| Record Information |
|---|
| Version | 1.0 |
|---|
| Created at | 2006-08-13 17:16:37 UTC |
|---|
| Updated at | 2020-11-24 22:12:03 UTC |
|---|
| NP-MRD ID | NP0000006 |
|---|
| Secondary Accession Numbers | None |
|---|
| Natural Product Identification |
|---|
| Common Name | Anabasine |
|---|
| Description | Anabasine, also known as (+-)-anabasine or neonicotine, 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. Anabasine is a very strong basic compound (based on its pKa). Anabasine is a potentially toxic compound. A pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3. |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| (+-)-Anabasine | ChEBI | | Neonicotine | HMDB | | (+/-)-anabasine | HMDB | | (-)-2-(3'-Pyridyl)piperidine | HMDB | | (-)-Anabasine | HMDB | | (S)-3-(2-Piperidinyl)pyridine | HMDB | | 2-(3'-Pyridyl) piperidine | HMDB | | 2-(3-Pyridinyl)piperidine | HMDB | | 3-(2-Piperidinyl)pyridine | HMDB | | Anabasin | HMDB | | Anabazin | HMDB | | DL-Anabasine | HMDB | | L-3-(2'-Piperidyl)pyridine | HMDB | | Neonikotin | HMDB | | S-(-)-Anabasine | HMDB |
|
|---|
| Chemical Formula | C10H14N2 |
|---|
| Average Molecular Weight | 162.2316 |
|---|
| Monoisotopic Molecular Weight | 162.115698458 |
|---|
| IUPAC Name | 3-(piperidin-2-yl)pyridine |
|---|
| Traditional Name | anabasine |
|---|
| CAS Registry Number | 13078-04-1 |
|---|
| SMILES | C1CCC(NC1)C1=CN=CC=C1 |
|---|
| InChI Identifier | 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 |
|---|
| InChI Key | MTXSIJUGVMTTMU-UHFFFAOYSA-N |
|---|
| Spectra |
|---|
|
| | | Species of Origin |
|---|
| Species | Animalia; Plantae |
|---|
| Chemical Taxonomy |
|---|
| Description | 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Alkaloids and derivatives |
|---|
| Class | Not Available |
|---|
| Sub Class | Not Available |
|---|
| Direct Parent | Alkaloids and derivatives |
|---|
| Alternative Parents | |
|---|
| 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
|
|---|
| Molecular Framework | Aromatic heteromonocyclic compounds |
|---|
| External Descriptors | |
|---|
| Physical Properties |
|---|
| State | Liquid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | 9 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 1000 mg/mL at 25 °C | Not Available | | LogP | 0.97 | HANSCH,C ET AL. (1995) |
|
|---|
| Predicted Properties | |
|---|
| General References | - Moyer TP, Charlson JR, Enger RJ, Dale LC, Ebbert JO, Schroeder DR, Hurt RD: Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles. Clin Chem. 2002 Sep;48(9):1460-71. [PubMed:12194923 ]
- Xu X, Iba MM, Weisel CP: Simultaneous and sensitive measurement of anabasine, nicotine, and nicotine metabolites in human urine by liquid chromatography-tandem mass spectrometry. Clin Chem. 2004 Dec;50(12):2323-30. Epub 2004 Oct 7. [PubMed:15472033 ]
- Mizrachi N, Levy S, Goren ZQ: Fatal poisoning from Nicotiana glauca leaves: identification of anabasine by gas-chromatography/mass spectrometry. J Forensic Sci. 2000 May;45(3):736-41. [PubMed:10855991 ]
|
|---|
