Tyramine

Identification

Generic Name
Tyramine
DrugBank Accession Number
DB08841
Background

Tyramine (4-hydroxyphenethylamine; para-tyramine, mydrial or uteramin) is a naturally occurring monoamine compound and trace amine derived from the amino acid tyrosine. Tyramine acts by inducing the release of catecholamine. An important characteristic of this product is its impediment to cross the blood-brain barrier which restrains its side effects to only nonpsychoactive peripheral sympathomimetic effects. There have been reports of hypertensive crisis in patients ingesting tyramine-rich diet in conjunction with monoamine oxidase inhibitors (MAOIs).

Type
Small Molecule
Groups
Investigational, Nutraceutical
Structure
Thumb
Weight
Average: 137.179
Monoisotopic: 137.084063979
Chemical Formula
C8H11NO
Synonyms
Not Available
External IDs
  • FEMA NO. 4215
  • NSC-249188

Pharmacology

Indication

Not Available

Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:
Machine Learning
Data Science
Drug Discovery
Accelerate your drug discovery research with our fully connected ADMET dataset
Learn more
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
With our commercial data, access important information on dangerous risks, contraindications, and adverse effects.
Learn more
Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Learn more
Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
Reduce medical errors
and improve treatment outcomes with our comprehensive & structured data on drug adverse effects.
Learn more
Reduce medical errors & improve treatment outcomes with our adverse effects data
Learn more
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbaloparatideThe risk or severity of adverse effects can be increased when Tyramine is combined with Abaloparatide.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Tyramine.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Tyramine.
AcemetacinThe risk or severity of hypertension can be increased when Tyramine is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Tyramine.
AclidiniumThe risk or severity of Tachycardia can be increased when Tyramine is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Tyramine.
AlclofenacThe risk or severity of hypertension can be increased when Tyramine is combined with Alclofenac.
AlfentanilThe risk or severity of hypertension can be increased when Alfentanil is combined with Tyramine.
AliskirenTyramine may decrease the antihypertensive activities of Aliskiren.
Interactions
Improve patient outcomes
Build effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.
Learn more
Food Interactions
Not Available

Products

Products
Comprehensive & structured drug product info
From application numbers to product codes, connect different identifiers through our commercial datasets.
Learn more
Easily connect various identifiers back to our datasets
Learn more
Product Ingredients
IngredientUNIICASInChI Key
Tyramine hydrochlorideZ5KDH3H14760-19-5RNISDHSYKZAWOK-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenethylamines. These are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Phenethylamines
Alternative Parents
2-arylethylamines / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Organopnictogen compounds / Organooxygen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 2-arylethylamine / Amine / Aralkylamine / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monoamine molecular messenger, primary amino compound, tyramines (CHEBI:15760) / Biogenic amines, Tyramine derivatives (C00483)
Affected organisms
Not Available

Chemical Identifiers

UNII
X8ZC7V0OX3
CAS number
51-67-2
InChI Key
DZGWFCGJZKJUFP-UHFFFAOYSA-N
InChI
InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
IUPAC Name
4-(2-aminoethyl)phenol
SMILES
NCCC1=CC=C(O)C=C1

References

General References
Not Available
Human Metabolome Database
HMDB0000306
KEGG Compound
C00483
PubChem Compound
5610
PubChem Substance
310264900
ChemSpider
5408
BindingDB
29135
RxNav
10958
ChEBI
15760
ChEMBL
CHEMBL11608
ZINC
ZINC000000002233
PDBe Ligand
AEF
Wikipedia
Tyramine
PDB Entries
3bra / 4n7c / 5ff9

