Inquiry Basket
Apohyoscine
Apohyoscine is a bioactive substance isolated from Datura ferox and several algae genera (Physochlaina). Apohyoscine is a tropane alkaloid and a derivative of scopolamine, also known as hyoscine. It is structurally related to hyoscine but lacks some of the functional groups present in the parent compound, making it an ''apo'' derivative. Apohyoscine retains some pharmacological activity, particularly as an anticholinergic agent, meaning it can block the action of acetylcholine in the nervous system. However, it is less commonly used than scopolamine itself, which is widely used for its antiemetic and antispasmodic properties, such as in the treatment of motion sickness and postoperative nausea.
* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.
Catalog
BRP-02096
Synonyms
α-Methylenebenzeneacetic Acid (1α,2β,4β,5α,7β)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl Ester; Aposcopolamin; Benzeneacetic acid, α-methylene-, (1α,2β,4β,5α,7β)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester; 1αH,5αH-Tropan-3α-ol, 6β,7β-epoxy-, atropate (ester); Aposcopolamine; Benzeneacetic acid, α-methylene-, 9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester, (1α,2β,4β,5α,7β)-; Aposcopolamin
CAS
535-26-2
IUPAC Name
(1R,2R,4S,5S,7s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl 2-phenylacrylate
Molecular Weight
285.34
Molecular Formula
C17H19NO3
Canonical SMILES
O=C(OC1CC2N(C)C(C1)C3OC32)C(=C)C=4C=CC=CC4
InChI
InChI=1/C17H19NO3/c1-10(11-6-4-3-5-7-11)17(19)20-12-8-13-15-16(21-15)14(9-12)18(13)2/h3-7,12-16H,1,8-9H2,2H3/t12-,13-,14+,15-,16+
InChIKey
JJNVDCBKBUSUII-JGPUMOJJNA-N
Boiling Point
415.5±45.0 °C at 760 mmHg
Melting Point
96-98 °C
Purity
>95%
Density
1.25±0.1 g/cm3 at 20 °C, 760 Torr
Solubility
Soluble in DMSO
Appearance
Off-White to Pale Yellow Solid
Storage
Store at -20 °C
Chemical Structure:
Reference Reading
1.Quantitative microtiter fibronectin fibrillogenesis assay: use in high throughput screening for identification of inhibitor compounds.
Tomasini-Johansson BR1, Johnson IA, Hoffmann FM, Mosher DF. Matrix Biol. 2012 Jul;31(6):360-7. doi: 10.1016/j.matbio.2012.07.003. Epub 2012 Aug 6.
Fibronectin (FN) is a plasma glycoprotein that circulates in the near micromolar concentration range and is deposited along with locally produced FN in the extracellular matrices of many tissues. The control of FN deposition is tightly controlled by cells. Agents that modulate FN assembly may be useful therapeutically in conditions characterized by excessive FN deposition, such as fibrosis, inflammatory diseases, and malignancies. To identify such agents by high throughput screening (HTS), we developed a microtiter assay of FN deposition by human fibroblasts. The assay provides a robust read-out of FN assembly. Alexa 488-FN (A488-FN) was added to cell monolayers, and the total fluorescence intensity of deposited A488-FN was quantified. The fluorescence intensity of deposited A488-FN correlated with the presence of FN fibrils visualized by fluorescence microscopy. The assay Z' values were 0.67 or 0.54, respectively, when using background values of fluorescence either with no added A488-FN or with A488-FN added together with a known inhibitor of FN deposition.
2.Metabolism in vivo of the tropane alkaloid, scopolamine, in several mammalian species.
Wada S1, Yoshimitsu T, Koga N, Yamada H, Oguri K, Yoshimura H. Xenobiotica. 1991 Oct;21(10):1289-300.
1. In vivo metabolism of scopolamine was studied in rats, mice, guinea pigs and rabbits. The structures of eight urinary metabolites including unchanged drug were elucidated by mass and nuclear magnetic resonance spectrometry. Determination of these metabolites was achieved by a g.l.c. method using a semi-capillary column. 2. The major metabolites in rats were the three phenolic metabolites, p-hydroxy-, m-hydroxy- and p-hydroxy-m-methoxy-scopolamine. 3. Significant intra-species difference of the metabolism was observed in rabbits. Tropic acid was the major metabolite in two rabbits out of three, while the other rabbit excreted mainly unchanged scopolamine, accompanied by five metabolites. Tropic acid was also the major metabolite in guinea pigs, but was of minor importance in mice. 4. The dehydrated metabolites, aposcopolamine and aponorscopolamine, were abundantly excreted in guinea pigs, moderately in mice, and least in rabbits and rats.
3.Analysis of scopolamine and its eighteen metabolites in rat urine by liquid chromatography-tandem mass spectrometry.
Chen H1, Chen Y, Wang H, Du P, Han F, Zhang H. Talanta. 2005 Oct 31;67(5):984-91. doi: 10.1016/j.talanta.2005.04.026.
A rapid and sensitive method is described for the determination of scopolamine and its metabolites in rat urine by combining liquid chromatography and tandem mass spectrometry (LC-MS/MS). Various extraction techniques (free fraction, acid hydrolyses and enzyme hydrolyses) and their comparison were carried out for investigation of the metabolism of scopolamine. After extraction procedure, the pretreated samples were injected into a reversed-phase C18 column with mobile phase of methanol/ ammonium acetate (2mM, adjusted to pH 3.5 with formic acid) (70:30, v/v) and detected by an on-line MS/MS system. Identification and structural elucidation of the metabolites were performed by comparing their changes in molecular masses (DeltaM), retention-times and full scan MS(n) spectra with those of the parent drug. The results revealed that at least 18 metabolites (norscopine, scopine, tropic acid, aponorscopolamine, aposcopolamine, norscopolamine, hydroxyscopolamine, hydroxyscopolamine N-oxide, p-hydroxy-m-methoxyscopolamine, trihydroxyscopolamine, dihydroxy-methoxyscopolamine, hydroxyl-dimethoxyscopolamine, glucuronide conjugates and sulfate conjugates of norscopolamine, hydroxyscopolamine and the parent drug) and the parent drug existed in urine after ingesting 55mg/kg scopolamine to healthy rats.
4.Liquid chromatographic determination of hyoscine (scopolamine) in urine using solid phase extraction.
Whelpton R1, Hurst PR, Metcalfe RF, Saunders SA. Biomed Chromatogr. 1992 Jul-Aug;6(4):198-204.
A sensitive method for the determination of hyoscine (scopolamine) in urine is described. After concentration and "clean-up" on C18 and CN solid phase extraction columns, hyoscine was quantified by high performance liquid chromatography with coulometric detection (oxidation at +0.9 V). The limit of detection was 5 ng per sample and the precision for 5 mL samples containing 2 ng/mL was 12.3%. The method was applied to urine samples collected from 12 volunteers wearing Scopoderm TTS patches. The mean excretion rate of unmetabolized hyoscine was 0.45 micrograms/h and 87% of the total hyoscine was present as conjugates. Apohyoscine (aposcopolamine) was identified as a urinary metabolite. The significance of this with regard to hyoscine assays is discussed.
