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Adrenaline

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C9H13NO3 · 183.2 g/mol

IUPAC name: 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

Also called epinephrine, EpiPen, catecholamine

Natural productsDrugs
Open in Athanor
The structure of Adrenaline
Drawn from its SMILES with RDKit
Acute toxicityDangerToxic if swallowed · Fatal in contact with skin · Toxic if inhaled

Names and identifiers

IUPAC name
4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
Synonyms
epinephrine, EpiPen, catecholamine
+ 38 more

l-Adrenaline, Adrenalin, Levoepinephrine, Nephridine, Epinefrina, Epipen, (-)-Adrenaline, Adnephrine, Chelafrin, Epinephran, Epirenan, Renoform, (R)-Adrenaline, Hypernephrin, Renostypticin, Adrenine, Hemisine, Hemostasin, Levorenin, Levorenine, Mucidrina, Nieraline, Paranephrin, Renaglandin, Renaleptine, Renalina, Bosmin, Exadrin, Adrin, Vasoconstrictine, Bronkaid Mist, Primatene Mist, Methylarterenol, Adrenalinum, Glauposine, Hemostatin, Scurenaline, Styptirenal

Molecular formula
C9H13NO3
Empirical formula
C9H13NO3
Molecular weight
183.2 g/mol
Exact mass
183.08954
CAS number
51-43-4
PubChem CID
5816
Canonical SMILES
CNCC(C1=CC(=C(C=C1)O)O)O
Isomeric SMILES
CNC[C@@H](C1=CC(=C(C=C1)O)O)O
InChI
InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1
InChIKey
UCTWMZQNUQWSLP-VIFPVBQESA-N
Molfile

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

Physical properties

TemperaturePressureDensity
Appearance
Colorless microcrystals[2]
4 values

From Hazardous Substances Data Bank (HSDB), the most authoritative source here.

ValueAs writtenSource
–Epinephrine appears as white to nearly-white microcrystalline powder or granules. Odorless. Melting point 211-212 °C. Aqueous solutions are slightly alkaline. Slightly bitter, numbing taste.[1] CAMEO Chemicals
–Light brown or nearly white crystalline powder[2] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 505
–shownColorless microcrystals[2] Hazardous Substances Data Bank (HSDB)cites Pugsley TA; Kirk-Othmer Encyclopedia of Chemical Technology. (2001). NY, NY: John Wiley & Sons; Epinephrine and Norepinephrine. Online Posting Date: Dec 4, 2000.
–White to nearly white, microcrystalline powder or granules.[2] Hazardous Substances Data Bank (HSDB)cites McEvoy, G.K. (ed.). AHFS Drug Information 90. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1990 (Plus Supplements 1990)., p. 625
Odor
Odorless[2]
Melting point
211 to 212 °C (412 to 414 °F, NTP 1992)[1]
Solubility in water
In water, 180 mg/L at 20 °C[2]
4 values

From Hazardous Substances Data Bank (HSDB), the most authoritative source here.

ValueAs writtenSource
–less than 0.1 mg/mL at 64 °F (NTP, 1992)[1] CAMEO Chemicalscites National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
–Very slightly soluble in alcohol.[2] Hazardous Substances Data Bank (HSDB)cites McEvoy, G.K. (ed.). AHFS Drug Information 90. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1990 (Plus Supplements 1990)., p. 625
–Insoluble in ethanol; soluble in acetic acid[2] Hazardous Substances Data Bank (HSDB)cites Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 907
–shownIn water, 180 mg/L at 20 °C[2] Hazardous Substances Data Bank (HSDB)cites Yalkowsky, S.H., He, Yan., Handbook of Aqueous Solubility Data: An Extensive Compilation of Aqueous Solubility Data for Organic Compounds Extracted from the AQUASOL dATAbASE. CRC Press LLC, Boca Raton, FL. 2003., p. 597
log P
log Kow = -2.59[2]
pKa
pKa = 8.28[2]

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
13
Rings
1
Aromatic rings
1
Fraction sp³ carbons (Fsp3)
0.33
H-bond donors
4
H-bond acceptors
4
Rotatable bonds
3
TPSA (Ų)
72.7
Formal charge
0
XLogP3
-1.4 PubChem
Complexity
154 PubChem
Stereocenters
1 definedCIP: 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

  • C59.00%
  • H7.15%
  • N7.65%
  • O26.20%

Isotope pattern

100%183.08910%184.0931.1%185.095

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
0.35 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-1.34 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
2.65 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 183.21
  • log P ≤ 5 (Crippen): 0.35
  • H-bond donors ≤ 5: 4
  • 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

Danger

Most widely reported: 103 company reports to ECHA. Source [3].

  • Acute toxicity
  • H301Toxic if swallowed (96.1% of reports)
  • H310Fatal in contact with skin (95.1% of reports)
  • H331Toxic if inhaled (93.2% of reports)

Precautionary statements: P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, P501

First aid

  • Eyes: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. Immediately transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. Skin: Immediately flood affected skin with water while removing and isolating all contaminated clothing.[1]

Storage

  • Epinephrine injection should be stored at room temperature (approximately 25 °C).[2]
  • Preserve in tight, light-resistant containers.[2]

Safety data sheets on the supplier’s page: Alfa Chemistry, Smolecule, TCI (Tokyo Chemical Industry).

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]CAMEO Chemicals · Public domain (NOAA) · via PubChem · retrieved 2026-10-14
  2. [2]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
  3. [3]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  4. [4]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  5. [5]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  6. [6]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  7. [7]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  8. [8]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  9. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  10. ·Literature on PubChem

Data last updated 2026-10-14.