Tyramine

Summary

Tyramine (CHEMBL11608) is a phase-3 clinical-stage small-molecule EC 3.1.1.8 (cholinesterase) inhibitor targeting TAAR1; indicated across 3 conditions including parkinson disease and orthostatic hypotension.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• Targets: 1 (TAAR1)
• Indications: 3 conditions
• Clinical trials: 4
• Chemistry: 137.18 Da · C8H11NO

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL11608
Name	Tyramine
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	5610
ChEBI	CHEBI:15760
Molecular formula	C8H11NO
Molecular weight	137.18
InChIKey	DZGWFCGJZKJUFP-UHFFFAOYSA-N

SMILES: C1=CC(=CC=C1CCN)O

IUPAC name: 4-(2-aminoethyl)phenol

ChEBI definition: A primary amino compound obtained by formal decarboxylation of the amino acid tyrosine.

Pharmacological roles (ChEBI): neurotransmitter, EC 3.1.1.8 (cholinesterase) inhibitor.

Other ChEBI roles (chemical / environmental): human metabolite, Escherichia coli metabolite, mouse metabolite.

Also known as: FEMA NO. 4215, NSC-249188, tyramine-, Systogene, Tocosine, Tyramine, Tyrosamine, Uteramine, SID11111872, SID858070, SID90341354, SID104171251

Parent form; salt/anhydrous children: CHEMBL1255790

Patent coverage: 11,602 distinct patent families (38,171 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
TAAR1	TA1 receptor	Full agonist	7.7	0%	Q96RJ0

Broader ChEMBL bioactivity targets: 16 (assay-derived). Sample: Lethal(3)malignant brain tumor-like protein 1, Lysine-specific demethylase 4E, Inositol monophosphatase 1, Alpha-2A adrenergic receptor, 5-hydroxytryptamine receptor 3A, Serotonin (5-HT) receptor, 5-hydroxytryptamine receptor 1A, Sodium-dependent noradrenaline transporter, Muscarinic acetylcholine receptor M1, 5-hydroxytryptamine receptor 2B.

Bioactivity

ChEMBL activities: 16 potent at pChembl ≥ 5 of 25 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
Q923Y9	7.52	EC50	30	nM	CHEMBL_ACT_24866676
P08482	7.3	Potency	50.1	nM	CHEMBL_ACT_4803550
Q923Y9	7.16	EC50	69	nM	CHEMBL_ACT_18042027
TAAR1	7.12	EC50	76	nM	CHEMBL_ACT_24366745
TAAR1	6.75	EC50	177.7	nM	CHEMBL_ACT_13169211
Q923Y9	6.64	EC50	228.1	nM	CHEMBL_ACT_29182694
Q923Y8	6.55	EC50	280	nM	CHEMBL_ACT_24866677
TAAR1	6.14	EC50	731	nM	CHEMBL_ACT_2558493
Q923Y8	6.07	EC50	850.2	nM	CHEMBL_ACT_29182686
TAAR1	6.05	IC50	881.8	nM	CHEMBL_ACT_13128503
TAAR1	6.03	EC50	930.1	nM	CHEMBL_ACT_29182488
TAAR1	6	EC50	990	nM	CHEMBL_ACT_24866675
P30994	5.1	Kd	7943	nM	CHEMBL_ACT_1203533
HTR1A	5.1	AC50	7884	nM	CHEMBL_ACT_25165129
P08909	5.07	Kd	8511	nM	CHEMBL_ACT_1203532
P08909	5.07	Kd	8511	nM	CHEMBL_ACT_222417

Target pathways

Aggregated over 1 target gene(s): TAAR1.

Top Reactome pathways

7 total, by targets touching each:

Pathway	Targets	Genes
Signal Transduction	1	TAAR1
Signaling by GPCR	1	TAAR1
Class A/1 (Rhodopsin-like receptors)	1	TAAR1
Amine ligand-binding receptors	1	TAAR1
GPCR downstream signalling	1	TAAR1
G alpha (s) signalling events	1	TAAR1
GPCR ligand binding	1	TAAR1

Dominant GO biological processes

GO term	Targets
G protein-coupled receptor signaling pathway	1
adenylate cyclase-activating G protein-coupled receptor signaling pathway	1
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway	1
phospholipase C-activating G protein-coupled receptor signaling pathway	1
signal transduction	1

Indications & clinical

Indications

3 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
Parkinson disease	3	MONDO:0005180	MONDO:0005180
orthostatic hypotension	1	MONDO:0005469	EFO:0005252
postural orthostatic tachycardia syndrome	1	MONDO:0011479	EFO:1000645

Clinical trials

Total trials: 4.

Phase distribution

Phase	Trials
PHASE1	3
PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00203125	PHASE3	COMPLETED	A Study to Evaluate the Effects of Tyramine in Patients Who Completed the PRESTO Study.
NCT00748059	PHASE1	COMPLETED	The Pathophysiology of Orthostatic Hypotension
NCT03694119	PHASE1	COMPLETED	Drug-drug Interaction Study of Ozanimod With Tyramine to Evaluate the Effect on Pressor Response
NCT03979820	PHASE1	TERMINATED	A Study in Healthy People to Test How Combining BI 1467335 and Tyramine Affects Blood Pressure

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

22 molecules share ≥1 primary target. Top 22 by shared-target count:

Molecule	Source	Status	Shared targets
DEXTROAMPHETAMINE	ChEMBL + PubChem	Phase 4 (approved)	TAAR1
DOPAMINE	ChEMBL + PubChem	Phase 4 (approved)	TAAR1
METHAMPHETAMINE	ChEMBL + PubChem	Phase 4 (approved)	TAAR1
PHENTERMINE	ChEMBL + PubChem	Phase 4 (approved)	TAAR1
TOLAZOLINE	ChEMBL + PubChem	Phase 4 (approved)	TAAR1
FENOLDOPAM	ChEMBL	Phase 4 (approved)	TAAR1
GUANABENZ	ChEMBL	Phase 4 (approved)	TAAR1
HYDROXYAMPHETAMINE	ChEMBL	Phase 4 (approved)	TAAR1
LEVAMFETAMINE	ChEMBL	Phase 4 (approved)	TAAR1
NAPHAZOLINE	ChEMBL	Phase 4 (approved)	TAAR1
TETRAHYDROZOLINE	ChEMBL	Phase 4 (approved)	TAAR1
SEROTONIN	ChEMBL + PubChem	Phase 3 (approved)	TAAR1
ANTAZOLINE	ChEMBL	Phase 3	TAAR1
ULOTARONT	ChEMBL	Phase 3	TAAR1
LEVMETAMFETAMINE	ChEMBL + PubChem	Phase 2 (approved)	TAAR1
AZAQUINZOLE	ChEMBL	Phase 2	TAAR1
FORMETOREX	ChEMBL	Phase 2	TAAR1
RALMITARONT	ChEMBL	Phase 2	TAAR1
Amiodarone	PubChem	Approved	TAAR1
Octopamine	PubChem	Approved	TAAR1
Pyrimethamine	PubChem	Approved	TAAR1
Trimethoprim	PubChem	Approved	TAAR1