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Details

Stereochemistry ACHIRAL
Molecular Formula C17H23N3O
Molecular Weight 285.384
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRILAMINE

SMILES

COC1=CC=C(CN(CCN(C)C)C2=CC=CC=N2)C=C1

InChI

InChIKey=YECBIJXISLIIDS-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C17H23N3O
Molecular Weight 285.384
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Pyrilamine (also known as Mepyramine) 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. Mepyramine is a histamine H1 receptor inverse agonist. It binds to a G protein-coupled form of the receptor and promotes a G protein-coupled inactive state of the H1 receptor that interferes with the Gq/11-mediated signaling. Mepyramine competes with histamine for binding at H1-receptor sites on the effector cell surface, resulting in suppression of histaminic edema, flare, and pruritus. The sedative properties of Mepyramine occur at the subcortical level of the CNS. It has mild hypnotic properties and some local anesthetic action and is used for allergies (including skin eruptions) both parenterally and locally. It is a common ingredient of cold remedies.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.8 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phenylephrine/ pyrilamine
Primary
MIDOL PMS
Primary
Phenylephrine/ pyrilamine
PubMed

PubMed

TitleDatePubMed
Dose-dependent inhibition of the CYP2D6 catalyzed oxidation of sparteine by mepyramine in healthy volunteers.
2001 Dec
Effects of histamine on phosphoinositide metabolism in chick cerebral cortex.
2001 Jul-Aug
Histamine H1 receptor activation stimulates mitogenesis in human astrocytoma U373 MG cells.
2001 Nov
Preclinical comparison of ebastine and other second generation H1-antihistamines.
2001 Oct
Antiallergic anti-inflammatory effects of H1-antihistamines in humans.
2002
Histochemical and biochemical studies on the secretory mechanisms of some glands of guinea-pigs treated with histamine.
2002
Topically applied aspirin decreases histamine-induced wheal and flare reactions in normal and SLS-inflamed skin, but does not decrease itch. A randomized, double-blind and placebo-controlled human study.
2002
Characterisation of the calcium responses to histamine in capsaicin-sensitive and capsaicin-insensitive sensory neurones.
2002
Antihistamine antinociception is mediated by Gi-protein activation.
2002
Impact of soil movement on carbon sequestration in agricultural ecosystems.
2002
The initial inositol 1,4,5-trisphosphate response induced by histamine is strongly amplified by Ca(2+) release from internal stores in smooth muscle.
2002 Apr
Elevated nasal mucosal G protein levels and histamine receptor affinity in a guinea pig model of nasal hyperresponsiveness.
2002 Apr
Mouse mammary epithelial cells bear histamine receptors.
2002 Apr
Insulin-induced up-regulation of histamine H1-receptors.
2002 Apr
Contractile response of horse deep dorsal penile vein to histamine.
2002 Apr
Stimulation of protein kinase B and p70 S6 kinase by the histamine H1 receptor in DDT1MF-2 smooth muscle cells.
2002 Apr
Effects of histidine, a precursor of histamine, on pentylenetetrazole-induced seizures in rats.
2002 Apr
Neuropharmacological profile of a novel potential atypical antipsychotic drug Y-931 (8-fluoro-12-(4-methylpiperazin-1-yl)- 6H-[1]benzothieno[2,3-b][1,5] benzodiazepine maleate).
2002 Apr
GBR compounds and mepyramines as cocaine abuse therapeutics: chemometric studies on selectivity using grid independent descriptors (GRIND).
2002 Apr 11
The control effect of histamine on body temperature and respiratory function in IgE-dependent systemic anaphylaxis.
2002 Aug
Effects of histamine on the contractile and electrical activity in isolated lymphatic vessels of the guinea-pig mesentery.
2002 Aug
Functional analysis of histamine receptor subtypes involved in endothelium-mediated relaxation of the human uterine artery.
2002 Aug
Accelerated clearance of Escherichia coli in experimental peritonitis of histamine-deficient mice.
2002 Aug 15
Yawning/cortical activation induced by microinjection of histamine into the paraventricular nucleus of the rat.
2002 Aug 21
Modulation of formalin-induced behaviors and edema by local and systemic administration of dextromethorphan, memantine and ketamine.
2002 Aug 23
Biochemical characterization of desloratadine, a potent antagonist of the human histamine H(1) receptor.
2002 Aug 9
Role of mast cells in the development of pancreatitis-induced multiple organ dysfunction.
2002 Feb
Histamine-induced IL-6 and IL-8 production are differentially modulated by IFN-gamma and IL-4 in human keratinocytes.
2002 Jan
Effects of brain histamine on memory deficit induced by nucleus basalis-lesion in rats.
2002 Jan
A novel phenylaminotetralin radioligand reveals a subpopulation of histamine H(1) receptors.
2002 Jul
Antinociceptive and smooth muscle contracting activities of the methanolic extract of Cassia tora leaf.
2002 Jul
The antianaphylactic effects of Crinum glaucum aqueous extract.
2002 Jul
Suppression of spontaneous scratching in hairless rats by sedatives but not by antipruritics.
