Anisodamine is a ntural product extracted from Chinese solanacea plant, acting as a weak inhibitor/antagonist of alpha-1 adrenergic receptors and mAChRs.
Physicochemical Properties
| Molecular Formula | C17H23NO4 |
| Molecular Weight | 305.36882 |
| Exact Mass | 305.163 |
| Elemental Analysis | C, 66.86; H, 7.59; N, 4.59; O, 20.96 |
| CAS # | 55869-99-3 |
| Related CAS # | Anisodamine hydrobromide; 55449-49-5; Anisodamine hydrochloride; 131674-05-0 |
| PubChem CID | 6918612 |
| Appearance | White to off-white solid powder |
| Density | 1.27 |
| Boiling Point | 423.1ºC at 760 mmHg |
| Index of Refraction | 1.565 |
| LogP | 0.839 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 22 |
| Complexity | 396 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | CN1[C@H]2[C@@H](O)C[C@@H]1C[C@H](OC([C@@H](C3=CC=CC=C3)CO)=O)C2 |
| InChi Key | WTQYWNWRJNXDEG-RBZJEDDUSA-N |
| InChi Code | 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 |
| Chemical Name | [(1R,3S,5R,6S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenylpropanoate |
| Synonyms | 6-Hydroxy hyoscyamine; 654 II; 654-II; 654II |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Nicotinic cholinoceptor |
| ln Vitro |
Anisodamine pretreatment (100 μg/mL; 20 minutes; RAW264.7 cells) significantly attenuates the average fluorescence intensity of α-bungarotoxin binding compared to Ach alone[2]. Anisodamine may act by blocking muscarinic receptors, which in turn increases the amount of endogenous ACh that binds to the α-7nAChR[2]. |
| ln Vivo | Anisodamine (50 mg/kg; intraperitoneally; 72 hours) significantly lowers mortality to 20%[2]. |
| Animal Protocol |
LPS-Induced Shock Mice 50 mg/kg I.p. |
| References |
[1]. Possible role for anisodamine in organophosphate poisoning. Br J Pharmacol. 2016 Jun;173(11):1719-27. [2]. Antishock effect of anisodamine involves a novel pathway for activating alpha7 nicotinic acetylcholine receptor. Crit Care Med. 2009;37(2):634-641. |
| Additional Infomation |
Anisodamine has been investigated for the treatment of Intestinal Diseases. 6-Hydroxyhyoscyamine has been reported in Duboisia myoporoides, Hyoscyamus albus, and Anisodus tanguticus with data available. See also: 6-Hydroxyhyoscyamine (annotation moved to). |
Solubility Data
| Solubility (In Vitro) |
DMSO: ≥ 100 mg/mL (~327.5 mM) H2O: ~20 mg/mL (~65.5 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.19 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.19 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (8.19 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 50 mg/mL (163.74 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2747 mL | 16.3736 mL | 32.7472 mL | |
| 5 mM | 0.6549 mL | 3.2747 mL | 6.5494 mL | |
| 10 mM | 0.3275 mL | 1.6374 mL | 3.2747 mL |