Transderm-V

Base Information

• Chemical Name: Transderm-V
• CAS No.: 51-34-3
• Molecular Formula: C17H21NO4
• Molecular Weight: 303.35
• Hs Code.: 29399990
• European Community (EC) Number: 200-090-3
• Wikipedia: Scopolamine
• Wikidata: Q105260183
• NCI Thesaurus Code: C47712
• RXCUI: 9601
• Mol file: 51-34-3.mol

Synonyms:scopolamine;(-)-Scopolamine;Atroscine;Transderm-V;HSDB 4074;EINECS 200-090-3;tropic acid ester with scopine;D0RY4M;6-beta,7-beta-epoxy-1-alpha H,5-alpha H-tropan-3-alpha-ol (-)-tropate;138-12-5;51-34-3;Benzeneacetic acid, alpha-(hydroxymethyl)-, (1alpha,2beta,4beta,5alpha,7beta)-9-methyl-3-oxa-9-azatricyclo(3.3.1.02,4)non-7-yl ester, (alphaS)-;Benzeneacetic acid, alpha-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo(3.3.1.02,4)non-7-yl ester, (7(S)-(1alpha,2beta,4beta,5alpha,7beta))-;LS-144659

Chemical Property of Transderm-V

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 59 °C
• Refractive Index: 1.5022 (estimate)
• Boiling Point: 460.313 °C at 760 mmHg
• PKA: 7.55-7.81(at 25℃)
• Flash Point: 232.189 °C
• PSA: 62.30000
• Density: 1.313 g/cm³
• LogP: 0.85600
• Storage Temp.: -20°C
• Solubility.: Soluble in water, freely soluble in ethanol (96 per cent).
• Water Solubility.: 95g/L(15 oC)
• 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

Scopolamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 25-45

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: Efficacy and Safety of Escócia Association in the Treatment of Acute Pain
• 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)
• Description: Scopolamine is a type of alkaloid that exists in a variety of Solanaceae plants such as Scopolia japonica, Datura metel L., and so on. It is the main active ingredient in these plants.Apart from scopolamine, several other chemical ingredients also exist in Scopolia japonica, including hyoscyamine, anisodamine, anisodine, and so on. Hyoscyamine is an inhibitor of parasympathetic nerve, with the analgesic and antispasmodic functions, especially for sciatica, sometimes for the treatment of epilepsy, seasickness, etc., and its pharmacological effects are similar to atropine. However, its clinical application is less because of its toxicity. The clinical applications of anisodamine are treating infectious toxic shock, vascular disorders, various neuralgia, smooth muscle spasms, vertigo, fundus disorders and sudden deafness, and other diseases. It has definite curative effect and is widely used in clinical in China. Its synthetic product is called “654-2,” which now still is an effective drug to treat infectious shock and other vascular diseases. While anisodine is used to treat vascular headache, retinal vasospasm, ischemic optic neuritis, cerebrovascular disease, acute paralysis, central dysfunction caused by carbon monoxide poisoning, tremor, paralysis, bronchial asthma, motion sickness, organophosphorus pesticide poisoning, and so on .
• Physical properties: Appearance: a kind of viscous liquid, brown color. Solubility: soluble in ethanol, ethyl ether, chloroform, acetone, and water, very soluble in hot water, slightly soluble in benzene and petroleum ether, and also soluble in cold water. It can generate various crystals with multiple inorganic or organic acids. Melting point: 59±1.0?°C
• Uses: Scopolamine is used for practically the same indications as atropine, but it should be noted that it has a sedative effect on motor activity, and it is recommended for the treatment of Parkinsonian symptoms. cholinergic (ophthalmic).
• Clinical Use: The commercially available transdermal system of scopolaminecomprises an outer layer of polymer film and a drug reservoircontaining scopolamine, polyisobutylene, and mineral oil, which is interfaced with a microporous membrane tocontrol diffusion of the drug. In this dosage form, scopolamineis effective in preventing motion sickness. The actionis believed to be on the cortex or the vestibular apparatus.Whereas atropine stimulates the CNS, causing restlessnessand talkativeness, scopolamine usually acts as a CNSdepressant.

Technology Process of Transderm-V

There total 28 articles about Transderm-V 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.