2002 Jul-Aug
Modulation of the discriminative stimulus effects of cocaine and methamphetamine by the histaminergic system.
2002 Jun
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding.
2002 Jun
Role of Rho-associated protein kinase and histamine in lysophosphatidic acid-induced airway hyperresponsiveness in guinea pigs.
2002 Mar
Predicting the risk of Lyme disease: habitat suitability for Ixodes scapularis in the north central United States.
2002 Mar
The recovery of the neurally evoked secretory response of rat colonic mucosa after irradiation is independent of mast cells.
2002 Mar
Effects of the NMDA antagonist MK-801 on radial maze performance in histidine-deficient rats.
2002 Mar 22
Histamine excites GABAergic cells in the rat substantia nigra and ventral tegmental area in vitro.
2002 Mar 8
LPS-induced platelet response and rapid shock in mice: contribution of O-antigen region of LPS and involvement of the lectin pathway of the complement system.
2002 Nov 1
Investigation on the influx transport mechanism of pentazocine at the blood-brain barrier in rats using the carotid injection technique.
2002 Oct
Enhancement of neutrophil infiltration in histidine decarboxylase-deficient mice.
2002 Oct
Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells.
2002 Oct
Effects of histamine and opioid systems on memory retention of passive avoidance learning in rats.
2002 Oct 4
Ligands for histamine H(3) receptors modulate cell proliferation and migration in rat oxyntic mucosa.
2002 Sep
Cosensitivity of vagal mucosal afferents to histamine and 5-HT in the rat jejunum.
2002 Sep
Tryptase activates the mitogen-activated protein kinase/activator protein-1 pathway in human peripheral blood eosinophils, causing cytokine production and release.
2002 Sep 1
Effects of NMDA antagonist MK-801 on radial maze performance in Zucker rats.
2002 Sep 20
Mediators of adenosine- and ovalbumen-induced bronchoconstriction of sensitized guinea-pig isolated airways.
2002 Sep 6
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Allergic Rhinitis phenylephrine-pyrilamine 25 mg-60 mg oral tablet: 1 or 2 tablets orally every 12 hours as needed. phenylephrine-pyrilamine 20 mg-16 mg oral tablet, chewable, extended release: 1 or 2 tablets orally every 12 hours as needed. phenylephrine-pyrilamine 5 mg-16 mg/5 mL oral suspension, extended release: 5 to 10 mL orally every 12 hours as needed. phenylephrine-pyrilamine 9 mg-12 mg/5 mL oral suspension, extended release: 5 to 10 mL orally every 12 hours as needed, not to exceed 20 mL in 24 hours.
Route of Administration: Oral
In Vitro Use Guide
Pretreatment with the histamine H1 receptor antagonist pyrilamine (1 uM) could reduce the beta-lactoglobulin-induced response in the in vitro guinea pig mesenteric preparation
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:39:15 UTC 2019
Edited
by admin
on Tue Oct 22 00:39:15 UTC 2019
Record UNII
HPE317O9TL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRILAMINE
MI   VANDF  
Common Name English
PYRILAMINE [VANDF]
Common Name English
NSC-13136
Code English
MEPYRAMINE [INN]
Common Name English
1,2-ETHANEDIAMINE, N-((4-METHOXYPHENYL)METHYL)-N',N'-DIMETHYL-N-2-PYRIDINYL-
Systematic Name English
MEPYRAMINE [HSDB]
Common Name English
MEPYRAMINE [MART.]
Common Name English
MEPYRAMINE
HSDB   INN   MART.   WHO-DD  
INN  
Official Name English
MEPYRAMINE [WHO-DD]
Common Name English
2-((2-(DIMETHYLAMINO)ETHYL)(P-METHOXYBENZYL)AMINO)PYRIDINE
Common Name English
PYRILAMINE [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC D04AA02
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
WHO-ATC R06AC01
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
WHO-VATC QD04AA02
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
WHO-VATC QR06AC01
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
NCI_THESAURUS C29578
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
Code System Code Type Description
MERCK INDEX
M9367
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL511
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
IUPHAR
1227
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
PUBCHEM
4992
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
CAS
91-84-9
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
MESH
D011738
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
EVMPD
SUB08762MIG
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
RXCUI
9009
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY RxNorm
HSDB
91-84-9
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
ECHA (EC/EINECS)
202-102-2
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
INN
106
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
NCI_THESAURUS
C76676
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
LactMed
91-84-9
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
EPA CompTox
91-84-9
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
DRUG BANK
DB06691
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
WIKIPEDIA
MEPYRAMINE
Created by admin on Tue Oct 22 00:39:16 UTC 2019 , Edited by admin on Tue Oct 22 00:39:16 UTC 2019
PRIMARY
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