Pilocarpine (C11H16N2O2): structure, properties and hazards

Names and identifiers

IUPAC name: (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one
Synonyms: Salagen, Isopto Carpine, muscarinic agonist
+ 38 more
Pilokarpin, Pilocarpol, Syncarpine, Ocusert pilo, Pilocarpin, Spersacarpine, Ocusert pilo-20, Ocusert Pilo-40, Ocusert P 20, ocucarpine, Pilocarpine muriate, Pilovisc, Pilocarpinum, DTXSID1021162, Spersacarpine hydrochloride, Pilokarpin monohydrochloride, 01MI4Q9DI3, (3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one, (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one, Imidazole-5-butyric acid, alpha-ethyl-beta-(hydroxymethyl)-1-methyl-, gamma-lactone, CHEBI:8207, DTXCID901162, (3S,4R)-3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone, Hydrochloride, Pilocarpine, (3S,4R)-3-ethyl-4-((3-methylimidazol-4-yl)methyl)oxolan-2-one, (3S,4R)-3-ethyl-4-((1-methyl-1H-imidazol-5-yl)methyl)oxolan-2-one, Nitrate, Pilocarpine, RefChem:56450, CHEBI:39462, Pilocarpine Mononitrate, (3S-cis)-, Pilocarpine, Monohydrochloride, (3S-cis)-, 202-128-4, (+)-Pilocarpine, Adsorbocarpine, Isoptocarpine, Epicar, Pilocarpine chloride, (3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydrofuran-2(3H)-one
Molecular formula: C₁₁H₁₆N₂O₂
Empirical formula: C₁₁H₁₆N₂O₂
Molecular weight: 208.26 g/mol
Exact mass: 208.12118
CAS number: 92-13-7
PubChem CID: 5910
Canonical SMILES: CCC1C(COC1=O)CC2=CN=CN2C
Isomeric SMILES: CC[C@H]1[C@H](COC1=O)CC2=CN=CN2C
InChI: InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8-,10-/m0/s1
InChIKey: QCHFTSOMWOSFHM-WPRPVWTQSA-N
Molfile

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

Calculated

Heavy atoms: 15
Rings: 2
Aromatic rings: 1
Fraction sp³ carbons (Fsp3): 0.64
H-bond donors: 0
H-bond acceptors: 3
Rotatable bonds: 3
TPSA (Å²): 44.1
Formal charge: 0
XLogP3: 1.1 PubChem
Complexity: 245 PubChem
Stereocenters: 2 definedCIP: C3: S · C4: R
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

C63.44%
H7.74%
N13.45%
O15.36%

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: 1.16 Crippen (Wildman and Crippen 1999)
log S (water solubility): -1.91 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 3.64 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 208.26
log P ≤ 5 (Crippen): 1.16
H-bond donors ≤ 5: 0
H-bond acceptors ≤ 10: 3

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

Danger

Harmonized EU classification (CLP Annex VI). Source [2].

Acute toxicity

H300Fatal if swallowed
H330Fatal if inhaled

Precautionary statements: P260, P264, P270, P271, P284, P301+P316, P304+P340, P316, P320, P321, P330, P403+P233, P405, P501

View all classifications (2)

[2] Regulation (EC) No 1272/2008 of the European Parliament and of the Council · DangerH300, H330
[3] European Chemicals Agency (ECHA) · 40 reports · DangerH300+H330, H300, H330

Safety data sheets on the supplier’s page: LGC Standards, AstaTech, Inc., CATO Research Chemicals Inc..

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]Regulation (EC) No 1272/2008 of the European Parliament and of the Council · EU reuse policy, CC BY 4.0 · via PubChem · retrieved 2026-10-14
[3]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · 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.