Anabasine

Manufactured by Merck Group

Sourced in United States

Anabasine is a laboratory equipment product manufactured by Merck Group. It is a chemical compound used in various research and analytical applications. The core function of Anabasine is to serve as a standard reference material and analytical reagent for scientific investigations.

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Lab products found in correlation

Nornicotine, by Merck Group (7 mentions) Cotinine, by Merck Group (5 mentions) Myosmine, by Merck Group (4 mentions) Anatabine, by Cayman Chemical (4 mentions) Formic acid, by Thermo Fisher Scientific (3 mentions) Anatabine, by LGC (2 mentions) Nicotine bitartrate, by Merck Group (2 mentions) Ammonium acetate, by Merck Group (2 mentions) Nicotine, by Merck Group (2 mentions) Nicotine n oxide, by Cayman Chemical (2 mentions) Nicotinamide, by Merck Group (2 mentions) Dizocilpine, by Merck Group (1 mentions) Anatabine, by Merck Group (1 mentions) Sib 1508y maleate, by Bio-Techne (1 mentions) S anabasine, by LGC (1 mentions) S 1 methylnicotinium iodide, by LGC (1 mentions) Harmane, by Merck Group (1 mentions) Norharmane, by Merck Group (1 mentions) Nicotine hydrogen tartrate, by Merck Group (1 mentions) Tyramine hcl, by Merck Group (1 mentions)

12 protocols using anabasine

Anabasine Treatment for Crithidia Infection

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Anabasine treatments commenced immediately post-inoculation and were provided throughout the 7 d experiment. Sucrose solutions with anabasine (5 ppm) were made by dissolving the liquid compound (+/- anabasine, 97% purity, Sigma-Aldrich, St. Louis, MO, USA; mixed enantiomers were also used in previous studies of Crithidia [16 (link),18 (link)]) in 30% w/w sucrose. Solutions were stored at 4°C and remade every 2 weeks. (Stock solutions of nicotine and related alkaloids are stable for >3 months at 4°C [68 ].) Bees were supplied with 500 μL treatment solution and fresh pollen (~50 mg) daily.
Bees were dissected 7 d post-infection to assess infection intensity using the methods described above (see Experimental Inoculations). Crithidia infection normally reaches a maximum by this time [67 (link)].

Palmer-Young E.C., Hogeboom A., Kaye A.J., Donnelly D., Andicoechea J., Connon S.J., Weston I., Skyrm K., Irwin R.E, & Adler L.S. (2017). Context-dependent medicinal effects of anabasine and infection-dependent toxicity in bumble bees. PLoS ONE, 12(8), e0183729.

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Acute Effects of Neuroactive Alkaloids

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Solutions of anabasine, anatabine and dizocilpine (Sigma, St. Louis, MO, USA) were prepared in pyrogen-free glassware in sterilized isotonic saline. All drug doses were given as the salt weight. Acute subcutaneous (SC) injections of anabasine, anatabine, dizocilpine or placebo were given in a volume of 1 ml/kg 20 minutes before the beginning of the test session. Drug treatments were given following a repeated measures counterbalanced design with at least two days between treatments.

Levin E.D., Hao I., Burke D., Cauley M., Hall B.J, & Rezvani A.H. (2014). Effects of Tobacco Smoke Constituents, Anabasine and Anatabine, on Memory and Attention in Female Rats. Journal of psychopharmacology (Oxford, England), 28(10), 915-922.

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Nicotinic Receptor Ligands: Acquisition and Characterization

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ACh, (−)-nicotine hydrogen tartrate salt ((S)-nicotine), anabasine ((S, R)-anabasine), (±)-nornicotine (nornicotine), 5-(1-methyl-pyrrolidin-2-yl)-pyridin-2-ylamine dihydrochloride (6-AN) and (−)-cotinine ((S)-cotinine) were purchased from Sigma-Aldrich (St Louis, MO, USA). SIB 1508Y maleate ((S)—SIB 1508Y) was obtained from Tocris Bioscience (Ellisville, MO, USA). (S)-anabasine, rac-5-methylnicotine (5-methylnicotine), S-(−)-nicotine-5-carboxaldehyde ((S)-nicotine-5-carboxaldehyde), (±)-6-methylnicotine (6-methylnicotine), (S)-1-methylnicotinium iodide ((S)-1-methylnicotinium), (S)-1’-methylnicotinium iodide ((S)-1’-methylnicotinium), (R, S)—N-ethyl nornicotine (homonicotine), N-methyl anabasine were purchased from Toronto Research Chemicals (Toronto, ON, Canada).

Zheng F., Du X., Chou T.H., Robertson A.P., Yu E.W., VanVeller B, & Martin R.J. (2016). (S)-5-ethynyl-anabasine, a novel compound, is a more potent agonist than other nicotine alkaloids on the nematode Asu-ACR-16 receptor. International Journal for Parasitology: Drugs and Drug Resistance, 7(1), 12-22.

