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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
J L Castorena et al.
Journal of toxicology. Clinical toxicology, 25(5), 429-435 (1987-01-01)
A young adult male was found dead in a field. No cause of death was apparent at autopsy, and the only positive toxicological finding was the presence of a nicotine-like alkaloid isolated from the liver. Anabasine, the major, highly toxic
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
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