Lidocaine (C14H22N2O): structure, properties and hazards

Names and identifiers

IUPAC name: 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide
Synonyms: Xylocaine, lignocaine, anaesthetic
+ 37 more
2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide, Duncaine, Lidoderm, Xylestesin, Esracaine, Gravocain, Isicaina, Leostesin, Maricaine, Solcain, Cappicaine, Solarcaine, Isicaine, Rucaina, Xycaine, L-Caine, Alphacaine, Xylotox, Lida-Mantle, Dentipatch, 2-(Diethylamino)-2',6'-acetoxylidide, Lidocainum, Cuivasil, Jetocaine, Lidocaina, Remicaine, Xilocaina, 2-Diethylamino-N-(2,6-dimethylphenyl)acetamide, Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)-, ZTlido, Diethylaminoaceto-2,6-xylidide, 2',6'-Acetoxylidide, 2-(diethylamino)-, Ztilido, alpha-Diethylamino-2,6-dimethylacetanilide, DTXSID1045166, alfa-Dietilamino-2,6-dimetilacetanilide, NSC-40030
Molecular formula: C₁₄H₂₂N₂O
Empirical formula: C₁₄H₂₂N₂O
Molecular weight: 234.34 g/mol
Exact mass: 234.17321
CAS number: 137-58-6
PubChem CID: 3676
Canonical SMILES: CCN(CC)CC(=O)NC1=C(C=CC=C1C)C
Isomeric SMILES: CCN(CC)CC(=O)NC1=C(C=CC=C1C)C
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)
InChIKey: NNJVILVZKWQKPM-UHFFFAOYSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Physical properties

Appearance: Needles from benzene or alcohol[1]
2 values
From Hazardous Substances Data Bank (HSDB), the most authoritative source here.
Value As written Source
–shown Needles from benzene or alcohol [1] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1239
– White or slightly yellow, crystalline powder [1] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 754
Odor: Characteristic odor[1]
Solubility in water: In water, 410 mg/L at 30 °C[1]
3 values
From Hazardous Substances Data Bank (HSDB), the most authoritative source here.
Value As written Source
– VERY SOL IN ALC; SOL IN CHLOROFORM; INSOL IN ETHER; WHITE CRYSTALLINE POWDER /LIDOCAINE HYDROCHLORIDE/ [1] Hazardous Substances Data Bank (HSDB)cites Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 995
–shown In water, 410 mg/L at 30 °C [1] Hazardous Substances Data Bank (HSDB)cites Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 1030
– Soluble in alcohol, ether, or chloroform [1] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 754
log P: log Kow = 2.26 at pH 7.4[1]
pKa: pKa = 7.86[1]

Value	As written	Source
–shown	Needles from benzene or alcohol	[1] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1239
–	White or slightly yellow, crystalline powder	[1] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 754

Value	As written	Source
–	VERY SOL IN ALC; SOL IN CHLOROFORM; INSOL IN ETHER; WHITE CRYSTALLINE POWDER /LIDOCAINE HYDROCHLORIDE/	[1] Hazardous Substances Data Bank (HSDB)cites Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 995
–shown	In water, 410 mg/L at 30 °C	[1] Hazardous Substances Data Bank (HSDB)cites Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 1030
–	Soluble in alcohol, ether, or chloroform	[1] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 754

Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.

Calculated

Heavy atoms: 17
Rings: 1
Aromatic rings: 1
Fraction sp³ carbons (Fsp3): 0.5
H-bond donors: 1
H-bond acceptors: 2
Rotatable bonds: 5
TPSA (Å²): 32.3
Formal charge: 0
XLogP3: 2.3 PubChem
Complexity: 228 PubChem
Stereocenters: None
Double-bond geometry: None specified
Point group: C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

C71.76%
H9.46%
N11.95%
O6.83%

Isotope pattern

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P: 2.58 Crippen (Wildman and Crippen 1999)
log S (water solubility): -2.85 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 1.81 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 234.34
log P ≤ 5 (Crippen): 2.58
H-bond donors ≤ 5: 1
H-bond acceptors ≤ 10: 2

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

Most widely reported: 167 company reports to ECHA. Source [2].

Harmful or irritant

H302Harmful if swallowed (98.2% of reports)

Precautionary statements: P264, P270, P301+P317, P330, P501

View all classifications (4)

[2] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 1.2% (2 of 167) of reports.
[2] European Chemicals Agency (ECHA) · 167 reports · WarningH302
[2] European Chemicals Agency (ECHA) · WarningH302
[1] Hazardous Substances Data Bank (HSDB) · WarningH302

Storage

Lidocaine hydrochloride injections and commercially available solutions of the drug in 5% dextrose should be stored at 25 °C but may be exposed to temperatures up to 40 °C; the injection and solutions should not be frozen, and the solutions should be protected from excessive heat.[1]
Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place.[1]
Lidocaine hydrochloride injections should be stored at a 20-25 °C; solutions containing epinephrine should be protected from light.[1]

Incompatibilities

Incompatible materials: Strong oxidizing agents.[1]

Safety data sheets on the supplier’s page: eMolecules, Smolecule, Sigma-Aldrich.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

[1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
[2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
[3]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
[4]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
[5]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
[6]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[7]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
·Literature on PubChem

Data last updated 2026-10-14.