles Drug Subs. Excip. 23, 153-228 (1994).
Properties: Silky, tetragonal needles from evaporating alc. Keep well closed and protect from light and heat; easily racemized. mp 108.5°. [a]D20 -21.0° (alc). pKa (21°) 9.7. One gram dissolves in 281 ml water (pH 9.5), 69 ml ether, 150 ml benzene, 1 ml chloroform. Freely sol in alcohol, dil acids. uv max (methanol): 247, 252, 258, 264 nm (A1%1cm 5.18, 5.70, 6.12, 5.10). Absorption spectra: Dobbie, Fox, J. Chem. Soc. 103, 1194, 1195 (1913).
Melting point: mp 108.5°
pKa: pKa (21°) 9.7
Optical Rotation: [a]D20 -21.0° (alc)
Absorption maximum: uv max (methanol): 247, 252, 258, 264 nm (A1%1cm 5.18, 5.70, 6.12, 5.10)
 
Derivative Type: Hydrobromide
CAS Registry Number: 306-03-6
Molecular Formula: C17H23NO3.HBr
Molecular Weight: 370.28
Percent Composition: C 55.14%, H 6.53%, N 3.78%, O 12.96%, Br 21.58%
Properties: Deliquescent crystals, mp 152°. pH 5.4 (1 in 100). Levorotatory. Very sol in water. One gram dissolves in 3 ml alcohol, 1.2 ml chloroform, 2260 ml ether.
Melting point: mp 152°
 
Derivative Type: Hydrochloride
Molecular Formula: C17H23NO3.HCl
Molecular Weight: 325.83
Percent Composition: C 62.67%, H 7.42%, N 4.30%, O 14.73%, Cl 10.88%
Properties: Crystals. Poisonous! mp 149-151°. Freely sol in water, alcohol.
Melting point: mp 149-151°
 
Derivative Type: Methyl bromide
Additional Names: N-Methylhyoscyaminium bromide
Molecular Formula: C17H23NO3.CH3Br
Molecular Weight: 384.31
Percent Composition: C 56.25%, H 6.82%, N 3.64%, O 12.49%, Br 20.79%
Properties: Crystals, mp 210-212°. Freely sol in water, dil alc; slightly sol in abs alc.
Melting point: mp 210-212°
 
Derivative Type: Sulfate dihydrate
CAS Registry Number: 6835-16-1
Trademarks: Egacene; Egazil Duretter; Peptard (3M Pharma)
Molecular Formula: (C17H23NO3)2.H2SO4.2H2O
Molecular Weight: 712.85
Percent Composition: C 57.29%, H 7.35%, N 3.93%, O 26.93%, S 4.50%
Properties: Needles from alcohol, mp 206° when dry. [a]D15 -29° (c = 2). pH 5.3 (1 in 100). One gram dissolves in 0.5 ml water, about 5.0 ml alcohol. Very slightly sol in chloroform, ether.
Melting point: mp 206° when dry
Optical Rotation: [a]D15 -29° (c = 2)
 
Therap-Cat: Antispasmodic.
Keywords: Antimuscarinic; Antispasmodic.

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