Epinephrine

Epinephrine	Last updated: 16/09/2025
(Also known as: adrenaline)

GENERAL INFORMATION

Description

Epinephrine is widely used drug for anaphylactoid shock

Examples of veterinary uses

Primarily used to treat anaphylaxis and for cardiac resuscitation

Examples of species treated

Dogs; Cats; Other domesticated animals; Cattle; Horses; Pigs; Sheep

Approval status

VMR 2013/2033 approval status (GB/UK)

Approved - usually available as a prescription only medicine to be authorised by suitably qualified person (POM-VPS)

EU Regulatory approval status

Approved

Chemical structure

Isomerism

Epinephrine exhibits optical isomerism, specifically existing as two enantiomers: R(-)-epinephrine and S(+)-epinephrine. The molecule contains a single chiral centre at the carbon bearing the hydroxyl group adjacent to the amine (the beta-carbon), which gives rise to these two forms. The R(-)-enantiomer, also called L-epinephrine, is the naturally occurring, biologically active hormone secreted by the adrenal glands.

Chemical formula

C₉H₁₃NO₃

Canonical SMILES

CNCC(C1=CC(=C(C=C1)O)O)O

Isomeric SMILES

CNC[C@@H](C1=CC(=C(C=C1)O)O)O

International Chemical Identifier key (InChIKey)

UCTWMZQNUQWSLP-VIFPVBQESA-N

International Chemical Identifier (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

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
epinephrine	-

General status

Veterinary substance type

Medicinal drug

Other bioactivity & uses

Hormone

Substance groups

Unclassified medicinal drug; Hornone

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Antagonizes the effects of histamine, raises blood sugar, increases heart rate and contractility, and increases systolic blood pressure.

Molecular targets

[Adrenergic receptors]

CAS RN

51-43-4

Alternative/old CAS RN

51028-73-0

EC number

200-098-7

CIPAC number

US EPA chemical code

PubChem CID

5816

Therapeutic Class

Multiple therapeutic classes

ATCvet Code

QA01AD01; QB02BC09; QC01CA03; QC01CA24; QR01AA14; QR03AA01; QR03AK01; QS01EA01; QS01EA51

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

183.21

PIN (Preferred Identification Name)

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

IUPAC name

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

CAS name

Forever chemical

Other status information

Relevant Environmental Water Quality Standards

Physical state

White microcrystalline powder

Related substances & organisms

epinephrine acid tartrate

Commercial

Property

Value

Availability status

Current

Introduction & key dates

1893, clinical effects first observed; 1898, first isolated

Example manufacturers & suppliers of products using this active now or historically

Norbrook Laboratories Limited
Dechra Ltd

Example products using this active

Adrenacaine Solution for Injection
Tri-solfen Cutaneous Solution

Formulation and application details

Usually formulated as solutions for injection but also as cutaneous sprays for topical use

Commercial production

Commercial production of epinephrine involves a carefully controlled multi-step chemical synthesis designed to yield the biologically active R(-)-enantiomer. The process typically begins with a catechol precursor, such as 3,4-dihydroxybenzaldehyde, which undergoes condensation with methylamine to form an imine intermediate. This is followed by asymmetric hydrogenation, often catalysed by a rhodium complex with a chiral phosphine ligand, to produce the desired stereochemistry at the beta-carbon. The resulting compound is then subjected to oxidation and salt formation, yielding epinephrine hydrochloride. Modern innovations in manufacturing, such as fermentation-based biotechnological methods and process automation, are increasingly adopted to improve efficiency, reduce waste, and meet rising global demand.

Impact on climate of production and use

Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. Notably, if the more modern fermentation route is used for production GHG emissions are likely to be towards the lower end of the range, if not less.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

100

Moderate

Solubility - In organic solvents at 20 °C (mg l⁻¹)

Melting point (°C)

211.5

Boiling point (°C)

215

Degradation point (°C)

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

4.27 X 10^-02

Calculated

Log P

-1.37

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.28

Dissociation constant pKa) at 25 °C

8.59

Vapour pressure at 20 °C (mPa)

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Surface tension (mN m⁻¹)

Refractive Index

Environmental release

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

Manure DT₅₀ (days)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Sediment phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

Mouse

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹ dw soil)

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹ dw soil)

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Vegetative vigour ER₅₀ (g ha⁻¹)

Seedling emergence ER₅₀ (g ha⁻¹)

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Notes

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic Plants (free-floating, fonds growth, fresh) - 7 day (mg l⁻¹)

Aquatic plants (rooted, growth rate, fresh) - 14 day (mg l⁻¹)

Algae - Acute (growth rate, fresh; mg l⁻¹)

Algae - Chronic (growth rate, fresh; mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀, development (mg l⁻¹)

1.83

Crassostrea gigas Larva

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

Mouse

High

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

300

Mouse

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Mammalian dose elimination route and rate

Excreted rapidly in urine

Health issues

Specific human health issues (hazard-based)

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

No information available

Handling issues

Property

Value and interpretation

General

When heated to decomposition it will emit toxic fumes
Combustible
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H301, H311, H315, H319, H335

WHO Classification

Not listed (Not listed)

UN Number

UN2811

Waste disposal & packaging

Packaging Group II (moderate danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions

TRANSLATIONS

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English

epinephrine

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Record last updated:	16/09/2025
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242