Anisodamine - CAS 55869-99-3
Catalog number:
55869-99-3
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C17H23NO4
Molecular Weight:
305.37
COA:
Inquire
Targets:
mAChR
Description:
Anisodamine is a alkaloid shown to be a weak antagonist of α1-adrenoceptors, blocking WB-4101 and clonidine by binding in brain membrane preparations.
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Purity:
≥98%
Appearance:
White to beige powder
Synonyms:
7-hydroxyhyoscyamine; 6-Hydroxy hyoscyamine; αS-(hydroxymethyl)-benzeneacetic acid, (1R,​3S,​5R,​6S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]​oct-3-yl ester;
Solubility:
Soluble in DMSO
Storage:
Store at -20 °C
MSDS:
Inquire
Application:
A weak antagonist of α1-adrenoceptors
Quality Standard:
Enterprise Standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity:
Milligrams-Grams
Boiling Point:
423.1ºC at 760 mmHg
Melting Point:
62-63 °C
Density:
1.27
InChIKey:
WTQYWNWRJNXDEG-VXUTWAGNSA-N
InChI:
1S/C17H23NO4/c1-18-12-7-13(9-15(18)16(20)8-12)22-17(21)14(10-19)11-5-3-2-4-6-11/h2-6,12-16,19-20H,7-10H2,1H3/t12-,13-,14?,15+,16-/m0/s1
Canonical SMILES:
CN1C2CC(CC1C(C2)O)OC(=O)C(CO)C3=CC=CC=C3
1.Study on the synthesis and biological activities of α-substituted arylacetates derivatives.
Liu J1, Chen C2, Wu F2, Tang J2. Bioorg Med Chem Lett. 2016 Apr 1;26(7):1715-9. doi: 10.1016/j.bmcl.2016.02.055. Epub 2016 Feb 22.
Anisodamine was isolated from the medicinal herb, it was used in the treatment of gastrointestinal smooth muscle spasm, infective toxic shock and organophosphorus intoxication. But there is no report about anisodamine with α-glucosidase inhibitory activity. In order to find novel α-glucosidase inhibitors, a series of α-substituted arylacetates derivatives have been synthesized based on the active unit of anisodamine. In α-glucosidase assay, compound 9 in Schiff base form and compound 22 in ester form show strong inhibition against α-glucosidase with IC50 value of 46.81μM and 83.76μM, respectively. Compounds 9 and 22 exhibit comparable good antidiabetic activities as commercial drug Glimepiride. In addition, Schiff bases of α-substituted arylacetates show antitumor activities against human cancer cell lines, where compound 9 with thiourea moiety performs the best antitumor activity. We anticipate that our research will provide potential candidate scaffolds for antidiabetic drug design.
2.Possible Role for Anisodamine in Organophosphate Poisoning.
Eisenkraft A1,2,3, Falk A1. Br J Pharmacol. 2016 Mar 24. doi: 10.1111/bph.13486. [Epub ahead of print]
In cases of organophosphate poisoning patients are treated with a combination of antidotes. Beside these poison-directed antidotes, supportive treatment like supplemental oxygen and ventilation, as well as other modalities may be needed due to the wide range of toxic effects. Anisodamine is a belladonna alkaloid, and like other drugs from this family is non subtype-selective muscarinic, and a nicotinic cholinergic antagonist, which has been employed in traditional Chinese medicine. As a muscarinic antagonist, it displays similar pharmacological effects as atropine and scopolamine. Anisodamine is less potent than atropine and scopolamine, but also less toxic. Current in vitro and animal model studies demonstrate protective effects of anisodamine in a variety of diseases. Organophosphate poisoning involves not only the central and peripheral nervous systems, but also the cardiac and respiratory systems, as well as activation of inflammatory processes and oxidative stress.
3.Effectiveness of anisodamine for the treatment of critically ill patients with septic shock (ACIdoSIS study): study protocol for randomized controlled trial.
Zhang Z1, Zhou J1, Shang Y1, Wang X1, Yin R1, Zhu Z1, Chen W1, Tian X1, Yu Y1, Zuo X1, Chen K1, Ji X1, Ni H1; Anisodamine Critically Ill SeptIc Shock (ACIdoSIS) study group. Ann Transl Med. 2015 Oct;3(17):246. doi: 10.3978/j.issn.2305-5839.2015.10.03.
BACKGROUND: Septic shock is an important contributor of mortality in the intensive care unit (ICU). Although strenuous effort has been made to improve its outcome, the mortality rate is only marginally decreased. The present study aimed to investigate the effectiveness of anisodamine in the treatment of septic shock, in the hope that the drug will provide alternatives to the treatment of septic shock.
4.Activation of α7 Nicotinic Acetylcholine Receptor Decreases On-site Mortality in Crush Syndrome through Insulin Signaling-Na/K-ATPase Pathway.
Fan BS1, Zhang EH2, Wu M1, Guo JM3, Su DF1, Liu X1, Yu JG1. Front Pharmacol. 2016 Mar 29;7:79. doi: 10.3389/fphar.2016.00079. eCollection 2016.
On-site mortality in crush syndrome remains high due to lack of effective drugs based on definite diagnosis. Anisodamine (Ani) is widely used in China for treatment of shock, and activation of α7 nicotinic acetylcholine receptor (α7nAChR) mediates such antishock effect. The present work was designed to test whether activation of α7nAChR with Ani decreased mortality in crush syndrome shortly after decompression. Sprague-Dawley rats and C57BL/6 mice with crush syndrome were injected with Ani (20 mg/kg and 28 mg/kg respectively, i.p.) 30 min before decompression. Survival time, serum potassium, insulin, and glucose levels were observed shortly after decompression. Involvement of α7nAChR was verified with methyllycaconitine (selective α7nAChR antagonist) and PNU282987 (selective α7nAChR agonist), or in α7nAChR knockout mice. Effect of Ani was also appraised in C2C12 myotubes. Ani reduced mortality and serum potassium and enhanced insulin sensitivity shortly after decompression in animals with crush syndrome, and PNU282987 exerted similar effects.
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CAS 55869-99-3 Anisodamine

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