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pyrilamine maleate
1,2-ethanediamine, N1-[(4-methoxyphenyl)methyl]-N2,N2-dimethyl-N1-2-pyridinyl-, (2Z)-2-butenedioate (1:1)

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Name:(Z)-but-2-enedioicacid;N'-[(4-methoxyphenyl)methyl]-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine
CAS Number: 59-33-6Picture of molecule3D/inchi
Other(deleted CASRN):5572-06-5
FDA UNII: R35D29L3ZA
MDL:MFCD00069333
Molecular Weight:401.46319000
Formula:C21 H27 N3 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:white crystals or powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 423.80 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.000000 mmHg @ 25.00 °C. (est)
Flash Point: 410.00 °F. TCC ( 210.10 °C. ) (est)
logP (o/w): 2.751 (est)
Soluble in:
 water, 119.7 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
American International Chemical, LLC.
Pyrilamine Maleate
BOC Sciences
For experimental / research use only.
Pyrilamine maleate salt 95%
Odor: characteristic
Use: Pyrilamine maleate salt is a first generation antihistamine and binds with high affinity to G(q/11) protein. It is commonly utilized as a radioligand binding assay for the H1 receptor. It also has anticholinergic properties.
Penta International
PYRILAMINE MALEATE USP/NF
Sigma-Aldrich: Sigma
For experimental / research use only.
Pyrilamine maleate salt
TCI AMERICA
For experimental / research use only.
Pyrilamine Maleate >98.0%(HPLC)(T)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-child LDLo 42 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA GASTROINTESTINAL: NAUSEA OR VOMITING
Lancet. Vol. 2, Pg. 809, 1952.

intravenous-guinea pig LD50 24400 ug/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 113, Pg. 313, 1958.

intraperitoneal-mouse LD50 100 mg/kg
Planta Medica. Vol. 42, Pg. 75, 1981.

intravenous-mouse LD50 23 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 47, 1965.

oral-mouse LD50 220 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 47, 1965.

oral-rat LD50 513 mg/kg
Toxicology and Applied Pharmacology. Vol. 1, Pg. 42, 1959.

Dermal Toxicity:
subcutaneous-guinea pig LD50 44 mg/kg
Annales Pharmaceutiques Francaises. Vol. 20, Pg. 463, 1962.

subcutaneous-mouse LD50 141 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 14, Pg. 940, 1964.

subcutaneous-rat LDLo 150 mg/kg
BEHAVIORAL: TREMOR
Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 144, Pg. 887, 1950.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
pharmaceuticals / chemical synthisis
Recommendation for pyrilamine maleate usage levels up to:
 not for fragrance use.
 
Recommendation for pyrilamine maleate flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):59-33-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5284451
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(Z)-but-2-enedioicacid;N'-[(4-methoxyphenyl)methyl]-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine
Chemidplus:0000059336
EPA/NOAA CAMEO:hazardous materials
RTECS:UT1225000 for cas# 59-33-6
 
References:
 (Z)-but-2-enedioicacid;N'-[(4-methoxyphenyl)methyl]-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5284451
Pubchem (sid):134972293
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
KEGG (GenomeNet):D05660
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2933.39.4100
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 anisopyradamine
 anthisan
(Z)-but-2-enedioicacid;N'-[(4-methoxyphenyl)methyl]-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine
 diaminide maleate
2-((2-(dimethylamino)ethyl)(p-methoxybenzyl)amino)-pyridine maleate
2-[[2-(dimethylamino)ethyl](p-methoxybenzyl)amino]pyridine bimaleate
2-[[2-(dimethylamino)ethyl](p-methoxybenzyl)amino]pyridine maleate
[2-(dimethylamino)ethyl][(4-methoxyphenyl)methyl]-2-pyridylamine, (2Z)but-2-enedioic acid
 dorantamin maleate
 enrumay
1,2-ethanediamine, N-[ (4-methoxyphenyl)methyl]-N', N'-dimethyl-N-2-pyridinyl-, (Z)-2-butenedioate (1:1)
1,2-ethanediamine, N1-[(4-methoxyphenyl)methyl]-N2,N2-dimethyl-N1-2-pyridinyl-, (2Z)-2-butenedioate (1:1)
 histatex
 histavet-P
 mepiramine maleate
 mepyramine hydrogen maleinate
 mepyramine maleate
N-p-methoxybenzyl-N',N'-dimethyl-N-a-pyridylethylenediamine maleate
N-(p-methoxybenzyl)-N, N'-dimethyl-N-2-pyridyl-1,2-ethanediamine, maleic acid salt
N-(4-methoxybenzyl)-N',N'-dimethyl-N-(2-pyridinyl)-1,2-ethanediamine (2Z)-2-butenedioate (1:1)
N-(4-methoxybenzyl)-N',N'-dimethyl-N-(pyridin-2-yl)ethane-1,2-diamine (2Z)-but-2-enedioate (1:1)
N-(4-methoxybenzyl)-N',N'-dimethyl-N-pyridin-2-ylethane-1,2-diamine (2Z)-but-2-enedioate
N-(4-methoxyphenyl)methyl-N',N'-dimethyl-N-(2-pyridinyl)-1,2-ethanediamine maleate salt
N-[(4-methoxyphenyl)methyl]-N',N'-dimethyl-N-2-pyridinyl-1,2-ethanediamine (2Z)-2-butenedioate (1:1)
 paraminyl maleate
 pyra maleate
 pyramal maleate
 pyranilamine maleate
 pyranisamine maleate
 pyridine, 2-((2-(dimethylamino)ethyl)(p-methoxybenzyl)amino)-, maleate (1:1)
 pyridine, 2-[[2- (dimethylamino)ethyl](p-methoxybenzyl)amino]-, maleate (1:1)
 stangen maleate
 statomin maleate
 thylogen
 

