4730. Homatropine

Nomenclature

CAS number: 87-00-3
endo-(±)-α-Hydroxybenzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester; 1αH,5αH-tropan-3α-ol mandelate; mandelyltropeine; tropine mandelate.
C16H21NO3; mol wt 275.34.
C 69.79%, H 7.69%, N 5.09%, O 17.43%.

Description and references

Ophthalmic anticholinergic. Prepd from mandelic acid and tropine: Ladenburg, Ann. 217, 82 (1883); Chemnitius, J. Prakt. Chem. 117, 142 (1927). Prepn of d()- and l(+)-forms: Werner, Miltenberger, Ann. 631, 163 (1960). Comprehensive description: F. J. Muhtadi et al., Anal. Profiles Drug Subs. 16, 245-290 (1987). Toxicity: R. L. Cahen, K. Tvede, J. Pharmacol. Exp. Ther. 105, 166 (1952).

Chemical structure

Derivative

dl-Form.

Properties

Prisms from ether, mp 99-100°. Poisonous. Hygroscopic, but only slightly sol in water; sol in alcohol, benzene, chloroform, ether, acetone, dil acids.

Derivative

dl-Hydrobromide.

Nomenclature

CAS number: 51-56-9
Homatrisol (Cooper); Bufopto Homatrocel (Softcon).
C16H21NO3.HBr; mol wt 356.25.
C 53.94%, H 6.22%, N 3.93%, O 13.47%, Br 22.43%.

Properties

Orthorhombic, bipyramidal prisms from water, mp ≈212° (partial decompn). Poisonous. One gram dissolves in 6 ml water, 40 ml alcohol (12 ml at 60°), 420 ml chloroform. Insol in ether. pH (1% aq soln): 5.4.

Derivative

dl-Hydrochloride.
C16H21NO3.HCl; mol wt 311.80.
C 61.63%, H 7.11%, N 4.49%, O 15.39%, Cl 11.37%.

Properties

Prisms from water, mp 217-220° (dec). Poisonous. Freely sol in water, alcohol. pH (1% aq soln): 5.4.

Derivative

dl-Methylbromide.

Nomenclature

CAS number: 80-49-9
Arkitropin; Homapin (Mission Pharmacal); Malcotran (Fisons); Mesopin (Endo); Novatrin (Ayerst); Novatropine; Sethyl.
C16H21NO3.CH3Br; mol wt 370.28.
C 55.14%, H 6.53%, N 3.78%, O 12.96%, Br 21.58%.

Properties

Minute needles from alc + ether, mp 191-192° (slight dec). Poisonous. Freely sol in water, dil alc; slightly sol in abs alc. Insol in ether. pH (1% aq soln) 5.9; pH (10% aq soln) 4.5. LD50 in mice (mg/kg): 1400 orally, 60 i.p. (Cahen, Tvede).

Therapeutic Category

Mydriatic.

Keywords

Antimuscarinic; Mydriatic