Anabasine is a pyridine and piperidine alkaloid found in the Tree Tobacco (Nicotiana glauca Nicotiana tabacum nicotine . Its principal (historical) industrial use is as an insecticide .
Anabasine is present in trace amounts in tobacco smoke, and can be used as an indicator of a person's exposure to tobacco smoke.[1]
Pharmacology [ edit ] 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 .[2] teratogenic in swine.[3]
The intravenous LD50 of anabasine ranges from 11 mg/kg to 16 mg/kg in mice , depending on the enantiomer .[4]
Analogs [ edit ] B. Bhatti, et al. made some higher potency sterically strained bicyclic analogs of anabasine:[5]
2-(Pyridin-3-yl)-1-azabicyclo[3.2.2]nonane,
2-(Pyridin-3-yl)-1-azabicyclo[2.2.2]octane,
and 2-(Pyridin-3-yl)-1-azabicyclo[3.2.1]octane.
References [ edit ]
^ Jacob, P. 3rd.; Yu, L.; Shulgin, A. T.; Benowitz, N. L. (1999). "Minor Tobacco Alkaloids as Biomarkers for Tobacco Use: Comparison of Users of Cigarettes, Smokeless Tobacco, Cigars, and Pipes" . Am J Public Health . 89 (5): 731–6. doi :10.2105/AJPH.89.5.731 . PMC 1508721 PMID 10224986 . ^ Mizrachi, N.; Levy, S.; Goren, Z. Q. (2000). "Fatal Poisoning from Nicotiana glauca Leaves: Identification of Anabasine by Gas-Chromatography / Mass Spectrometry". Journal of Forensic Sciences . 45 (3): 736–41. PMID 10855991 . ^ "Notes on Poisoning: Nicotiana tabacum " . Canadian Biodiversity Information Facility. 2008-03-18. Retrieved 2008-05-01 . ^ Lee, S. T.; Wildeboer, K.; Panter, K. E.; Kem, W. R.; Gardner, D. R.; Molyneux, R. J.; Chang, C. W.; Soti, F.; Pfister, J. A. (2006). "Relative Toxicities and Neuromuscular Nicotinic Receptor Agonistic Potencies of Anabasine Enantiomers and Anabaseine". Neurotoxicology and Teratology . 28 (2): 220–8. doi :10.1016/j.ntt.2005.12.010 . PMID 16488116 . ^ Bhatti, B.; Strachan, J.; Breining, S.; Miller, C.; Tahiri, P.; Crooks, P.; Deo, N.; Day, C.; Caldwell, W. (2008). "Synthesis of 2-(Pyridin-3-yl)-1-azabicyclo[3.2.2]nonane, 2-(Pyridin-3-yl)-1-azabicyclo[2.2.2]octane, and 2-(Pyridin-3-yl)-1-azabicyclo[3.2.1]octane, a Class of Potent Nicotinic Acetylcholine Receptor-Ligands". The Journal of Organic Chemistry . 73 (9): 3497–507. doi :10.1021/jo800028q . PMID 18363376 .
Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
Cholinergics
Convulsants
Eugeroics
Oxazolines
Phenethylamines
1-(4-Methylphenyl)-2-aminobutane 1-Phenyl-2-(piperidin-1-yl)pentan-3-one 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fuoroamphetamine 2-Fuoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2-Phenyl-3-methylaminobutane 2,3-MDA 3-Fuoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-CMC 4-Ethylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-Methylbuphedrone 4-Methylcathinone 4-MMA 4-Methylpentedrone 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine , Levoamphetamine )Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzedrone Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Buphedrone Bupropion Butylone Camfetamine Cathine Cathinone Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D -DeprenylDenopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA (Dextrodopa , Levodopa )Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylnorepinephrine Ethylone Etilamfetamine Etilefrine Famprofazone Fencamfamine Fencamine Fenethylline Fenfluramine (Dexfenfluramine , Levofenfluramine )Fenproporex Feprosidnine Flephedrone Fludorex Formetorex Furfenorex Gepefrine Hexapradol Hexedrone HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine IMP Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L -DeprenylLefetamine Lisdexamfetamine Lophophine MBDB MDA MDBU MDEA MDMA MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine , Levomethamphetamine )Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylenedioxycathinone Methylone Mexedrone MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N-Benzyl-1-phenethylamine N-Ethylbuphedrone N-Ethylhexedrone N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L -NorpseudoephedrineOctopamine (drug) Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Pentedrone Pentylone Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Phthalimidopropiophenone Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol (Levosalbutamol )Sibutramine Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine
Phenylmorpholines
Piperazines
Piperidines
Pyrrolidines
Racetams
Tropanes
Tryptamines
Others
mACh
Antagonists: 3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g., brompheniramine , chlorphenamine , cyproheptadine , dimenhydrinate , diphenhydramine , doxylamine , mepyramine (pyrilamine) , phenindamine , pheniramine , promethazine , tripelennamine , triprolidine )Atropine Atropine methonitrate Atypical antipsychotics (e.g., clozapine , olanzapine , quetiapine , zotepine )Benactyzine Benzatropine (benztropine) Benzilylcholine mustard Benzydamine BIBN 99 Biperiden Bornaprine CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Caramiphen Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Dimethindene Dexetimide DIBD Dicyclomine (dicycloverine) Ditran EA-3167 EA-3443 EA-3580 EA-3834 Etanautine Etybenzatropine (ethybenztropine) Flavoxate Himbacine HL-031,120 Ipratropium bromide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Methoctramine Metixene N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Orphenadrine Otenzepad Oxybutynin PBID PD-102,807 PD-0298029 Phenglutarimide Phenyltoloxamine Pipenzolate bromide Pirenzepine Piroheptine Procyclidine Profenamine Revefenacin RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (hyoscine) Sofpironium bromide Solifenacin Telenzepine Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin , mirtazapine )Timepidium bromide Tiotropium bromide Tolterodine Tricyclic antidepressants (e.g., amitriptyline , butriptyline , clomipramine , desipramine , dosulepin (dothiepin) , doxepin , imipramine , lofepramine , nortriptyline , protriptyline , trimipramine )Trihexyphenidyl Tripitamine Tropacine Tropatepine Tropicamide Typical antipsychotics (e.g., chlorpromazine , loxapine , thioridazine )WIN-2299 Xanomeline Zamifenacin
nACh
Agonists: 5-HIAA A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine Anatoxin-a AR-R17779 Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Ivermectin Levamisole Lobeline MEM-63,908 (RG-3487) Morantel Nicotine (tobacco )NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Rivanicline RJR-2429 Sazetidine A SB-206553 Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberyldicholine Suxamethonium (succinylcholine) TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tropisetron UB-165 Varenicline WAY-317,538 XY-4083
. PMID 10224986. 
