ANISODAMINE

Base Information

• Chemical Name: ANISODAMINE
• CAS No.: 17659-49-3
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374
• Hs Code.: 29399990
• European Community (EC) Number: 637-239-0
• NSC Number: 755866
• DSSTox Substance ID: DTXSID00425118
• Wikipedia: Anisodamine
• Mol file: 17659-49-3.mol

Synonyms:Raceanisodamine;

Chemical Property of ANISODAMINE

Chemical Property:

• Appearance/Colour: No Data Available
• Melting Point: No Data Available
• Boiling Point: No Data Available
• PKA: 14.12±0.10(Predicted)
• PSA: 70.00000
• Density: 1.27
• LogP: 0.83960
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 305.16270821
• Heavy Atom Count: 22
• Complexity: 396

Purity/Quality:

99% ^*data from raw suppliers

Racanisodamine 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CC(CC1C(C2)O)OC(=O)C(CO)C3=CC=CC=C3
• Isomeric SMILES: CN1[C@H]2C[C@H](CC1C[C@@H]2O)OC(=O)[C@H](CO)C3=CC=CC=C3
• Recent ClinicalTrials: FOLFOX Via HAI Plus Intravenous Irinotecan With or Without Bevacizumab Versus Systemic FOLFOXIRI With or Without Bevacizumab in Initially Unresectable RAS-mutated CRLM Patients
• Description: Amisodamine is a kind of alkaloid which is mainly living in anisodus tanguticus, which is a M receptor just like Atropine. It is a kind of traditional Chinese medicine which comes from the “National assembly of Chinese Herbal medicine”, and it is the alias of zangjia registered in “Chines herbal medicine summary of shan gan ning qing”. It is a perennial root herb that lives in the bottom slope in the eastern Tibet, Qinghai Province, the Southern GanSu Province, the western SiChuan Province, the northwestward YunNan Province. Since the sources is scare, racemic form of raceanisodamine is the main drug in clinic. Anisodamine is a natural tropane alkaloid shown to be a weak antagonist of α1-adrenoceptors, blocking WB-4101 and clonidine binding in brain membrane preparations with pKi values of 2.63 and 1.61, respectively. Anisodamine also has antioxidant effects that may protect against free radical-induced cellular damage. Anisodamine is predominantly found in the roots of A. tanguticus, which is used in traditional Chinese medicine for topical applications.
• Physical properties: Appearance: raceanisodamine is a kind of white crystal and crystalline powder. It is odorless and bitter to the taste. Solubility: it is easy dissolubility in hydrochloric acid and ethyl alcohol and is soluble in water. Melting point: it’s melting point is from 103 to 113?°C.?The weld spacing is within 6°. Specific optical rotation: ?9° to +11°.
• Uses: anticholinergic, antispasmodic Tropic Acid 6-Hydroxy-3-tropanyl Ester is a Hycosamine (H674300) derivative, which is a natural compound with inhibitory activity against cholinesterases.
• Indications: Anisodamine is a kind of anticholinergic agent. The tablet and injection form are mainly used to relieve smooth muscle spasm, biliary spasm and AOIP in clinical practice. The eye drop is used to treat teenage pseudomyopia; raceanisodamine concomitant with other drugs to treat cluster headache syndrome, renal colic, infantile diarrhea, infantile jaundice hepatitis, infantile purpura, bronchopneumonia, etc.
• Clinical Use: Anisodamine is a new drug developed by Chinese scientists. It has been widely put into use in clinical practice such as slow reflow phenomenon of ST-elevation acute myocardial infarction patients with percutaneous coronary intervention, infusion leakage , neonatal sclerosis. At present, it is mainly used to dilate vessels, remove vasospasm, improve blood circulation, increase tolerance of ischemia hypoxia and reduce the probability of the surrounding tissue necrosis

Technology Process of ANISODAMINE

There total 26 articles about ANISODAMINE 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:

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:

(-)-hyoscyamine hydrobromide (6415-90-3,50700-39-5,306-03-6,4607-53-8) → (-)-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)

Guidance literature:

With α-ketoglutaric acid; Anisodus tanguticus hyoscyamine 6β-hydroxylase; iron(II) sulfate; In various solvent(s); at 30 ℃; for 2h; pH=7.4; Enzyme kinetics;

DOI:10.1055/s-2005-837825

Reference yield:

(1R,3S,5S)-8-methyl[6β-2H]-8-azabicyclo[3.2.1]octan-3-ol → C17H22(2)HNO4 + (-)-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)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; camphor-10-sulfonic acid; dicyclohexyl-carbodiimide / dichloromethane / 72 h / 20 °C

2: hydrogenchloride; water / methanol / 20 °C

3: hyoscyamine 6β-hydroxylase; iron(II) sulfate; α-ketoglutaric acid; sodium L-ascorbate / aq. buffer / 0.5 h / 20 °C / pH 6.9 / Enzymatic reaction

With hydrogenchloride; dmap; α-ketoglutaric acid; camphor-10-sulfonic acid; hyoscyamine 6β-hydroxylase; water; iron(II) sulfate; sodium L-ascorbate; dicyclohexyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1021/jacs.8b11585

upstream raw materials:

scopolamine

(-)-hyoscyamine hydrobromide

(2S,3S)-di-4-toluoyltartaric acid

C₁₅H₂₇NO₃Si

Downstream raw materials:

(3R,6R)-tropane-3α,6β-diol

scopolamine

(S)-tropic acid

3α,6β-dihydroxytropane HCl

Refernces

• 1、 Ushimaru, Richiro,Ruszczycky, Mark W.,Liu, Hung-Wen. "Changes in Regioselectivity of H Atom Abstraction during the Hydroxylation and Cyclization Reactions Catalyzed by Hyoscyamine 6β-Hydroxylase". . p. 1062 - 1066. Retrieved 2019/01/23.
• 2、 Li, Jing,Van Belkum, Marco J.,Vederas, John C.. "Functional characterization of recombinant hyoscyamine 6β-hydroxylase from Atropa belladonna". experimental part. p. 4356 - 4363. Retrieved 2012/08/28.