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A5656

Sigma-Aldrich

(±)-Anabasine

≥90% (TLC), liquid

Synonym(s):

3-(2-Piperidinyl)pyridine, Neonicotine

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About This Item

Empirical Formula (Hill Notation):
C10H14N2
CAS Number:
13078-04-1
Molecular Weight:
162.23
MDL number:
MFCD00006370
UNSPSC Code:
12352100
PubChem Substance ID:
24891007

Assay

≥90% (TLC)

form

liquid

optical activity

[α]25/D 0°, c = 1 in H2O(lit.)

color

colorless to yellow

transition temp

freezing point 9 °C

solubility

H2O: 10 mg/mL
ethanol: 50 mg/mL

density

1.05 g/mL at 25 °C (lit.)

application(s)

agriculture
environmental

SMILES string

C1CCC(NC1)c2cccnc2

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

Gene Information

mouse ... Chrna7(11441) , Chrnb1(11443)

Biochem/physiol Actions

Tobacco alkaloid; potent nicotinic acetylcholine receptor agonist.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

199.4 °F - closed cup

Flash Point(C)

93 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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W R Kem et al.
The Journal of pharmacology and experimental therapeutics, 283(3), 979-992 (1998-02-12)
We assessed the pharmacological activity of anabaseine, a toxin found in certain animal venoms, relative to nicotine and anabasine on a variety of vertebrate nicotinic receptors, using cultured cells, the Xenopus oocyte expression system, contractility assays with skeletal and smooth
M J Parker et al.
Molecular pharmacology, 54(6), 1132-1139 (1998-12-18)
We used equilibrium binding analysis to characterize the agonist binding properties of six different rat neuronal nicotinic receptor subunit combinations expressed in Xenopus laevis oocytes. The alpha4beta2 receptor bound [3H]cytisine with a Kdapp of 0.74 +/- 0. 14 nM. The
P M Gocze et al.
Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology, 13(4), 266-272 (1999-10-26)
To reveal the well known effect of smoking on the incidence of early abortion, the possible effects of cigarette alkaloids on progesterone and estradiol synthesis were investigated. A suspected cause for early spontaneous abortion is corpus luteum insufficiency. The present
N Mizrachi et al.
Journal of forensic sciences, 45(3), 736-741 (2000-06-16)
Death of a worker occurred after ingestion of unknown amounts of Nicotiana glauca G leaves. The leaves were cooked after having been mistakenly considered to be spices of a type which grow in Thailand. After ingestion, two Thai workers collapsed
Y Lu et al.
The Journal of pharmacology and experimental therapeutics, 291(3), 1127-1134 (1999-11-24)
Several neurochemical and electrophysiological studies have shown that neuronal nicotinic receptors are desensitized by pretreatment with lower agonist concentrations than are required to activate the receptors, but the extent of desensitization and agonist concentration required to produce desensitization vary depending
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