Common NameScopolamine
DescriptionScopolamine, also known as hyoscine, is a tropane alkaloid drug obtained from plants of the family Solanaceae (nightshades), such as henbane or jimson weed (Datura species). It is part of the secondary metabolites of plants. Scopolamine is used criminally as a date rape drug and as an aid to robbery, the most common act being the clandestine drugging of a victim's drink. It is preferred because it induces retrograde amnesia, or an inability to recall events prior to its administration. Victims of this crime are often admitted to a hospital in police custody, under the assumption that the patient is experiencing a psychotic episode. A telltale sign is a fever accompanied by a lack of sweat. 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.
Structure
Molecular FormulaC17H21NO4
Average Mass303.35290
Monoisotopic Mass303.14706
IUPAC Name(1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate
Traditional Name(1r,2r,4s,5s,7s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl (2s)-3-hydroxy-2-phenylpropanoate
CAS Registry Number51-34-3
SMILESCN1[C@@H]2C[C@@H](OC(=O)[C@H](CO)c3ccccc3)C[C@H]1[C@@H]1O[C@@H]12
InChI IdentifierInChI=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/t11-,12-,13-,14+,15-,16+/m1/s1
InChI KeySTECJAGHUSJQJN-FWXGHANASA-N
CHEBI IDCHEBI:16794
HMDB IDHMDB0003573
StateNot Available
Water Solubility6.61e+00 g/l
logP1.40
logS-1.66
pKa (Strongest Acidic)15.15
pKa (Strongest Basic)6.95
Hydrogen Acceptor Count4
Hydrogen Donor Count1
Polar Surface Area62.3 Ų
Rotatable Bond Count5
Physiological Charge0
Formal Charge0
Refractivity79.72 m³·mol⁻¹
Polarizability31.24

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