4858. Hyoscyamine

Nomenclature

CAS number: 101-31-5
[3(S)-endo]-α-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester; 1αH,5αH-tropan-3α-ol()-tropate (ester); 3α-tropanyl S-()-tropate; l-tropic acid ester with tropine; l-tropine tropate; daturine; duboisine; l-hyoscyamine; Cystospaz (Alcon); Levsin (Kremers-Urban).
C17H23NO3; mol wt 289.37.
C 70.56%, H 8.01%, N 4.84%, O 16.59%.

Description and 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).

Chemical structure

Properties

Silky, tetragonal needles from evaporating alc. Keep well closed and protect from light and heat; easily racemized. mp 108.5°. [α]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).

Derivative

Hydrobromide.

Nomenclature

CAS number: 306-03-6
C17H23NO3.HBr; mol wt 370.28.
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.

Derivative

Hydrochloride.
C17H23NO3.HCl; mol wt 325.83.
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.

Derivative

Methyl bromide.

Nomenclature

N-Methylhyoscyaminium bromide.
C17H23NO3.CH3Br; mol wt 384.31.
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.

Derivative

Sulfate dihydrate.

Nomenclature

CAS number: 6835-16-1
Egacene; Egazil Duretter; Peptard (3M Pharma).
(C17H23NO3)2.H2SO4.2H2O; mol wt 712.85.
C 57.29%, H 7.35%, N 3.93%, O 26.93%, S 4.50%.

Properties

Needles from alcohol, mp 206° when dry. [α]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.

Therapeutic Category

Antispasmodic.

Keywords

Antimuscarinic; Antispasmodic