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Anabasine

Cat No.:V11279 Purity: ≥98%
Anabasine ((S)-Anabasine) is an alkaloid, a component of tobacco.
Anabasine
Anabasine Chemical Structure CAS No.: 494-52-0
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
50mg
100mg
250mg
500mg
Other Sizes

Other Forms of Anabasine:

  • (±) Anabasine
  • Anabasine hydrochloride ((+)-Anabasine hydrochloride; (S)-Anabasine hydrochloride; (+)-Anabasine hydrochloride)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Anabasine ((S)-Anabasine) is an alkaloid, a component of tobacco. Anabasine is a botanical insecticide that works as a full agonist of nicotinic acetylcholine receptors (nAChRs). Anabasine induces depolarization in TE671 cells endogenously expressing human myotype nAChRs (EC50=0.7 µM).
Biological Activity I Assay Protocols (From Reference)
ln Vivo
Anabasine effectively restored damage at doses of 0.2 mg/kg (p<0.05) and 2 mg/kg (p<0.025). When taken alone, nectarine did not have any meaningful influence on response latency. In fact, the 0.06 mg/kg neocostalis dose significantly (p<0.05) aggravated dezocycline-induced impairment. None of these neophylline doses per se changed the accuracy of the selection. Individual dose comparisons showed that the 0.06 mg/kg dose of chrysanthine with dizozepine (6.7±2.6) resulted in a significant increase of non-responsive trials (p<0.05) compared to dizozepine alone (2.1±0.8) [1].
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Anabasine is readily absorbed from the skin and from mucous membranes.
Metabolism / Metabolites
IN VITRO METABOLISM OF (-)-METHYLANABASINE BY RAT, RABBIT & GUINEA PIG GAVE (-)-ANABASINE WHICH WAS METABOLIZED TO 1'-N-HYDROXYANABASINE & ANABASINE 1'DELTA-NITRONE. METABOLIC PRODUCTS OF FORTIFIED LUNG MICROSOMAL FRACTIONS WERE SIMILAR.
Toxicity/Toxicokinetics
Interactions
ANABASINE ENHANCED SEDATIVE ACTION OF RESERPINE, APOMORPHINE, & 5-HYDROXYTRYPTOPHAN IN FROGS & INHIBITED SEROTONIN UPTAKE BY HUMAN THROMBOCYTES.
References

[1]. Effects of tobacco smoke constituents, anabasine and anatabine, on memory and attention in female rats. J Psychopharmacol. 2014 Oct;28(10):915-22.

[2]. Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors. Neurotoxicol Teratol. May-Jun 2010;32(3):383-90.

