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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N2
Molecular Weight 162.2316
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANABASINE

SMILES

C1CC[C@H](NC1)C2=CC=CN=C2

InChI

InChIKey=MTXSIJUGVMTTMU-JTQLQIEISA-N
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

HIDE SMILES / InChI

Molecular Formula C10H14N2
Molecular Weight 162.2316
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Anabasine, a tobacco alkaloid, was used as a biomarker of active tobacco use. Anabasine is a selective alpha7-nicotinic acetylcholine receptor agonist. Anabasine antagonized MK-801-elicited mouse popping behavior, an animal model of schizophrenia.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.0 µM [Ki]
2.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Goats: Different, single doses of anabasine, anabaseine, epibatidine, DMPP, or saline control were administered I.V. to pregnant goats on day 40 of gestation and the number of fetal movements per 5 min sample was measured by ultrasound at times 0, 0.5, 1, 2, 4 and 8 h. The differences among does in fetal movements were more consistent at dosing and following recovery for doses of anabasine above 0.125 mg/kg compared to the other compounds and dosages. Anabasine actions were dose-dependent with an IC50 value of ∼0.1 mg/kg, and, at a dose of 0.8 mg/kg, completely inhibited fetal movement for 1.5 h after dosing.
Route of Administration: Intravenous
In Vitro Use Guide
The effects of anabasine on aromatase in placental microsomes was assessed in tissue obtained from two women. In these two experiments the apparent Ki`s for anabasine inhibition of aromatase were 2 and 3 uM.
Substance Class Chemical
Record UNII
LMS11II2LO
Record Status Validated (UNII)
Record Version