Octopamine
Athanor · official
C8H11NO2 · 153.18 g/mol
IUPAC name: 4-[(1R)-2-amino-1-hydroxyethyl]phenol
Also called norsynephrine, invertebrate neurotransmitter
Names and identifiers
- IUPAC name
- 4-[(1R)-2-amino-1-hydroxyethyl]phenol
- Synonyms
- norsynephrine, invertebrate neurotransmitter, (R)-octopamine
+ 38 more
D-Octopamine, (R)-p-Octopamine, D-(-)-Octopamine, Octopamine, (-)-, H1P36W1J84, Benzenemethanol, alpha-(aminomethyl)-4-hydroxy-, (alphaR)-, CHEBI:44715, DTXSID901317465, Octopamine d(-)-, RefChem:1051103, DTXCID601747277, 4-[(1R)-2-amino-1-hydroxyethyl]phenol, p-Octopamine, Octopamine d(-)-form [MI], p-Hydroxyphenylethanolamine, UNII-H1P36W1J84, dl-Octopamine, 4-(2R-AMINO-1-HYDROXYETHYL)PHENOL, CHEMBL1160703, (-)-octopamine, 2-Amino-1-(4-hydroxyphenyl)ethanol, Racemic octopamine, (RS)-Octopamine, OTR, R-OCTOPAMINE, 4-Hydroxyphenethanolamine, Lopac-O-0250, CAS-770-05-8, OCTOPAMINE, (R)-, SCHEMBL1650462, QHGUCRYDKWKLMG-QMMMGPOBSA-N, BDBM50581602, NCGC00015760-01, NCGC00015760-02, NCGC00015760-18, NCGC00016538-01, NS00003618, C04227
- Molecular formula
- C8H11NO2
- Empirical formula
- C8H11NO2
- Molecular weight
- 153.18 g/mol
- Exact mass
- 153.07898
- CAS number
- 104-14-3
- PubChem CID
- 440266
- Canonical SMILES
- C1=CC(=CC=C1C(CN)O)O
- Isomeric SMILES
- C1=CC(=CC=C1[C@H](CN)O)O
- InChI
- InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2/t8-/m0/s1
- InChIKey
- QHGUCRYDKWKLMG-QMMMGPOBSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 11
- Rings
- 1
- Aromatic rings
- 1
- Fraction sp³ carbons (Fsp3)
- 0.25
- H-bond donors
- 3
- H-bond acceptors
- 3
- Rotatable bonds
- 2
- TPSA (Ų)
- 66.5
- Formal charge
- 0
- XLogP3
- -1.1 PubChem
- Complexity
- 111 PubChem
- Stereocenters
- 1 definedCIP: C3: 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
- C62.73%
- H7.24%
- N9.14%
- O20.89%
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
- 0.38 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -1.3 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 2.41 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 153.18
- log P ≤ 5 (Crippen): 0.38
- H-bond donors ≤ 5: 3
- 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
No GHS hazard classification was found in the sources.
Safety data sheets on the supplier’s page: BenchChem, Enamine, RR Scientific.
Always read the supplier’s safety data sheet before working with it.
Spectra
- GC-MSMassBank of North America (MoNA) (GC-MS) · MassBank of North America (MoNA) (GC-MS)
- MS-MSHuman Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive)
- LC-MSMassBank of North America (MoNA) (Thermo Q Exactive HF · LC-ESI-QFT · positive) · MassBank of North America (MoNA) (Thermo Q Exactive HF · LC-ESI-QFT · positive) · MassBank of North America (MoNA) (Thermo Q Exactive HF · LC-ESI-QFT · positive)
- Other MSMassBank of North America (MoNA) (Orbitrap · positive) · MassBank of North America (MoNA) (Orbitrap · positive)
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]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- [2]Human Metabolome Database (HMDB) · Linked only · 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.