8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-2-phenylacetate hydrobromide

• ChemBase ID: 102516
• Molecular Formular: C16H22BrNO3
• Molecular Mass: 356.25478
• Monoisotopic Mass: 355.07830557
• SMILES: Br.CN1C2CCC1CC(C2)OC(=O)C(O)c1ccccc1
• Canonical SMILES: OC(c1ccccc1)C(=O)OC1CC2CCC(C1)N2C.Br
• InChI: InChI=1S/C16H21NO3.BrH/c1-17-12-7-8-13(17)10-14(9-12)20-16(19)15(18)11-5-3-2-4-6-11;/h2-6,12-15,18H,7-10H2,1H3;1H
• InChIKey: DWSGTFTVBLXELC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-2-phenylacetate hydrobromide
• IUPAC Traditional name: homatropine hydrobromide
• Synonyms: Tropine mandelate hydrobromide; DL-endo-α-Hydroxybenzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester hydrobromide; DL-HOMATROPINE HYDROBROMIDE; α-Hydroxybenzeneacetic Acid (3-Endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl Ester, Hydrobromide; 1αH,5αH-Tropan-3α-ol Mandelate (Ester) Hydrobromide; (±)-Homatropine Bromide; Homatropine bromide; Homatropine Hydrobromide; Isopto Homatropine; Mandelic Acid Tropine Ester Hydrobromide; rac Homatropine Hydrobromide

Database IDs

• CAS Number: 51-56-9
• EC Number: 200-105-3
• PubChem SID: 162090534
• PubChem CID: 5821

CALCULATED PROPERTIES

• Acid pKa: 11.992152
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.757473
• LogD (pH = 7.4): -0.38312137
• Log P: 1.5938674
• Molar Refractivity: 75.8054 cm^3
• Polarizability: 30.19051 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: Room Temperature (15-30°C), Protect from light
• RTECS: YM5602000

DETAILS

MP Biomedicals - 02101968

Hydrobromide
Crystalline
POISONOUS

Toronto Research Chemicals - H459200

Homatropine is an anticholinergic agent. Homatropine acts as an inhibitor of the muscarinic acetylcholine receptors. Homatropine is used in eye drops as a cycloplegic and as a mydriatic, to dilate the pupil.

REFERENCES

• Mattila, M.J. et al.: Ann. Med. Exp. Biol. Fen., 45, 412 (1967)
• Gambill, H. et al.: Arch. Ophthamol., 77, 740 (1967)
• Sund, R.B.: Med. Norsk Farmac. Sels., 33, 143 (1967)