(-)-ANABASINE Chemical Properties

Melting point:

9°C

Boiling point:

270-272°C

alpha 

D20 -83.1°

Density 

1,0455 g/cm³

refractive index 

1.5430

Flash point:

93°C

storage temp. 

2-8°C

solubility 

DMSO : 100 mg/mL (616.41 mM)

pka

8.98±0.10(Predicted)

form 

Liquid

color 

Colorless to light yellow

Merck 

14,619

BRN 

82637

CAS DataBase Reference

494-52-0(CAS DataBase Reference)

NIST Chemistry Reference

Pyridine, 3-(2-piperidinyl)-, (S)-(494-52-0)

EPA Substance Registry System

Anabasine (494-52-0)

Safety Information

Hazard Codes 

T

Risk Statements 

27/28-51/53-23/24/25

Safety Statements 

28-36/37-45-61-36/37/39-28A

RIDADR 

3140

RTECS 

BV4375000

HazardClass 

6.1

PackingGroup 

I

HS Code 

29333990

Hazardous Substances Data

494-52-0(Hazardous Substances Data)

Toxicity

LDLo orl-dog: 50 mg/kg JPETAB 48,95,33

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

(-)-ANABASINE Usage And Synthesis

Chemical Properties

Pale Yellow Oil

Uses

Anabasine occurs in the tobacco speciesNicotiana glauca, Anabasis aphylla L.,Chenopodiaceae, and Solanaceae. It is usedas an insecticide and as a metal anticorrosiveagent.

Uses

(S)-ANABASINE is used as a kind of Nicotinic receptor agonist.

Definition

ChEBI: The (S)-enantiomer of anabasine.

Health Hazard

The acute toxic symptoms include increasedsalivation, confusion, disturbed vision, photophobia,nausea, vomiting, diarrhea, respiratorydistress, and convulsions. It causesrespiratory muscle stimulation similar to thatcaused by lobeline. An oral lethal dose indogs is 50 mg/kg. A subcutaneous lethaldose in guinea pigs is 10 mg/kg.

Biological Activity

Anabasine ((S)-Anabasine) is an alkaloid, a component of tobacco. Anabasine is a botanical insecticide that acts as a pan-agonist of nicotinic acetylcholine receptors (nAChRs). Anabasine induces depolarization in TE671 cells endogenously expressing human myogenic nAChRs (EC50=0.7 μM).

Safety Profile

Poison by ingestion,subcutaneous, and intravenous routes. Moderately toxicby skin contact. An experimental teratogen. Insecticide.Acute and subacute toxicity: increased salivation, vertigo,confusion, disturbed vision and hearing, photophobia,cold ext

in vivo

Anabasine significantly reverses the impairment at the 0.2 mg/kg (p<0.05) and 2 mg/kg doses (p<0.025). Anabasine does not have any significant effects on response latency when administered alone. The 0.06 mg/kg Anabasine dose, in fact, significantly (p<0.05) exacerbates the dizocilpine-induced impairment. None of these Anabasine doses affects choice accuracy on their own. Individual dose comparisons show that the 0.06 mg/kg Anabasine dose plus dizocilpine (6.7±2.6) causes a significant (p<0.05) increase in non-response trials compare with dizocilpine alone (2.1±0.8).

(-)-ANABASINE(494-52-0)Related Product Information

• Protionamide Sulfoxide
• (-)-ANABASINE
• AKOS 213-73
• (S)-3-(3,4,5,6-TETRAHYDRO-2H-[2,3']BIPYRIDINYL-1-YL)-PROPIONIC ACID METHYL ESTER
• (R,S)-N-NITROSOANABASINE
• 4-OXO-4-(S)-3,4,5,6-TETRAHYDRO-2H-[2,3']BIPYRIDINYL-1-YL-BUTYRIC ACID
• (+/-)-ANABASINE DIPICRATE
• (-)-ANABASINE
• N-Methylanabasine
• 4-METHOXY-3-[(S)-1-(3,4,5,6-TETRAHYDRO-2H-[2,3']BIPYRIDINYL-1-YL)METHYL]-BENZALDEHYDE
• (S)-2-(3,4,5,6-TETRAHYDRO-2H-[2,3']BIPYRIDINYL-1-YL)-ETHANOL
• (+)-Anabasinehydrochloride
• AKOS 213-74
• 3-[(2S)-PIPERIDIN-2-YL]PYRIDINE HYDROCHLORIDE
• ANABASINE SULFATE