9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl 3-hydroxy-2-phenylpropanoate

• ChemBase ID: 627
• Molecular Formular: C17H21NO4
• Molecular Mass: 303.35294
• Monoisotopic Mass: 303.14705816
• SMILES: O1C2C1C1N(C2CC(OC(=O)C(CO)c2ccccc2)C1)C
• Canonical SMILES: OCC(c1ccccc1)C(=O)OC1CC2N(C(C1)C1C2O1)C
• InChI: InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3
• InChIKey: STECJAGHUSJQJN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl 3-hydroxy-2-phenylpropanoate
• IUPAC Traditional name: scopolamine
• Brand Name: Atrochin; Atroquin; Atroscine Hydrobromide; Beldavrin; Buscopan; Epoxytropine Tropate; Euscopol; Hydroscine Hydrobromide; Hyocine F Hydrobromide; Hyosceine; Hyoscine; Hyoscine Bromide; Hyoscine Hydrobromide; Hyoscyine Hydrobromide; Hyosol; Hysco; Isopto Hyoscine; Isoscopil; Kwells; L-Hyoscine Hydrobromide; L-Scopolamine; Methscopolamine Bromide; Oscine; SEE; Scop; Scopamin; Scopine Tropate; Scopoderm-Tts; Scopolamine Bromide; Scopolamine Hydrobromide; Scopolamine Hydrobromide Trihydrate; Scopolamine Hyoscine; Scopolaminhydrobromid; Scopolaminium Bromide; Scopolammonium Bromide; Scopos; Sereen; Skopolamin; Tranaxine; Transcop; Transderm-Scop; Transderm-V; Triptone; Tropic Acid, Ester with Scopine
• Synonyms: Scopolamine

Database IDs

• CAS Number: 51-34-3
• PubChem SID: 160964090
• PubChem CID: 5184

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.14574
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.56972116
• LogD (pH = 7.4): 0.7621961
• Log P: 0.8949523
• Molar Refractivity: 79.7213 cm^3
• Polarizability: 32.014694 Å^3
• Polar Surface Area: 62.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.4
• LOG S: -1.66
• Solubility (Water): 6.61e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 0.8

DETAILS

DrugBank - DB00747

• Drug Groups: approved
• Description: An alkaloid from Solanaceae, especially Datura metel L. and Scopola carniolica. Scopolamine and its quaternary derivatives act as antimuscarinics like atropine, but may have more central nervous system effects. Among the many uses are as an anesthetic premedication, in urinary incontinence, in motion sickness, as an antispasmodic, and as a mydriatic and cycloplegic. [PubChem]
• Indication: For the treatment of excessive salivation, colicky abdominal pain, bradycardia, sialorrhoea, diverticulitis, irritable bowel syndrome and motion sickness.
• Pharmacology: Scopolamine is a muscarinic antagonist structurally similar to the neurotransmitter acetylcholine and acts by blocking the muscarinic acetylcholine receptors and is thus classified as an anticholinergic. Scopolamine has many uses including the prevention of motion sickness. It is not clear how Scopolamine prevents nausea and vomiting due to motion sickness. The vestibular part of the ear is very important for balance. When a person becomes disoriented due to motion, the vestibule sends a signal through nerves to the vomiting center in the brain, and vomiting occurs. Acetylcholine is a chemical that nerves use to transmit messages to each other. It is believe that Scopolamine prevents communication between the nerves of the vestibule and the vomiting center in the brain by blocking the action of acetylcholine. Scopolamine also may work directly on the vomiting center. Scopolamine must be taken before the onset of motion sickness to be effective.
• Affected Organisms: Humans and other mammals
• Absorption: Bioavailability is 10 - 50%
• Half Life: 4.5 hours
• Elimination: Less than 10% of the total dose is excreted in the urine as parent and metabolites over 108 hours.
• References: Putcha L, Cintron NM, Tsui J, Vanderploeg JM, Kramer WG: Pharmacokinetics and oral bioavailability of scopolamine in normal subjects. Pharm Res. 1989 Jun;6(6):481-5. [Pubmed]
• External Links: Wikipedia; Drugs.com

REFERENCES

• Putcha L, Cintron NM, Tsui J, Vanderploeg JM, Kramer WG: Pharmacokinetics and oral bioavailability of scopolamine in normal subjects. Pharm Res. 1989 Jun;6(6):481-5. Pubmed