Scopalamine

Base Information

• Chemical Name: Scopalamine
• CAS No.: 138-12-5
• Molecular Formula: C17H21NO4
• Molecular Weight: 303.358
• European Community (EC) Number: 200-090-3
• DSSTox Substance ID: DTXSID8043812
• Nikkaji Number: J154.072F,J47.151H,J698.389H
• Wikipedia: Scopolamine
• Wikidata: Q104391779
• NCI Thesaurus Code: C47712
• RXCUI: 9601
• Mol file: 138-12-5.mol

Synonyms:Boro Scopol;Boro-Scopol;Hyoscine;Isopto Hyoscine;Kwells;Scoburen;Scopace;Scopoderm TTS;Scopolamine;Scopolamine Cooper;Scopolamine Hydrobromide;Transderm Scop;Transderm V;Transderm-V;Travacalm HO;Vorigeno

Chemical Property of Scopalamine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: ?15?°C(lit.)
• Refractive Index: 1.614
• Boiling Point: 460.3 °C at 760 mmHg
• PKA: 14.11±0.10(Predicted)
• Flash Point: 232.2 °C
• PSA: 62.30000
• Density: 1.31 g/cm³
• LogP: 0.85600
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 303.14705815
• Heavy Atom Count: 22
• Complexity: 418

Purity/Quality:

99%, ^*data from raw suppliers

Hyoscine European Pharmacopoeia (EP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CC(CC1C3C2O3)OC(=O)C(CO)C4=CC=CC=C4
• Isomeric SMILES: CN1[C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)OC(=O)C(CO)C4=CC=CC=C4
• Recent ClinicalTrials: Prevention and Treatment of Nausea Associated With Motion Sickness in Senior Subjects
• Recent EU Clinical Trials: A single blind study comparing the efficacy of Glycopyrronium and Hyoscine on drooling in children with neurodisability - DRI Trial (Drooling Reduction Intervention)
• Recent NIPH Clinical Trials: Study of the upper gastrointestinal tract peristalsis inhibitory effect of acupuncture in endoscopic submucosal dissection for early gastric cancer: A randomized controlled trial.

Technology Process of Scopalamine

There total 28 articles about Scopalamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 16.0%

8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl 3-hydroxy-2-phenylpropanoate → (+/-)-scopolamine (51-34-3,138-12-5,64069-63-2,124917-17-5)

Guidance literature:

With formic acid; dihydrogen peroxide; at 20 ℃; for 72h;

DOI:10.1002/ejoc.201501430

Reference yield:

(αS)-α-(hydroxymethyl)benzeneacetic acid (endo)-8-methyl8-azabicyclo[3.2.1]oct-6-en-3-yl ester (22150-33-0,54725-48-3,61616-97-5) → scopolamine (51-34-3,138-12-5,64069-63-2,124917-17-5)

Guidance literature:

With α-ketoglutaric acid; Atropa belladonna C-terminally hexahistidine-tagged hyoscyamine 6β-hydroxylase; iron(II) sulfate; sodium L-ascorbate; catalase; pH=7.6; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.bmc.2012.05.042

Reference yield:

hyoscine hydrobromide (114-49-8) → scopolamine (51-34-3,138-12-5,64069-63-2,124917-17-5)

Guidance literature:

With sodium carbonate; In water; ethyl acetate; at 0 ℃; for 0.25h; Reagent/catalyst;

DOI:10.1002/jlcr.3463

upstream raw materials:

(-)-Anisodamine

oxytropium bromide

(αS)-α-(hydroxymethyl)benzeneacetic acid (endo)-8-methyl8-azabicyclo[3.2.1]oct-6-en-3-yl ester

hyoscine hydrobromide

Downstream raw materials:

8ξ-ethyl-6exo,7exo-epoxy-8ξ-methyl-L-3-tropoyloxy-nortropanium; iodide

7t-(3-hydroxy-2-phenyl-propionyloxy)-9,9-dimethyl-(1rN,2tH,4tH,5cN)-3-oxa-9-aza-tricyclo[3.3.1.0^2,4]nonanium; iodide

Tropic acid

(S)-tropic acid

Refernces

• 1、 Latli, Bachir,Stiasni, Michael,Hrapchak, Matt,Li, Zhibin,Grinberg, Nelu,Lee, Heewon,Busacca, Carl A.,Senanayake, Chris H.. "Buscopan labeled with carbon-14 and deuterium". . p. 557 - 564. Retrieved 2016/11/23.
• 2、 Nocquet, Pierre-Antoine,Opatz, Till. "Total Synthesis of (±)-Scopolamine: Challenges of the Tropane Ring". . p. 1156 - 1164. Retrieved 2016/03/05.