Procaine (C13H20N2O2): structure, properties and hazards

Names and identifiers

IUPAC name: 2-(diethylamino)ethyl 4-aminobenzoate
Synonyms: Novocain, local anaesthetic, 2-(Diethylamino)ethyl 4-aminobenzoate
+ 36 more
Spinocaine, Procain, Vitamin H3, Duracaine, Nissocaine, Novocaine, Procaine, base, Procaina, Scurocaine, Benzoic acid, 4-amino-, 2-(diethylamino)ethyl ester, Procainum, 2-Diethylaminoethyl 4-aminobenzoate, Diethylaminoethyl p-aminobenzoate, 2-Diethylaminoethyl p-aminobenzoate, p-Aminobenzoic acid 2-diethylaminoethyl ester, 4-Aminobenzoic acid diethylaminoethyl ester, Benzoic acid, p-amino-, 2-(diethylamino)ethyl ester, beta-Diethylaminoethyl 4-aminobenzoate, NSC-169497, CHEBI:8430, beta-(Diethylamino)ethyl 4-aminobenzoate, beta-(Diethylamino)ethyl p-aminobenzoate, 4-Aminobenzoic acid 2-diethylaminoethyl ester, 4Z8Y51M438, DTXSID7045021, 4-14-00-01138 (Beilstein Handbook Reference), RefChem:6164, DTXCID5025021, C05AD05, N01BA02, S01HA05, novocainum (for the hydrochloride), 200-426-9, Gerovital, Norocaine, p-Aminobenzoyldiethylaminoethanol
Molecular formula: C₁₃H₂₀N₂O₂
Empirical formula: C₁₃H₂₀N₂O₂
Molecular weight: 236.31 g/mol
Exact mass: 236.15248
CAS number: 59-46-1
PubChem CID: 4914
Canonical SMILES: CCN(CC)CCOC(=O)C1=CC=C(C=C1)N
Isomeric SMILES: CCN(CC)CCOC(=O)C1=CC=C(C=C1)N
InChI: InChI=1S/C13H20N2O2/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3
InChIKey: MFDFERRIHVXMIY-UHFFFAOYSA-N
Molfile

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

Physical properties

Solubility in water: In water, 9.45 × 10³ mg/l @ 30 °C[1]
2 values
From Hazardous Substances Data Bank (HSDB), the most authoritative source here.
Value As written Source
– ODORLESS; AQ SOLN ACID TO LITMUS; PKA 8.7; SMALL WHITE CRYSTALS; 1 G SOL IN 1 ML WATER OR 15 ML ALC; SLIGHTLY SOL IN CHLOROFORM; PRACTICALLY INSOL IN ETHER /HYDROCHLORIDE/ [1] Hazardous Substances Data Bank (HSDB)cites Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 994
–shown In water, 9.45X10+3 mg/l @ 30 °C [1] Hazardous Substances Data Bank (HSDB)cites Yalkowsky SH, Dannenfelser RM; The AQUASOL dATAbASE of Aqueous Solubility. Fifth ed, Tucson, AZ: Univ AZ, College of Pharmacy (1992)
log P: log Kow= 1.92[1]
pKa: pKa= 8.05 at 15 °C (conjugate acid)[1]

Value	As written	Source
–	ODORLESS; AQ SOLN ACID TO LITMUS; PKA 8.7; SMALL WHITE CRYSTALS; 1 G SOL IN 1 ML WATER OR 15 ML ALC; SLIGHTLY SOL IN CHLOROFORM; PRACTICALLY INSOL IN ETHER /HYDROCHLORIDE/	[1] Hazardous Substances Data Bank (HSDB)cites Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 994
–shown	In water, 9.45X10+3 mg/l @ 30 °C	[1] Hazardous Substances Data Bank (HSDB)cites Yalkowsky SH, Dannenfelser RM; The AQUASOL dATAbASE of Aqueous Solubility. Fifth ed, Tucson, AZ: Univ AZ, College of Pharmacy (1992)

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): 0.46
H-bond donors: 1
H-bond acceptors: 4
Rotatable bonds: 6 computed here · PubChem 7
TPSA (Å²): 55.6
Formal charge: 0
XLogP3: 1.9 PubChem
Complexity: 221 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

C66.07%
H8.53%
N11.85%
O13.54%

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: 1.77 Crippen (Wildman and Crippen 1999)
log S (water solubility): -2.28 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 1.86 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 236.31
log P ≤ 5 (Crippen): 1.77
H-bond donors ≤ 5: 1
H-bond acceptors ≤ 10: 4

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

From European Chemicals Agency (ECHA). Source [2].

Harmful or irritant

H302Harmful if swallowed

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

Safety data sheets on the supplier’s page: Vitas-M Laboratory, MolCore, MP Biomedicals.

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]NMRShiftDB · Linked only · via PubChem · retrieved 2026-10-14
[4]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
[5]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
[6]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
[7]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[8]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.

Similar structures

Tanimoto similarity on Morgan fingerprints (radius 2) with RDKit 2026.09, at least 45%.