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Nicotinic Alkaloid Administration Protocol

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(−)-Nicotine bitartrate, (+/−) nornicotine, (+/−) anabasine, (+/−) myosmine, and (−)-cotinine were obtained from Sigma (St Louis, MO). (+/−) Anatabine was obtained from Toronto Research Chemicals, Inc. (Ontario, Canada). All drugs were prepared in sterile saline, adjusted to a pH of 7.4 using dilute NaOH, and administered s.c. in a volume of 1 ml/kg. All drug doses are expressed as the base.

Harris A.C., Tally L., Muelken P., Banal A., Schmidt C.E., Cao Q, & LeSage M.G. (2015). Effects of nicotine and minor tobacco alkaloids on intracranial-self-stimulation in rats. Drug and alcohol dependence, 153, 330-334.

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Tobacco Constituents Bioavailability Protocol

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Nicotine hydrogen tartrate, tyramine HCl, anabasine, myosmine, harmane, and norharmane were purchased from Sigma-Aldrich (St. Louis, MO, USA). D, L Nornicotine was purchased from Matrix Scientific (Columbia, SC, USA), and D,L anatabine was purchased from Fisher Scientific (Pittsburgh, PA, USA). Nicotine, nornicotine, tyramine HCl, myosmine, anabasine and anatabine were dissolved in 0.9% sterile saline (Hospira Inc, Lake Forest, IL, USA). harmane and norharmane were both dissolved in a solution containing equal parts sterile saline and DMSO (Sigma-Aldrich), which also served as the vehicle for these two compounds. All tobacco constituent solutions were injected (s.c.) in a volume of 1.0 ml/kg body weight.

Hall B.J., Wells C., Allenby C., Lin M.Y., Hao I., Marshall L., Rose J.E, & Levin E.D. (2014). Differential Effects of Non-Nicotine Tobacco Constituent Compounds on Nicotine Self-Administration in Rats. Pharmacology, biochemistry, and behavior, 120, 103-108.

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Radioligand Binding Assay for Nicotinic Receptors

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D-MEM and Penicillin/streptomycin were purchased from Quality Biologicals
(Gaithersburg, MD). Fetal Bovine serum was obtained from Atlanta Biologicals
(Lawrenceville, Ga). [³H]-Epibatidine (>97
%) was purchased from Perkin Elmer (Waltham, MA). IAM (immobilized
artificial membrane) particles were purchased from Regis Technologies Inc
(Morton Grove, IL). Hygromycin (80%) was obtained from Amresco (Solon,
OH). The HR 5/2 glass columns were purchased from Amersham Pharmacia Biotech
(Uppsala, Sweden). Tris-HCl and NaCl (>99 %) were obtained from
Fischer Scientific (Jessup, MD). MgCl₂ (≥ 98%),,
CaCl₂ (≥ 99%), KCl (>99 %), Sodium
cholate hydrate (>99 %),, Leupeptin (> 90%), Ammonium
acetate (>99 %), Benzamidine hydrochloride (>99 %),
Phenylmethanesulfonyl fluoride (PMSF, ≥98.5%), G418, Nicotine
(> 99%), Cytisine (≥ 99%), NorNicotine (≥
98%), Anabasine (≥ 97%), Mecamylamine hydrochloride
(> 96%), Bupropion hydrochloride (≥ 98%), and all
other chemicals were purchased from Sigma-Aldrich unless otherwise stated (St.
Louis, MO). Club Moss (Lycopodium clavatum L).
aqueous-alcoholic extract was from Hawaii Pharm (Honolulu, Hawaii) and
Trigonella foenum-graecum L. aqueous-alcoholic extracts
wasfrom Herb Pharm (Williams, OR).

Ciesla L., Okine M., Rosenberg A., Dossou K.S., Toll L., Wainer I.W, & Moaddel R. (2015). Development and characterization of the α3β4α5 nicotinic receptor cellular membrane affinity chromatography column and its application for on line screening of plant extracts. Journal of chromatography. A, 1431, 138-144.

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Subcutaneous Administration of Nicotinic Compounds

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The compounds (−)-nicotine bitartrate, (+/−)nornicotine, and (+/−)anabasine were obtained from Sigma Chemical Co. (St. Louis, MO, USA). The compound (+/−)anatabine was obtained from Toronto Research Chemicals, Inc. (North York, ON, Canada). All drugs were dissolved into sterile saline. The pH of all solutions was adjusted to 7.4 using dilute NaOH or HCl. All drugs were administered subcutaneously (sc) in a volume of 1 mL/kg. All drug doses are expressed as the base. The dose of each drug was as follows, nicotine: 0.50 mg/kg; nornicotine: 6.00 mg/kg; anatabine 3.00 mg/kg; anabasine 3.00 mg/kg. The doses selected were based on those used in our previous study evaluating the effects of the MTAs on deprivation-induced food intake [44 (link)]. The range of doses used in the previous investigation was narrowed down in the present study to a single dose of each drug that had previously produced reductions in food intake, without significant compensatory increases in food intake later in the day.

