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Submit Review(-)-Nicotine ditartrate
Description: Prototypical nAChR agonist
Chemical Name: (S)-(-)-1-Methyl-2-(3-pyridyl)pyrrolidine (+)-ditartrate salt
Purity: ≥99% (HPLC)
Biological Activity for (-)-Nicotine ditartrate
(-)-Nicotine ditartrate is a nicotinic acetylcholine receptor (nAChR) agonist (Ki values are 1, > 1000, 4000 and 7130 nM at α4β2, α1β1δγ, rat α7 and human α7 respectively). Exhibits vasoconstrictive, hypertensive and prothrombotic activity in vivo.
Technical Data for (-)-Nicotine ditartrate
| M. Wt | 462.41 |
| Formula | C10H14N2.2C4H6O6 |
| Storage | Desiccate at RT |
| Purity | ≥99% (HPLC) |
| CAS Number | 65-31-6 |
| PubChem ID | 11957628 |
| InChI Key | RFEJUZJILGIRHQ-OMDKHLBYSA-N |
| Smiles | CN(CCC2)[C@@H]2[C@]1=CC=CN=C1.OC([C@H](O)[C@@H](O)C(O)=O)=O.OC([C@H](O)[C@@H](O)C(O)=O)=O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for (-)-Nicotine ditartrate
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 46.24 | 100 | |
| DMSO | 34.68 | 75 |
Preparing Stock Solutions for (-)-Nicotine ditartrate
The following data is based on the product molecular weight 462.41. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.16 mL | 10.81 mL | 21.63 mL |
| 5 mM | 0.43 mL | 2.16 mL | 4.33 mL |
| 10 mM | 0.22 mL | 1.08 mL | 2.16 mL |
| 50 mM | 0.04 mL | 0.22 mL | 0.43 mL |
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Product Datasheets for (-)-Nicotine ditartrate
References for (-)-Nicotine ditartrate
References are publications that support the biological activity of the product.
Donnelly-Roberts et al (1998) ABT-594 [(R)-5-(2-azetidinylmethoxy)-2-chloropyridine]: A novel, orally effective analgesic acting via neuronal nicotinic acetylcholine receptors: I In vitro characterization. J.Pharmacol.Exp.Ther. 285 777 PMID: 9580626
Xiao et al (1998) Rat α3/β4 subtype of neuronal nicotinic acetylcholine receptor stably expressed in a transfected cell line: Pharmacology of ligand binding and function. Mol.Pharmacol. 54 322 PMID: 9687574
Mayhan (1999) Acute infusion of nicotine potentiates NE-induced vasoconstriction in the hamster cheek pouch. J.Lab.Clin.Med. 133 48 PMID: 10385481
If you know of a relevant reference for (-)-Nicotine ditartrate, please let us know.
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Keywords: (-)-Nicotine ditartrate, (-)-Nicotine ditartrate supplier, α4β2, agonists, a4b2, alpha4beta2, Nicotinic, Receptors, Acetylcholine, nAChR, (a4b2), (Non-selective), 3546, Tocris Bioscience
⚠ WARNING: This product can expose you to chemicals including Nicotine, which is known to the State of California to cause reproductive toxicity with developmental effects. For more information, go to www.P65Warnings.ca.gov
12 Citations for (-)-Nicotine ditartrate
Citations are publications that use Tocris products. Selected citations for (-)-Nicotine ditartrate include:
Lena et al (2020) A molecular filter for the cnidarian stinging response. Elife 9 PMID: 32452384
David S et al (2020) NACHO Engages N-Glycosylation ER Chaperone Pathways for α7 Nicotinic Receptor Assembly. Cell Rep 32 108025 PMID: 32783947
Tang et al (2015) Identification and in vitro pharmacological characterization of a novel and selective α7 nicotinic acetylcholine receptor agonist, Br-IQ17B. Iran Biomed J 36 800 PMID: 25948478
Chalabi-Yani et al (2015) Effect of Transient Inactivation of Ventral Tegmental Area on the Expression and Acquisition of Nicotine-Induced Conditioned Place Preference in Rats. Elife 19 214 PMID: 26210948
Miguel Angel Garcia-Bereguiain et al (2016) Spontaneous Release Regulates Synaptic Scaling in the Embryonic Spinal Network In Vivo The Journal of Neuroscience 6 7268 PMID: 27383600
Dorst et al (2020) Polysynaptic inhibition between striatal cholinergic interneurons shapes their network activity patterns in a dopamine-dependent manner. Nat Commun 11 5113 PMID: 33037215
Gu et al (2019) α6-Containing Nicotinic Acetylcholine Receptor Reconstitution Involves Mechanistically Distinct Accessory Components. Cell Rep 26 866 PMID: 30673609
Leão et al (2012) OLM interneurons differentially modulate CA3 and entorhinal inputs to hippocampal CA1 neurons. Nat Neurosci 15 1524 PMID: 23042082
Owaisat et al (2012) In vivo comparison of harmine efficacy against psychostimulants: preferential inhibition of the cocaine response through a glutamatergic mechanism. Neurosci Lett 525 12 PMID: 22877698
Marzena et al (2021) Chronic Lorcaserin Treatment Reverses the Nicotine Withdrawal-Induced Disruptions to Behavior and Maturation in Developing Neurons in the Hippocampus of Rats. Int J Mol Sci 22 PMID: 33467149
Jean-Marie et al (2022) β2* nicotinic acetylcholine receptor subtypes mediate nicotine-induced enhancement of Pavlovian conditioned responding to an alcohol cue. Front Behav Neurosci 16 1004368 PMID: 36311864
Asami et al (2019) Cholinergic Interneurons Amplify Thalamostriatal Excitation of Striatal Indirect Pathway Neurons in Parkinson's Disease Models. Neuron 101 444-458.e6 PMID: 30658860
Do you know of a great paper that uses (-)-Nicotine ditartrate from Tocris? Please let us know.
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Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
*Please note that Tocris will only send literature to established scientific business / institute addresses.
Nicotinic ACh Receptors Scientific Review
Updated in 2014, this review by Sue Wonnacott summarizes the diverse structure and function of nicotinic acetylcholine receptors and gives an in-depth review of the ligands available for nAChR research. Compounds available from Tocris are listed.