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingScreeningAutonomic Nervous System Diseases / Dopamine Beta-Hydroxylase Deficiency / Orthostatic Hypotension / Orthostatic Intolerance1
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers1
1TerminatedTreatmentHealthy Volunteers1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.72 mg/mLALOGPS
logP-0.14ALOGPS
logP0.68ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)10.41ChemAxon
pKa (Strongest Basic)9.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.27 m3·mol-1ChemAxon
Polarizability15.33 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00di-2900000000-273503edc6a220e152b6
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00di-2900000000-80980d19fa83d4b86f91
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00di-9700000000-78d2ae48da1eee18358e
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9200000000-50c21473a7d48011358c
GC-MS Spectrum - EI-BGC-MSsplash10-00di-1900000000-9b1000a8978b57919c35
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-2900000000-273503edc6a220e152b6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-2900000000-80980d19fa83d4b86f91
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9700000000-78d2ae48da1eee18358e
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-2900000000-69892c95ab2778a208b3
Mass Spectrum (Electron Ionization)MSsplash10-053r-9500000000-6deb2b5d214f768ca448
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-0900000000-3229081a448a277191a2
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-004l-9300000000-e2fc12d41e4c40a9a296
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-004i-9000000000-92f0b12d0a64443cede8
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-001i-9200000000-50c21473a7d48011358c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-d7e9a8705227b4504c5c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-9000000000-3f02b334907c40a8315c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-0900000000-e98b3afc6fad78d45d38
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-54239e66d89de3096ca8
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0079-0902000000-f09759fc06ef461f3aa5
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-9000000000-9ffe6ee0ce68182216f7
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-0900000000-020a5decfb44fc4f97df
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-004i-0930000000-32ccc375e75dbab3195c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-00di-0900000000-51c6cc08017f1672b791
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00di-1900000000-55c25dd64462c06c5316
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0f96-9500000000-83a70aec6da00b51a6df
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-004i-9100000000-5f044e831c0d2db255fa
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-004i-9000000000-99edae3913507430bf9f
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-00di-4900000000-8944003750ac547c2024
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-0900000000-8fb72547243614622ba3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-1900000000-44bf2322645e5e00b029
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uml-9400000000-343b8fa44c724b1395c6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-7da5f9953041f5148f8e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-e62cf6efa07eeeaf1f51
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-066r-7900000000-4f78b5370ece8150a8c4
MS/MS Spectrum - , negativeLC-MS/MSsplash10-000i-0900000000-066947a256844eb6cbdc
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-00e85becc8cfc59bdb10
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-58e8539844dcdbc977cc
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-e98b6b992e1a01839bb3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00dr-0900000000-bfcd519d8cca540e68d4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-1900000000-443d60e576da797a70d1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0ffx-9500000000-55fc23fe7afe748d1bf1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-9100000000-1cccef72bfa4b910f413
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fb9-9000000000-f3e7f124fef2633f8197
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-65d023da9eb1b11298f7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-7bf85350315173cf834d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-6fee17263658cb5b3fe2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-51c6cc08017f1672b791
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-1900000000-55c25dd64462c06c5316
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0f96-9500000000-5aeadc73c34cf8e33d2c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-9100000000-5f044e831c0d2db255fa
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-9000000000-29bd478cd5164a0ab18e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-1900000000-ba59a2d5cb4492894c7d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-92a1f106f25f5368d51f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-65eeb2d3f37cd316a8c0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-9e5f9483a94586df5ca2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-3f02b334907c40a8315c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-e98b3afc6fad78d45d38
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-54239e66d89de3096ca8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-9ffe6ee0ce68182216f7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-020a5decfb44fc4f97df
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0930000000-d08de99a1ece2ad8acb6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-4900000000-8944003750ac547c2024
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-1fa26b2fc3ba88caef19
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fkc-7900000000-c3f8ea5dfbd1b3953450
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-9100000000-7746910836d04eaa190b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-9000000000-5c0325e7114236e731a5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00or-9000000000-3091e50de2c30252fac4
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0900000000-13a399246897d165177e
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
SLC22A3
Uniprot ID
O75751
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
References
  1. Grundemann D, Schechinger B, Rappold GA, Schomig E: Molecular identification of the corticosterone-sensitive extraneuronal catecholamine transporter. Nat Neurosci. 1998 Sep;1(5):349-51. [PubMed:10196521]

Drug created on February 27, 2013 21:20 / Updated on June 12, 2020 16:52