Compound
(R)-adrenaline
An organic cation that is the conjugate acid of (R)-adrenaline, obtained by protonation of the amino group; major species at pH 7.3.
Definition from ChEBI (CHEBI:71406), read 2026-09-23. CC BY 4.0.
Structure
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- Class
- Organic compound, cation
- Formula
- C9H14NO3
- Mass
- 184.215 g/mol
- Charge
- +1
- InChIKey
- UCTWMZQNUQWSLP-VIFPVBQESA-O
- SMILES
- C[NH2+]C[C@H](O)c1ccc(O)c(O)c1
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
8 entities
8 entities reached.
0 reported hops8 assembled from the scaffold
- MAOAProteinUNIPROT:P21397metabolized byInferred only36 paths36 endpoints
- SULT1A3ProteinUNIPROT:P0DMM9metabolized byInferred only15 paths15 endpoints
- MAOBProteinUNIPROT:P27338metabolized byInferred only13 paths13 endpoints
- SULT1A4ProteinUNIPROT:P0DMN0metabolized byInferred only8 paths8 endpoints
- SLC22A2ProteinUNIPROT:O15244transported byInferred only5 paths5 endpoints
- SLC22A3ProteinUNIPROT:O75751transported byInferred only4 paths4 endpoints
- SLC22A1ProteinUNIPROT:O15245transported byInferred only3 paths3 endpoints
- SLC29A4ProteinUNIPROT:Q7RTT9transported byInferred only1 path1 endpoint
What the reference databases state
Statements
12 statements
12 statements · 1 reference database · Subject: (R)-adrenaline · Sources: Rhea
- (R)-adrenaline is converted to (R)-adrenaline 4'-O-sulfateCompoundRhea RHEA:83343Inferred only
- (R)-metanephrine is converted to (R)-adrenalineCompoundRhea RHEA:72251Inferred only
- (R)-adrenaline is converted to (R)-metanephrineCompoundRhea RHEA:72251Inferred only
- (R)-noradrenaline is converted to (R)-adrenalineCompoundRhea RHEA:25269Inferred only
- (R)-adrenaline is metabolised by MAOAProteinRhea RHEA:51168Inferred only
- (R)-adrenaline is metabolised by MAOBProteinRhea RHEA:51168Inferred only
- (R)-adrenaline is metabolised by SULT1A3ProteinRhea RHEA:83343Inferred only
- (R)-adrenaline is metabolised by SULT1A4ProteinRhea RHEA:83343Inferred only
- (R)-adrenaline is transported by SLC22A1ProteinRhea RHEA:73875Inferred only
- (R)-adrenaline is transported by SLC22A2ProteinRhea RHEA:73875Inferred only
- (R)-adrenaline is transported by SLC22A3ProteinRhea RHEA:73875Inferred only
- (R)-adrenaline is transported by SLC29A4ProteinRhea RHEA:73875Inferred only
Reactions
6 reactions
(R)-noradrenaline+S-adenosyl-L-methionine(R)-adrenaline+S-adenosyl-L-homocysteine+hydron
Catalysed by PNMT
Reaction pageLeft to rightBalanced
Rhea RHEA:25269CC BY 4.0Reference data
(R)-adrenaline+dioxygen+water(R)-3,4-dihydroxymandelaldehyde+methylamine+hydrogen peroxide
Reaction pageDirection not assertedBalanced
Rhea RHEA:51168CC BY 4.0Reference data
(R)-adrenaline+S-adenosyl-L-methionine(R)-metanephrine+S-adenosyl-L-homocysteine+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:72251CC BY 4.0Reference data
(R)-adrenaline+2hydron(R)-adrenaline+2hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:73751CC BY 4.0Reference data
Transported by SLC22A2 or SLC22A1 or SLC22A3 or SLC29A4
Reaction pageDirection not assertedBalanced
Rhea RHEA:73875CC BY 4.0Reference data
(R)-adrenaline+3'-phosphoadenylyl sulfate(R)-adrenaline 4'-O-sulfate+adenosine 3',5'-bisphosphate+hydron
Catalysed by SULT1A3 or SULT1A4
Reaction pageLeft to rightBalanced
Rhea RHEA:83343CC BY 4.0Reference data
Where it reaches
2 systems, 3 regions, 6 tissues, 6 transporter routes — routes, not measurements: transporters known to carry (R)-adrenaline are expressed there, and no source reports it arriving.
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Other names
4 names
Resolves to: (R)-adrenaline
- Also called
- (R)-adrenaline cationL-epinephrine cationL-epinephrine(1+)
- Systematic name
- (2R)-2-(3,4-dihydroxyphenyl)-2-hydroxy-N-methylethanaminium