Terbinafine

Athanor · official

C₂₁H₂₅N · 291.4 g/mol

IUPAC name: (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine

Also called Lamisil, allylamine antifungal

Drugs Rings

Open in Athanor

Drawn from its SMILES with RDKit

WarningCauses skin irritation · Causes serious eye irritation · May cause respiratory irritation · Suspected of damaging the unborn child · May cause harm to breast-fed children · May causes damage to organs through prolonged or repeated exposure · Very toxic to aquatic life · Very toxic to aquatic life with long lasting effects

Names and identifiers

IUPAC name: (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine
Synonyms: Lamisil, allylamine antifungal, Lamasil
+ 36 more
SF-86-327, Terbinafina, (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine, Terbinafinum, DTXSID2023640, (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene methanamine, G7RIW8S0XP, TDT 067, TDT-067, 1-NAPHTHALENEMETHANAMINE, N-(6,6-DIMETHYL-2-HEPTEN-4-YNYL)-N-METHYL-, (E)-, CHEBI:9448, DTXCID703640, OSURNIA COMPONENT TERBINAFINE, 1-Naphthalenemethanamine, N-((2E)-6,6-dimethyl-2-hepten-4-yn-1-yl)-N-methyl-, 1-Naphthalenemethanamine, N-[(2E)-6,6-dimethyl-2-hepten-4-yn-1-yl]-N-methyl-, RefChem:56103, TDT067, (6,6-dimethylhept-2-en-4-yn-1-yl)(methyl)(naphthalen-1-ylmethyl)amine, D01AE15, D01BA02, SF86327, SF 86327, SF 86 327, (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine, SF 86-327, MFCD00242672, N-[(2E)-6,6-dimethyl-2-hepten-4-yn-1-yl]-N-methyl-1-naphthalenemethanamine, terbinafin, TERBINAFINE [USAN], CHEMBL822, Lamisil Tablet, NCGC00159346-02, (2E)-N,6,6-trimethyl-N-(1-naphthylmethyl)hept-2-en-4-yn-1-amine, (E)-N,6,6-trimethyl-N-(1-naphthylmethyl)hept-2-en-4-yn-1-amine, (2E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine, [(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)[(naphthalen-1-yl)methyl]amine
Molecular formula: C₂₁H₂₅N
Empirical formula: C₂₁H₂₅N
Molecular weight: 291.4 g/mol
Exact mass: 291.19870
CAS number: 91161-71-6
PubChem CID: 1549008
Canonical SMILES: CC(C)(C)C#CC=CCN(C)CC1=CC=CC2=CC=CC=C21
Isomeric SMILES: CC(C)(C)C#C/C=C/CN(C)CC1=CC=CC2=CC=CC=C21
InChI: InChI=1S/C21H25N/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19/h5-7,9-14H,16-17H2,1-4H3/b9-5+
InChIKey: DOMXUEMWDBAQBQ-WEVVVXLNSA-N
Molfile

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

Calculated

Heavy atoms: 22
Rings: 2
Aromatic rings: 2
Fraction sp³ carbons (Fsp3): 0.33
H-bond donors: 0
H-bond acceptors: 1
Rotatable bonds: 4 computed here · PubChem 5
TPSA (Å²): 3.2
Formal charge: 0
XLogP3: 5.6 PubChem
Complexity: 428 PubChem
Stereocenters: None
Double-bond geometry: C4=C5: E
Point group: C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

C86.55%
H8.65%
N4.81%

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: 4.88 Crippen (Wildman and Crippen 1999)
log S (water solubility): -4.79 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 2.54 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 291.44
log P ≤ 5 (Crippen): 4.88
H-bond donors ≤ 5: 0
H-bond acceptors ≤ 10: 1

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: 3 company reports to ECHA. Source [1].

Harmful or irritant
Health hazard
Environmental hazard

H315Causes skin irritation (33.3% of reports)
H319Causes serious eye irritation (33.3% of reports)
H335May cause respiratory irritation (33.3% of reports)
H361dSuspected of damaging the unborn child (33.3% of reports)
H362May cause harm to breast-fed children (33.3% of reports)
H373May causes damage to organs through prolonged or repeated exposure (33.3% of reports)
H400Very toxic to aquatic life
H410Very toxic to aquatic life with long lasting effects

Precautionary statements: P203, P260, P261, P263, P264, P264+P265, P270, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, P501

Safety data sheets on the supplier’s page: Enamine, LGC Standards, AbaChemScene.

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]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
[2]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
[3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
[4]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
[5]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[6]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.