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Record Information
Version3.6
Creation Date2006-08-24 14:25:57 UTC
Update Date2015-03-09 22:57:21 UTC
HMDB IDHMDB04825
Secondary Accession NumbersNone
Metabolite Identification
Common Namep-Octopamine
Descriptionp-Octopamine is an amine in traces quantities in plasma and cerebrospinal fluid in humans with septic encephalopathy (PMID 15932098 ).
Structure
Thumb
Synonyms
  1. (RS)-Octopamine
  2. 1-(p-Hydroxyphenyl)-2-aminoethanol
  3. 2-Amino-1-(4-hydroxyphenyl)ethanol
  4. 4-Hydroxyphenethanolamine
  5. 4-[2-Amino-1-hydroxyethyl]phenol
  6. Analet
  7. DL-Octopamine
  8. ND 50
  9. Norden
  10. Norphen
  11. Norsympathol
  12. Norsympatol
  13. Norsynephrine
  14. Norton
  15. Octopamine
  16. p-Hydroxyphenylethanolamine
  17. Racemic octopamine
Chemical FormulaC8H11NO2
Average Molecular Weight153.1784
Monoisotopic Molecular Weight153.078978601
IUPAC Name4-[(1R)-2-amino-1-hydroxyethyl]phenol
Traditional Namenorden
CAS Registry Number104-14-3
SMILES
NC[C@H](O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2/t8-/m0/s1
InChI KeyQHGUCRYDKWKLMG-QMMMGPOBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenols and derivatives. These are compounds containing a phenol moiety, which is a benzene bearing a hydroxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentPhenols and derivatives
Alternative Parents
Substituents
  • Aralkylamine
  • Phenol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.90SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility17.2 mg/mLALOGPS
logP-0.94ALOGPS
logP-0.32ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)9.64ChemAxon
pKa (Strongest Basic)8.98ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.48 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.47 m3·mol-1ChemAxon
Polarizability16.13 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0026 +/- 0.0014 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.00075 +/- 0.0005 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.024 +/- 0.0030 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.00820 (0.00-0.0168) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00036 +/- 0.000065 uMAdult (>18 years old)BothHypertension details
BloodDetected and Quantified0.0026 +/- 0.0024 uMAdult (>18 years old)BothCirrhosis details
Associated Disorders and Diseases
Disease References
Cirrhosis
  1. Yonekura T, Kamata S, Wasa M, Okada A, Yamatodani A, Watanabe T, Wada H: Simultaneous determination of plasma phenethylamine, phenylethanolamine, tyramine and octopamine by high-performance liquid chromatography using derivatization with fluorescamine. J Chromatogr. 1988 Jun 3;427(2):320-5. [3137238 ]
Hypertension
  1. Andrew R, Best SA, Watson DG, Midgley JM, Reid JL, Squire IB: Analysis of biogenic amines in plasma of hypertensive patients and a control group. Neurochem Res. 1993 Nov;18(11):1179-82. [8255371 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB010583
KNApSAcK IDC00001425
Chemspider ID389242
KEGG Compound IDC04227
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNorden
NuGOwiki LinkHMDB04825
Metagene LinkHMDB04825
METLIN ID7087
PubChem Compound440266
PDB IDOTR
ChEBI ID44715
References
Synthesis ReferenceHinsberg, O. Nucleus-substituted hydroxyl derivatives of b-amino-a-hydroxy-a-arylethanes and b-amino-a-bisarylethanes. (1923), DE 373286 CAN 18:14396 AN 1924:14396
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Andrew R, Watson DG, Best SA, Midgley JM, Wenlong H, Petty RK: The determination of hydroxydopamines and other trace amines in the urine of parkinsonian patients and normal controls. Neurochem Res. 1993 Nov;18(11):1175-7. [8255370 ]
  2. Balbi T, Fusco M, Vasapollo D, Boschetto R, Cocco P, Leon A, Farruggio A: The presence of trace amines in postmortem cerebrospinal fluid in humans. J Forensic Sci. 2005 May;50(3):630-2. [15932098 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1