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Cocaine

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C17H21NO4 · 303.35 g/mol

IUPAC name: methyl 3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Also called benzoylmethylecgonine, coca alkaloid

DrugsNatural products
Open in Athanor
The structure of Cocaine
Drawn from its SMILES with RDKit

Names and identifiers

IUPAC name
methyl 3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Synonyms
benzoylmethylecgonine, coca alkaloid, Allococaine
+ 32 more

Methyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate, Pseudococaine -, (+)-Cocaine, Cocainzusatze, rac-Allococaine, (-)-Cocaine base, NCGC00159467-02, NCGC00159467-03, SCHEMBL21931, MLS002320697, CHEMBL32363, DivK1c_000975, SCHEMBL8391141, Methyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate #, BDBM86207, KBio1_000975, NINDS_000975, ZPUCINDJVBIVPJ-UHFFFAOYSA-N, HMS2272A05, AAA66819, NFA70414, WAA03042, STL565195, AKOS025401423, NSC_446220, CAS_50-36-2, IDI1_000975, AC-16037, SMR001338843, NS00133570, L000836, methyl 8-methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylate

Molecular formula
C17H21NO4
Empirical formula
C17H21NO4
Molecular weight
303.35 g/mol
Exact mass
303.14706
CAS number
50-36-2
PubChem CID
2826
Canonical SMILES
CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC
Isomeric SMILES
CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC
InChI
InChI=1S/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3
InChIKey
ZPUCINDJVBIVPJ-UHFFFAOYSA-N
Molfile

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

Calculated

Heavy atoms
22
Rings
3
Aromatic rings
1
Fraction sp³ carbons (Fsp3)
0.53
H-bond donors
0
H-bond acceptors
5
Rotatable bonds
3 computed here · PubChem 5
TPSA (Ų)
55.8
Formal charge
0
XLogP3
2.3 PubChem
Complexity
432 PubChem
Stereocenters
0 defined, 4 undefinedCIP: C5: undefined · C6: undefined · C17: undefined · C20: undefined
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

  • C67.31%
  • H6.98%
  • N4.62%
  • O21.10%

Isotope pattern

100%303.14719%304.1502.6%305.153306.156

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
1.87 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-2.9 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
3.99 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 303.36
  • log P ≤ 5 (Crippen): 1.87
  • H-bond donors ≤ 5: 0
  • H-bond acceptors ≤ 10: 5

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

No GHS hazard classification was found in the sources.

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. [1]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  2. [2]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  3. [3]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  5. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  6. ·Literature on PubChem

Data last updated 2026-10-14.