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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H20NO2
Molecular Weight 174.2606
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of MUSCARINE

SMILES

C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O

InChI

InChIKey=UQOFGTXDASPNLL-XHNCKOQMSA-N
InChI=1S/C9H20NO2/c1-7-9(11)5-8(12-7)6-10(2,3)4/h7-9,11H,5-6H2,1-4H3/q+1/t7-,8-,9+/m0/s1

HIDE SMILES / InChI

Description

Muscarine or muscarin, a water-soluble toxin, which initially was isolated from the mushroom species Amanita muscar. Muscarine mimics the action of the acetylcholine by binding to the muscarinic acetylcholine receptors and acts as an agonist.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
toxicity in mice: the mouse i.v. LD50 for muscarine chloride was calculated to be 0.23 mg/kg and for acetylcholine chloride 33.05 mg/kg, thus muscarine was 143 times more toxic than acetylcholine. Signs of poisoning were similar, acetylcholine being lethal almost immediately and muscarine after 3 to 10 min. Death never occurred later than 10 min after the injection.
Route of Administration: Intravenous
In Vitro Use Guide
Muscarine (1-30 microM) produced a dose-dependent hyperpolarization in a subpopulation of the nucleus raphe magnus (NRM) cells that contain 5-hydroxytryptamine (5-HT). In voltage clamp, the muscarine-induced outward current reversed polarity at the potassium equilibrium potential and was characterized by strong inward rectification. The concentration-response curve for muscarine (EC50 = 2.7 microM) was shifted in a parallel manner to the right by increasing concentrations of pirenzepine (300 nM to 3 microM) and methoctramine (50-200 nM).