(S)-((1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate

Base Information

• Chemical Name: (S)-((1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate
• CAS No.: 101-31-5
• Molecular Formula: C17H23NO3
• Molecular Weight: 289.375
• Hs Code.: 29339900
• European Community (EC) Number: 202-933-0
• Wikipedia: Hyoscyamine
• Wikidata: Q104252704
• NCI Thesaurus Code: C29104
• RXCUI: 153970
• ChEMBL ID: CHEMBL1257084
• Mol file: 101-31-5.mol

Synonyms:Anaspaz;Atropine Sulfate, 3(S)-endo-Isomer;Atropine, 3(S)-endo-Isomer;Cytospaz;Hyoscyamine;Hyoscyamine Hydrobromide;Hyoscyamine Hydrochloride;Hyoscyamine Sulfate;Hyoscyamine Sulfate Anhydrous

Chemical Property of (S)-((1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 108.5 °C
• Refractive Index: 1.581
• Boiling Point: 429.804 °C at 760 mmHg
• PKA: pKa (21°) 9.7
• Flash Point: 213.738 °C
• PSA: 49.77000
• Density: 1.194 g/cm³
• LogP: 1.86880
• Storage Temp.: 2-8°C
• Water Solubility.: 3.6g/L(20 oC)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 289.16779360
• Heavy Atom Count: 21
• Complexity: 353

Purity/Quality:

≥98% ^*data from raw suppliers

(-)-Hycosamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/28
• Safety Statements: 24-45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Gastrointestinal Agents
• Canonical SMILES: CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
• Isomeric SMILES: CN1[C@H]2CC[C@H]1CC(C2)OC(=O)[C@H](CO)C3=CC=CC=C3
• Recent ClinicalTrials: Efficacy of Open Label Placebo in Children With FGIDs
• Uses: L-Hyoscyamine is a natural compound that has inhibitory activity against cholinesterases. L-Hyoscyamine can be used as anticholinergic and analgesic. Suggested starting dilutions are as follows: IHC-P: 1:100-1:1000, WB: 1:1000-1:10000. Not yet tested in other applications. Optimal working dilutions should be determined experimentally by the end user.
• Clinical Use: (L-Hyoscyamine)Hyoscyamine is used to treat disorders of the urinarytract more so than any other antispasmodic, although thereis no evidence that it has any advantages over the otherbelladonna preparations and the synthetic anticholinergics.It is used to treat spasms of the bladder and, in this manner,serves as a urinary stimulant. It is used together witha narcotic to counteract the spasm produced by the narcoticwhen the latter is used to relieve the pain of urethral colic.Hyoscyamine preparations are also used as antispasmodicsin the therapy of peptic ulcers.

Technology Process of (S)-((1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate

There total 18 articles about (S)-((1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate 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: 41.7%

hyoscine hydrobromide (114-49-8) → (3S,6S,2'S)-6β-hydroxyhyoscyamine (55869-99-3) + (3R,6R,2'S)-6β-hydroxyhyoscyamine (126371-43-5) + Hyoscyamine (101-31-5)

Guidance literature:

With hydrogen; Nickel Raney W₁;

DOI:10.1021/np060133j

Reference yield:

scopolamine (51-34-3,138-12-5,64069-63-2,124917-17-5) → (-)-Anisodamine (17659-49-3,32671-33-3,76831-52-2,85760-60-7,126371-43-5,134355-54-7,138876-55-8,55869-99-3) + 7b-Hydroxyhyoscyamine (126371-43-5) + Hyoscyamine (101-31-5)

Guidance literature:

With hydrogen; nickel; In water; at 20 ℃; for 19h;

DOI:10.1016/0031-9422(89)80374-7

Reference yield:

Atropine (51-55-8) → (+)-Atropine (13269-35-7) + Hyoscyamine (101-31-5)

Guidance literature:

With β?cyclodextrin sulfonic acid; In aq. phosphate buffer; at 25 ℃; pH=3; pH-value; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/chir.22731

upstream raw materials:

(S)-tropic acid

3-tropanol

(1S)-10-camphorsulfonic acid

atropine

Downstream raw materials:

atropine

apoatropine

(+/-)-1-phenyl-1,2,3,4-tetrahydro-naphthalene-1r,4t-dicarboxylic acid di-tropane-3endo-yl ester

3β-O-(hyoscaminioacetyl)strophantidin bromide

Refernces

• 1、 Okamoto, Yoshio,Sakamoto, Hideaki,Hatada, Koichi,Irie, Masahiro. "RESOLUTION OF ENANTIOMERS BY HPLC ON CELLULOSE TRANS- AND CIS-TRIS(4-PHENYLAZOPHENYLCARBAMATE)". . p. 983 - 986. Retrieved 1986.
• 2、 Zaazaa, Hala E.,Salama, Nahla N.,Abd El Halim, Lobna M.,Salem, Maissa Y.,Abd El Fattah, Laila E.. "Strategy Approach for Direct Enantioseparation of Hyoscyamine Sulfate and Zopiclone on a Chiral αl-Acid Glycoprotein Column and Determination of Their Eutomers: Thermodynamic Study of Complexation". . p. 49 - 57. Retrieved 2016.
• 3、 Barrowcliff,Tutin. "-". . p. 1966. Retrieved 1909.
• 4、 -. "ALKOXY ARYL BETA2 ADRENERGIC RECEPTOR AGONISTS". . . Retrieved 2008/06/13.