Homatropine
Title: Homatropine
CAS Registry Number: 87-00-3
CAS Name: endo-(±)-a-Hydroxybenzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
Additional Names: 1aH,5aH-tropan-3a-ol mandelate; mandelyltropeine; tropine mandelate
Molecular Formula: C16H21NO3
Molecular Weight: 275.34
Percent Composition: C 69.79%, H 7.69%, N 5.09%, O 17.43%
Literature 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).
 
Derivative Type: 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.
Melting point: mp 99-100°
 
Derivative Type: DL-Hydrobromide
CAS Registry Number: 51-56-9
Trademarks: Homatrisol (Cooper); Bufopto Homatrocel (Softcon)
Molecular Formula: C16H21NO3.HBr
Molecular Weight: 356.25
Percent Composition: 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.
Melting point: mp ~212° (partial decompn)
 
Derivative Type: DL-Hydrochloride
Molecular Formula: C16H21NO3.HCl
Molecular Weight: 311.80
Percent Composition: 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.
Melting point: mp 217-220° (dec)
 
Derivative Type: DL-Methylbromide
CAS Registry Number: 80-49-9
Trademarks: Arkitropin; Homapin (Mission Pharmacal); Malcotran (Fisons); Mesopin (Endo); Novatrin (Ayerst); Novatropine; Sethyl
Molecular Formula: C16H21NO3.CH3Br
Molecular Weight: 370.28
Percent Composition: 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).
Melting point: mp 191-192° (slight dec)
Toxicity data: LD50 in mice (mg/kg): 1400 orally, 60 i.p. (Cahen, Tvede)
 
Therap-Cat: Mydriatic.
Keywords: Antimuscarinic; Mydriatic.

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