8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2S)-3-hydroxy-2-phenylpropanoate

• ChemBase ID: 307
• Molecular Formular: C17H23NO3
• Molecular Mass: 289.36942
• Monoisotopic Mass: 289.1677936
• SMILES: O(C1CC2N(C(CC2)C1)C)C(=O)[C@@H](c1ccccc1)CO
• Canonical SMILES: OC[C@H](c1ccccc1)C(=O)OC1CC2CCC(C1)N2C
• InChI: InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13?,14?,15?,16-/m1/s1
• InChIKey: RKUNBYITZUJHSG-LGGPCSOHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2S)-3-hydroxy-2-phenylpropanoate
• IUPAC Traditional name: hyoscyamine; levbid
• Brand Name: Anaspaz; Cystospaz; Daturine; Duboisine; Duretter; Egacene; Egazil; Gastrosed; Levbid; Levsin; Levsinex; OIN; Peptard; Scopolia Extract; Symax; Buwecon; Donnamar; NuLev; Neoquess
• Synonyms: L-Tropine Tropate; L-Hyoscyamine; L-Hyoscamine; L-Hyopscyamine; L-Atropine; Hyocyamine; Hyoscyamine; Daturine; Hyoscyamine; (-)-Tropic Acid Ester with Tropine; L-HYOSCYAMINE

Database IDs

• CAS Number: 101-31-5
• EC Number: 202-933-0
• PubChem SID: 160963770
• PubChem CID: 64692

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.1457405
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.7801015
• LogD (pH = 7.4): -0.40574417
• Log P: 1.571241
• Molar Refractivity: 80.8164 cm^3
• Polarizability: 32.034832 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.19
• LOG S: -2.06
• Solubility (Water): 2.52e+00 g/l

PROPERTIES

Physical Property

• Solubility: 3.56 mg/mL
• Melting Point: 106-108.5°C
• Hydrophobicity(logP): 1.8

Safety Information

• Storage Condition: 2-8°C
• RTECS: NH0875000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: R:26/28
• Safety Statements: S:24-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154

DETAILS

MP Biomedicals - 02151316

Free Base Crystalline

DrugBank - DB00424

• Drug Groups: approved
• Description: Hyoscyamine is a chemical compound, a tropane alkaloid it is the levo-isomer to atropine. It is a secondary metabolite of some plants, particularly henbane (Hyoscamus niger.); Hyoscyamine is used to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinson's disease, as well as for control of respiratory secretions in end of life care.
• Indication: For treatment of bladder spasms, peptic ulcer disease, diverticulitis, colic, irritable bowel syndrome, cystitis, and pancreatitis. Also used to treat certain heart conditions, to control the symptoms of Parkinson's disease and rhinitis.
• Pharmacology: L-Hyoscyamine, the active optical isomer of atropine (dl-hyoscyamine), is a tertiary amine anticholinergic gastrointestinal agent.
• Toxicity: Symptoms of overdose include headache, nausea, vomiting, blurred vision, dilated pupils, hot dry skin, dizziness, dryness of the mouth, difficulty in swallowing, and CNS stimulation. LD₅₀=mg/kg(orally in rat)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Absorbed totally and completely by sublingual administration as well as oral administration.
• Half Life: 2-3.5 hours
• Protein Binding: 50%
• External Links: Wikipedia; RxList; Drugs.com