Anabasine
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Basic Info
| Common Name | Anabasine(F04816) |
| 2D Structure | |
| Description | Anabasine is a nicotinic receptor agonist toxin and Cholinesterase inhibitor which acts upon the nicotinic acetylcholine receptors. Anabasine is an unstable yellow liquid which is succeptable to light, heat and moisture. It's decomposition products include Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases and carbon dioxide. Anabasine is a pyridine alkaloid found in the stem of the (Nicotiana glauca) plant, a close relative of (Nicotiana tabacum) the common tobacco plant. Anabasine is a metabolite of nicotine which can be used as an indicator of a person's exposure to tobbacco smoke. A piperidine botanical insecticide. |
| FRCD ID | F04816 |
| CAS Number | 13078-04-1 |
| PubChem CID | 2181 |
| Formula | C10H14N2 |
| IUPAC Name | 3-piperidin-2-ylpyridine |
| InChI Key | MTXSIJUGVMTTMU-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H14N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h3-4,6,8,10,12H,1-2,5,7H2 |
| Canonical SMILES | C1CCNC(C1)C2=CN=CC=C2 |
| Isomeric SMILES | C1CCNC(C1)C2=CN=CC=C2 |
| Wikipedia | Anabasine |
| Synonyms |
(+-)-Anabasine
3-(piperidin-2-yl)pyridine
13078-04-1
Anabasine
DL-Anabasine
Neonicotine
2-Pyridin-3-ylpiperidine
(+/-)-Anabasine
3-(2-Piperidinyl)pyridine
3-piperidin-2-ylpyridine
|
| Classifies |
Plant Toxin
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Alkaloids and derivatives |
| Class | Not available |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Alkaloids and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Alkaloid or derivatives - Aralkylamine - Pyridine - Piperidine - Heteroaromatic compound - Azacycle - Organoheterocyclic compound - Secondary amine - Secondary aliphatic amine - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Amine - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 162.236 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 1 |
| Complexity | 136 |
| Monoisotopic Mass | 162.116 |
| Exact Mass | 162.116 |
| XLogP | 1 |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9405 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.5109 |
| P-glycoprotein Substrate | Non-substrate | 0.5617 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9288 |
| Non-inhibitor | 0.9478 | |
| Renal Organic Cation Transporter | Inhibitor | 0.6128 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7005 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8412 |
| CYP450 2D6 Substrate | Non-substrate | 0.5352 |
| CYP450 3A4 Substrate | Non-substrate | 0.7496 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9107 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8751 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8931 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9026 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8310 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7871 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9436 |
| Inhibitor | 0.5000 | |
| AMES Toxicity | Non AMES toxic | 0.8464 |
| Carcinogens | Non-carcinogens | 0.9476 |
| Fish Toxicity | High FHMT | 0.7585 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9525 |
| Honey Bee Toxicity | Low HBT | 0.8133 |
| Biodegradation | Not ready biodegradable | 0.9791 |
| Acute Oral Toxicity | III | 0.4993 |
| Carcinogenicity (Three-class) | Non-required | 0.7954 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.3905 | LogS |
| Caco-2 Permeability | 1.1816 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.5447 | LD50, mol/kg |
| Fish Toxicity | 1.9502 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.8260 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Abuse potential of non-nicotine tobacco smoke components: acetaldehyde,nornicotine, cotinine, and anabasine. | Nicotine Tob Res | 2013 Mar | 22990226 |
| Piperidine, pyridine alkaloid inhibition of fetal movement in a day 40 pregnant goat model. | Food Chem Toxicol | 2013 Aug | 23603380 |
| Risk assessment for side-effects of neonicotinoids against bumblebees with and without impairing foraging behavior. | Ecotoxicology | 2010 Jan | 19757031 |
| Trifluoroacetyl neonicotinoid insecticides with enhanced hydrophobicity and effectiveness. | J Agric Food Chem | 2010 Apr 28 | 20369802 |
| Accidental fatal poisoning by Nicotiana glauca: identification of anabasine by high performance liquid chromatography/photodiode array/mass spectrometry. | Forensic Sci Int | 2002 Jul 17 | 12175951 |
| Fatal poisoning from Nicotiana glauca leaves: identification of anabasine by gas-chromatography/mass spectrometry. | J Forensic Sci | 2000 May | 10855991 |
| Optimization study for the reversed-phase ion-pair liquid chromatographic determination of nicotine in commercial tobacco products. | J Chromatogr A | 1999 Aug 13 | 10481983 |
| [Pharmacological agents in controlling smoking]. | Biull Vsesoiuznogo Kardiol Nauchn Tsentra AMN SSSR | 1987 | 3606829 |
Targets
- General Function:
- Ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA1
- Uniprot ID:
- P02708
- Molecular Weight:
- 54545.235 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNB1
- Uniprot ID:
- P11230
- Molecular Weight:
- 56697.9 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum
- General Function:
- Acetylcholine-activated cation-selective channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRND
- Uniprot ID:
- Q07001
- Molecular Weight:
- 58894.55 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum
- General Function:
- Cation transmembrane transporter activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNE
- Uniprot ID:
- Q04844
- Molecular Weight:
- 54696.54 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum
- General Function:
- Channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNG
- Uniprot ID:
- P07510
- Molecular Weight:
- 57882.8 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA3
- Uniprot ID:
- P32297
- Molecular Weight:
- 57479.54 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA5
- Uniprot ID:
- P30532
- Molecular Weight:
- 53053.965 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum
- General Function:
- Acetylcholine-activated cation-selective channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA6
- Uniprot ID:
- Q15825
- Molecular Weight:
- 56897.745 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodiun ions.
- Gene Name:
- CHRNB2
- Uniprot ID:
- P17787
- Molecular Weight:
- 57018.575 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum
- General Function:
- Drug binding
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNB3
- Uniprot ID:
- Q05901
- Molecular Weight:
- 52728.215 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNB4
- Uniprot ID:
- P30926
- Molecular Weight:
- 56378.985 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodium ions.
- Gene Name:
- CHRNA4
- Uniprot ID:
- P43681
- Molecular Weight:
- 69956.47 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Schmitt JD, Sharples CG, Caldwell WS: Molecular recognition in nicotinic acetylcholine receptors: the importance of pi-cation interactions. J Med Chem. 1999 Aug 12;42(16):3066-74. [10447950 ]
- General Function:
- Toxic substance binding
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is blocked by alpha-bungarotoxin.
- Gene Name:
- CHRNA7
- Uniprot ID:
- P36544
- Molecular Weight:
- 56448.925 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Schmitt JD, Sharples CG, Caldwell WS: Molecular recognition in nicotinic acetylcholine receptors: the importance of pi-cation interactions. J Med Chem. 1999 Aug 12;42(16):3066-74. [10447950 ]
- General Function:
- Receptor binding
- Specific Function:
- Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma.
- Gene Name:
- CHRNA10
- Uniprot ID:
- Q9GZZ6
- Molecular Weight:
- 49704.295 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum
- General Function:
- Drug binding
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA2
- Uniprot ID:
- Q15822
- Molecular Weight:
- 59764.82 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum
- General Function:
- Calcium channel activity
- Specific Function:
- Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding induces a conformation change that leads to the opening of an ion-conducting channel across the plasma membrane (PubMed:11752216, PubMed:25282151). The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane (PubMed:11752216, PubMed:25282151). In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma. May also regulate keratinocyte adhesion (PubMed:11021840).
- Gene Name:
- CHRNA9
- Uniprot ID:
- Q9UGM1
- Molecular Weight:
- 54806.63 Da
- Mechanism of Action:
- Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum