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
Structure for Tyramine (DB08841)
- Weight
- Average: 137.179
Monoisotopic: 137.084063979 - Chemical Formula
- C8H11NO
- Synonyms
- Not Available
- External IDs
- FEMA NO. 4215
- NSC-249188
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol Tyramine may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Aceclofenac is combined with Tyramine. Acemetacin The risk or severity of hypertension can be increased when Tyramine is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Tyramine. Aclidinium The risk or severity of Tachycardia can be increased when Tyramine is combined with Aclidinium. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Tyramine hydrochloride Z5KDH3H147 60-19-5 RNISDHSYKZAWOK-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
- External Links
- Human Metabolome Database
- HMDB0000306
- KEGG Compound
- C00483
- PubChem Compound
- 5610
- PubChem Substance
- 310264900
- ChemSpider
- 5408
- BindingDB
- 29135
- 10958
- ChEBI
- 15760
- ChEMBL
- CHEMBL11608
- ZINC
- ZINC000000002233
- PDBe Ligand
- AEF
- Wikipedia
- Tyramine
- PDB Entries
- 3bra / 4n7c / 5ff9 / 8eek
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 1 Completed Not Available Healthy Subjects (HS) 1 1 Completed Basic Science Healthy Subjects (HS) 1 1 Completed Screening Disorders of the Autonomic Nervous System / Dopamine Beta Hydroxylase Deficiency / Orthostatic Hypotension / Orthostatic Intolerance 1 1 Terminated Treatment Healthy Subjects (HS) 1
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
Property Value Source Water Solubility 5.72 mg/mL ALOGPS logP -0.14 ALOGPS logP 0.68 Chemaxon logS -1.4 ALOGPS pKa (Strongest Acidic) 10.41 Chemaxon pKa (Strongest Basic) 9.66 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 46.25 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 41.27 m3·mol-1 Chemaxon Polarizability 15.33 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 130.8671769 predictedDarkChem Lite v0.1.0 [M-H]- 130.9307769 predictedDarkChem Lite v0.1.0 [M-H]- 130.7990769 predictedDarkChem Lite v0.1.0 [M-H]- 130.9840769 predictedDarkChem Lite v0.1.0 [M-H]- 125.54112 predictedDeepCCS 1.0 (2019) [M+H]+ 131.7868769 predictedDarkChem Lite v0.1.0 [M+H]+ 131.5474769 predictedDarkChem Lite v0.1.0 [M+H]+ 131.6932769 predictedDarkChem Lite v0.1.0 [M+H]+ 131.6932769 predictedDarkChem Lite v0.1.0 [M+H]+ 129.3194 predictedDeepCCS 1.0 (2019) [M+Na]+ 131.0676769 predictedDarkChem Lite v0.1.0 [M+Na]+ 131.0264769 predictedDarkChem Lite v0.1.0 [M+Na]+ 131.0253769 predictedDarkChem Lite v0.1.0 [M+Na]+ 130.9019769 predictedDarkChem Lite v0.1.0 [M+Na]+ 138.19585 predictedDeepCCS 1.0 (2019)
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
- 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. [Article]
Drug created at February 27, 2013 21:20 / Updated at June 12, 2020 16:52