Grebenstein P.E., Erickson P., Grace M, & Kotz C.M. (2022). Anatabine, Nornicotine, and Anabasine Reduce Weight Gain and Body Fat through Decreases in Food Intake and Increases in Physical Activity. Journal of Clinical Medicine, 11(3), 481.

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Alkaloids Extraction and HPLC Analysis

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The solvents used for alkaloids extraction and HPLC analysis were methanol and acetonitrile, from Merck (Darmstadt, Germany), and a 15 mM ammonium formate buffer prepared using ammonium formate from Sigma-Aldrich (St. Louis, MO). The water was deionised and filtered using a Milli-Q system (Millipore, Billerica, MA). Hydrochloric acid and sodium hydroxide used for adjusting pH were from Merck (Darmstadt, Germany). The analytical standards used were nornicotine, myosmine and cotinine from Sigma, nicotine from Fluka (Milwaukee, WI), anabasine from Sigma-Aldrich, anatabine from Cayman Chemical Company (AnnArbor, MI), and the internal standards used were caffeine from Ajax Finechem (Sydney, Australia).

Moghbel N., Ryu B., Ratsch A, & Steadman K.J. (2017). Nicotine alkaloid levels, and nicotine to nornicotine conversion, in Australian Nicotiana species used as chewing tobacco. Heliyon, 3(11), e00469.

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Characterization of Nicotine Metabolites

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Chemicals, biochemicals and buffers were purchased from Sigma-Aldrich Chemical Co. and Thermo Fisher Scientific. Anatabine (2), nicotyrine, and nicotine-N-oxide were purchased from Cayman Chemical. R-nicotine and 6-hydroxy-L-nicotine (11) were purchased from Toronto Research Chemicals. All other commercially available compounds were purchased from Sigma-Aldrich, including nornicotine (1), cotinine, acetyl choline, nicotinamide, choline, glutamate, nicotinamide adenine dinucleotide (NAD), varenicline, cytosine, γ-aminobutyric acid (GABA), mecamylamine, dopamine, serotonin, anabasine (4), and myosmine. Syntheses of 3, 5, 6, 8, 9, 10, and 12 are detailed in the Supporting Information. S-nicotine purchased from Sigma-Aldrich is sold as ≥99% pure. Upon further analysis by LC-MS, this stock solution was found to be contaminated with ~5% nicotyrine.

Tararina M.A., Xue S., Smith L.C., Muellers S.N., Miranda P.O., Janda K.D, & Allen K.N. (2018). Crystallography Coupled with Kinetic Analysis Provide Mechanistic Underpinnings of a Nicotine-Degrading Enzyme. Biochemistry, 57(26), 3741-3751.

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Quantification of Tobacco Alkaloids and Metabolites

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Nicotine, anabasine, myosmine, nicotinamide, cotinine, norNicotine, norcotinine, nicotinic acid, and their corresponding deuterated or ¹³C internal standards were purchased from Sigma-Aldrich (St. Louis, MO, USA) unless otherwise stated below. Anatabine was purchased from Cayman Chemicals (Ann Arbor, MI, USA), and Anatabine-d4 and myosmine-d4 were obtained from Toronto Research Chemicals (Ontario, ON, Canada). Solvents used for LC-MS analysis were from Honeywell (Charlotte, NC, USA). Ammonium acetate was from Sigma-Aldrich, and formic acid was from Thermo Fisher Scientific (Waltham, MA, USA).
The following solvents used for microfractionation were purchased from Shanghai Titan Scientific Co. Ltd. (Shanghai, China): butanol (≥99.5%, certified analytical reagent (AR)), dichloromethane (≥99.5%, AR), ethyl acetate (≥99.5%, AR), 95% ethanol (95%, AR), ethanol (≥99.7%, AR), hexane (≥97.0%, AR), and methanol (≥99.5%, AR). Ultrapure water was produced by Bicoll (Planegg, Germany). The pipettes for 96-well microtiter plates were produced by Eppendorf (Hamburg, Germany). Polytetrafuoroethylene membrane filters (0.22 µm) and syringes were purchased from Anpel technologies (Shanghai, China).

Laszlo C., Kaminski K., Guan H., Fatarova M., Wei J., Bergounioux A., Schlage W.K., Schorderet-Weber S., Guy P.A., Ivanov N.V., Lamottke K, & Hoeng J. (2022). Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species. Molecules, 27(22), 8105.

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