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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:41 UTC
HMDB IDHMDB15639
Secondary Accession NumbersNone
Metabolite Identification
Common NameMepyramine
DescriptionMepyramine (also known as pyrilamine) is a first generation antihistamine, targeting the H1 receptor. However, it rapidly permeates the brain and so often causes drowsiness as a side effect. It is used in over-the-counter combination products for colds and menstrual symptoms.
Structure
Thumb
Synonyms
ValueSource
N',n'-dimethyl-N-(P-methoxybenzyl)-N-(2-pyridyl)ethylenediamineChEBI
N-(P-Methoxybenzyl)-n',n'-dimethyl-N-(alpha-pyridyl)ethylenediamineChEBI
N-[(4-Methoxyphenyl)methyl]-n',n'-dimethyl-N-2-pyridinyl-1,2-ethanediamineChEBI
PyranisamineChEBI
PyrilamineChEBI
N-(P-Methoxybenzyl)-n',n'-dimethyl-N-(a-pyridyl)ethylenediamineGenerator
N-(P-Methoxybenzyl)-n',n'-dimethyl-N-(α-pyridyl)ethylenediamineGenerator
Chemical FormulaC17H23N3O
Average Molecular Weight285.384
Monoisotopic Molecular Weight285.184112373
IUPAC NameN-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine
Traditional Namemepyramine
CAS Registry Number91-84-9
SMILES
COC1=CC=C(CN(CCN(C)C)C2=NC=CC=C2)C=C1
InChI Identifier
InChI=1S/C17H23N3O/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h4-11H,12-14H2,1-3H3
InChI KeyInChIKey=YECBIJXISLIIDS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylmethylamines
Alternative Parents
Substituents
  • Methoxybenzene
  • Dialkylarylamine
  • Phenylmethylamine
  • Phenol ether
  • Benzylamine
  • Anisole
  • Aminopyridine
  • Alkyl aryl ether
  • Imidolactam
  • Pyridine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antihistamines
  • Histamine H1 Antagonists
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.81e-01 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.78 mg/mLALOGPS
logP2.89ALOGPS
logP3.04ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area28.6 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity87.74 m3·mol-1ChemAxon
Polarizability32.89 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06691
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06691
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06691
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4818
KEGG Compound IDC11798
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMepyramine
NuGOwiki LinkHMDB15639
Metagene LinkHMDB15639
METLIN IDNot Available
PubChem Compound4992
PDB IDNot Available
ChEBI ID6762
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. [19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Moriyama K, Liu J, Jang Y, Chae YJ, Wang Y, Mitchell J, Grond S, Han X, Xing Y, Xie GX, Pierce Palmer P: Receptor mediation and nociceptin inhibition of bradykinin-induced plasma extravasation in the knee joint of the rat. Inflamm Res. 2009 Dec;58(12):873-80. Epub 2009 Jun 21. [19544046 ]
  2. Chhabria MT, Patel VT, Rajan KS, Brahmkshatriya PS: Design, synthesis and histamine H1-receptor antagonistic activity of some novel 4-amino-2-(substituted)-5-(substituted) aryl-6-[(substituted aryl) amino] pyrimidines. Arzneimittelforschung. 2009;59(5):243-7. [19537525 ]
  3. Mojtahedin A, Tamaddonfard E, Zanboori A: Antinociception induced by central administration of histamine in the formalin test in rats. Indian J Physiol Pharmacol. 2008 Jul-Sep;52(3):249-54. [19552055 ]
  4. Parsons ME, Ganellin CR: Histamine and its receptors. Br J Pharmacol. 2006 Jan;147 Suppl 1:S127-35. [16402096 ]
  5. Snowman AM, Snyder SH: Cetirizine: actions on neurotransmitter receptors. J Allergy Clin Immunol. 1990 Dec;86(6 Pt 2):1025-8. [1979798 ]