Additional Infomation
(S)-anabasine is the (S)-enantiomer of anabasine.
(-)-Anabasine has been reported in Nicotiana suaveolens, Verbascum songaricum, and other organisms with data available.
Anabasine is a nicotine analog that is an alkaloid found in tree tobacco (Nicotiana glauca) and is comprised of a pyridine substituted by a piperidin-2-yl group at position 3. Anabasine has been used as an industrial insecticide and, since it is present in trace amounts in tobacco smoke, its detection in urine can be used as an indicator of exposure to tobacco smoke.
A piperidine botanical insecticide.
See also: Tobacco Leaf (part of).
Mechanism of Action
...ANABASINE AFFECT/S/ THE GANGLION OF THE INSECT CENTRAL NERVOUS SYSTEM, FACILITATING TRANS-SYNAPTIC CONDUCTION AT LOW CONCENTRATIONS AND BLOCKING CONDUCTION AT HIGHER LEVELS.
ANABASINE EXERTED NEUROMUSCULAR BLOCKING EFFECT ON ISOLATED RAT PHRENIC NERVE-DIAPHRAGM WHICH COULD BE PARTIALLY ANTAGONIZED BY NEOSTIGMINE. IT IS A DEPOLARIZING MUSCLE RELAXANT WITH SOME CHARACTERISTICS OF COMPETITIVE MUSCLE RELAXANTS.
Therapeutic Uses
EXPTL USE: ANABASINE (2 MG/KG/DAY, IP FOR 10 DAYS) INHIBITED THE INHIBITORY EFFECT OF CONCOMITANTLY ADMIN HYDROCORTISONE ON ADRENAL CORTEX-PITUITARY SYSTEM IN RATS. IT ALSO INHIBITED ASEPTIC INFLAMMATION (FORMALIN INJECTION UNDER THE PLANTAR APONEUROSIS OF THE FOOT) IN RATS; THIS ANTIINFLAMMATORY ACTIVITY APPEARS TO BE DUE TO ACTIVATION OF ADRENAL CORTEX-HYPOTHALAMUS-PITUITARY SYSTEM. IT MAY BE USEFUL TO ACTIVATE THE HORMONAL FUNCTION OF ADRENAL CORTEX-PITUITARY SYSTEM DURING GLUCOCORTICOID THERAPY IN PATIENTS WITH INFLAMMATION.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H14N2
Molecular Weight
162.2316
Exact Mass
162.116
CAS #
494-52-0
Related CAS #
(±) Anabasine;13078-04-1;Anabasine hydrochloride;53912-89-3
PubChem CID
205586
Appearance
Colorless to light yellow liquid
Density
1,0455 g/cm3
Boiling Point
270-272°C
Melting Point
9°C
Flash Point
93°C
Vapour Pressure
0.00662mmHg at 25°C
Index of Refraction
1.5430
LogP
2.225
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Heavy Atom Count
12
Complexity
136
Defined Atom Stereocenter Count
1
SMILES
N1CCCC[C@H]1C1C=NC=CC=1
InChi Key
MTXSIJUGVMTTMU-JTQLQIEISA-N
InChi Code
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/t10-/m0/s1
Chemical Name
3-[(2S)-piperidin-2-yl]pyridine
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~616.41 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.41 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (15.41 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (15.41 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.1641 mL 30.8204 mL 61.6409 mL
5 mM 1.2328 mL 6.1641 mL 12.3282 mL
10 mM 0.6164 mL 3.0820 mL 6.1641 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT01303081 Completed Behavioral: Individual Rewards
Behavioral: Fixed Deposits
Behavioral: Chosen Deposits
Tobacco Use Disorder University of Pennsylvania 2011-06 Not Applicable
NCT01526265 Completed Behavioral: Usual Care
Behavioral: Individual Rewards
Behavioral: Fixed Deposits
Tobacco Use Disorder University of Pennsylvania 2012-02 Not Applicable
NCT04605458 Recruiting Combination Product: Contingency Management
Combination Product: Standard Care
Smoking Cessation Medical University of South Carolina 2020-11-25 Not Applicable
NCT03473483 Withdrawn Other: SREC Cardiovascular Risk Factor
Nicotine Dependence
Nicotine Dependence, Cigarettes
Nicotine Withdrawal
Tobacco Toxicity
University of California, San Francisco 2022-08-01 Not Applicable
NCT05881304 Recruiting Device: Standardized research e-cigarette (SREC) Electronic Cigarette Use Massachusetts General Hospital 2024-06-03 Not Applicable
Biological Data
  • Anabasine and anatabine interactions with dizocilpine and working memory in the radial-arm maze. In both panels the control and dizocilpine alone data are the same. Data represent mean±sem, N=12. Dizocilpine alone caused a significant (p<0.025) increase in working memory errors. This impairment was significantly reversed by 0.2 mg/kg (p<0.05) and 2 mg/kg (p<0.025) of anabasine, but anatabine at these doses was not observed to produce a significant reduction in errors caused by dizocilpine.[1]. Effects of tobacco smoke constituents, anabasine and anatabine, on memory and attention in female rats. J Psychopharmacol. 2014 Oct;28(10):915-22.
  • Anabasine and anatabine interactions with dizocilpine and reference memory in the radial-arm maze. In both panels the control and dizocilpine alone data are the same. Data represent mean±sem, N=12. There was a significant main effect of dizocilpine increasing reference memory errors (p<0.01), but there were no significant effects of these doses of anabasine or anatabine on reference errors.[1]. Effects of tobacco smoke constituents, anabasine and anatabine, on memory and attention in female rats. J Psychopharmacol. 2014 Oct;28(10):915-22.
  • Anabasine and anatabine interactions with dizocilpine and latency in the radial-arm maze). In both panels the control and dizocilpine alone data are the same. Data represent seconds per arm entry mean±sem, N=12. There was a significant main effect of dizocilpine quickening response (p<0.005), but there were no significant effects of these doses of anabasine or anatabine on response speed.[1]. Effects of tobacco smoke constituents, anabasine and anatabine, on memory and attention in female rats. J Psychopharmacol. 2014 Oct;28(10):915-22.
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