Lidocaine
C₁₄H₂₂N₂O·234.343 g/mol·Pharmaceutical·CID 3676
DrugAnesthetic
The most widely used local anesthetic. Blocks voltage-gated sodium channels, preventing nerve impulse transmission. Also used as an antiarrhythmic drug (Class Ib). Available as injections, topical creams, and dental cartridges.
IUPAC: 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide
Also known as: 137-58-6, Xylocaine, 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide, Duncaine, Lidoderm (+14 more)
Molecular Structure
Molecular Propertiesmass · H-bonds · stereo
Molecular Weight
234.340g/mol
Exact Mass
234.173213Da
Monoisotopic Mass
234.173213Da
XLogP
2.3
Polar Surface Area
32.3Ų
Complexity
228
Formal Charge
0
H-Bond Donors
1
H-Bond Acceptors
2
Rotatable Bonds
5
Heavy Atoms
17
Stereo Centers
0
Bond Stereo
0
Drug-Likeness (Lipinski's Rule of Five)
✓ 234.3 g/mol
MW ≤ 500
✓ 2.3
LogP ≤ 5
✓ 1
H-bond donors ≤ 5
✓ 2
H-bond acceptors ≤ 10
Passes all rules — good oral bioavailability predicted
GHS Hazard Classification
Danger
Hazards
H302Harmful if swallowedH317May cause an allergic skin reactionH362May cause harm to breast-fed childrenH370Causes damage to organsH372Causes damage to organs through prolonged or repeated exposure
Source: PubChem GHS Classification. Always consult the SDS for handling.
Chemical IdentifiersSMILES · InChI
InChI
InChI=1S/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)
Constituent Elements
Isomers8 compounds with formula C₁₄H₂₂N₂O
(E,2S)-N-methyl-5-(5-propan-2-yloxy-3-pyridinyl)pent-4-en-2-amine
CID 9824145 · 234.3 g/mol
(1S,2R,9S,10S)-10-prop-2-enyl-7,11-diazatricyclo[7.3.1.02,7]tridecan-6-one
CID 12306807 · 234.3 g/mol
1-(2-methoxyphenyl)-4-propylpiperazine
CID 410747 · 234.3 g/mol
3-(diethylamino)-N-phenylbutanamide
CID 26329 · 234.3 g/mol
1-(2-butoxyphenyl)piperazine
CID 14479837 · 234.3 g/mol
3-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]-5-propylpyridine
CID 44318740 · 234.3 g/mol
1-(4-methoxyphenyl)-4-propylpiperazine
CID 12854846 · 234.3 g/mol
2-(diethylamino)-N-(2,4-dimethylphenyl)acetamide
CID 28447 · 234.3 g/mol