Articles:

PubMed:Histamine in the locus coeruleus promotes descending noradrenergic inhibition of neuropathic hypersensitivity.
PubMed:Lymphatic diamine oxidase secretion stimulated by fat absorption is linked with histamine release.
PubMed:Evaluation of In Vitro Uterotonic Activities of Fruit Extracts of Ficus asperifolia in Rats.
PubMed:Antihistaminic drugs modify casein-induced inflammation in the rat.
PubMed:Prevalence and impact of primary dysmenorrhea among Mexican high school students.
PubMed:Effects of inhaled monoethanolamine on bronchoconstriction.
PubMed:Patterns of prescription and self-medication for treating primary dysmenorrhea in a Mexican population.
PubMed:Stimulation of brain mast cells by compound 48/80, a histamine liberator, evokes renin and vasopressin release in dogs.
PubMed:Minimal role for H1 and H2 histamine receptors in cutaneous thermal hyperemia to local heating in humans.
PubMed:Relaxant effects of the neutral extract of the leaves of Bidens pilosa Linn on isolated rat vascular smooth muscle.
PubMed:Involvement of histamine H1 and H2 receptors in the regulation of STAT-1 phosphorylation: inverse agonism exhibited by the receptor antagonists.
PubMed:H1 but not H2 histamine receptor activation contributes to the rise in skin blood flow during whole body heating in humans.
PubMed:Degranulation of mast cells located in median eminence in response to compound 48/80 evokes adrenocortical secretion via histamine and CRF in dogs.
PubMed:Interactions of eosinophil granule proteins with skin: limits of detection, persistence, and vasopermeabilization.
PubMed:Regulation by prostaglandin E2 and histamine of angiogenesis in inflammatory granulation tissue.
PubMed:Non-adrenergic non-cholinergic excitatory innervation in the airways: role of neurokinin-2 receptors.
PubMed:Neurochemical regulation of cough response to capsaicin in guinea-pigs.
PubMed:NTP Hepatotoxicity Studies of the Liver Carcinogen Methapyrilene Hydrochloride (CAS No. 135-23-9) Administered in Feed to Male F344/N Rats.
PubMed:Enhancement by histamine of vascular endothelial growth factor production in granulation tissue via H(2) receptors.
PubMed:Histamine induced decrease of lecithin levels in broncho-alveolar lavage fluid of rats is mediated by H2 receptor.
PubMed:Effect of pyloric blockade and infusion of histamine or pentagastrin on gastric secretion in horses.
PubMed:Histamine-induced gastric acid secretion in horses.
PubMed:Evidence for hypernociception induction following histamine H1 receptor activation in rodents.
PubMed:Effect of antioxidants, anti-inflammatory drugs, and histamine antagonists on sparfloxacin-induced phototoxicity in mice.
PubMed:Chronic feeding study of pyrilamine in Fischer 344 rats.
PubMed:N(+)-glucuronidation of aliphatic tertiary amines, a general phenomenon in the metabolism of H1-antihistamines in humans.
PubMed:The acetylcholine-induced flare response in evaluation of small fiber dysfunction.
PubMed:High-performance liquid chromatography of the antihistamine pyrilamine and its N-oxide using electrochemical detection.
PubMed:Uterotropic actions of relaxin in prepubertal gilts.
PubMed:Pharmacologic modulation of vascular permeability in ocular allergy in the rat.
PubMed:Association of fever with late-onset pulmonary hypersensitivity responses in the guinea pig.
PubMed:Formation of ovarian follicular cysts and corpora lutea after treatment with antihistamine or indomethacin in prepubertal gilts.
PubMed:The probable role of histamine in the rostral hypothalamus on the prolactin and luteinizing hormone release induced by estrogen in conscious spayed rats.
PubMed:Adrenergic and histaminergic neural interactions in dog paws.
PubMed:Effect of histamine on proliferation of normal human adult lung fibroblasts.
PubMed:Analysis of some dosage forms containing pyridine derivatives using a cyclodextrin bonded stationary phase in HPLC.
PubMed:Metabolism of pyrilamine maleate in Fischer 344 rats, Part I: Activity excretion profiles.
PubMed:The metabolism and elimination of pyrilamine maleate in the rat.
PubMed:Microbial transformation of the antihistamine pyrilamine maleate. Formation of potential mammalian metabolites.
PubMed:H1 action of histamine on aldosterone and cortisol secretion by perfused dog adrenal.
PubMed:Liquid chromatographic determination of organic nitrogenous bases in dosage forms: a progress report.
PubMed:Unusual effects of histamine antagonists on canine nasal blood vessels.
PubMed:Some respiratory and enteric diseases of cattle: an update.
PubMed:PAF-acether-induced plasma exudation in rat skin is independent of platelets and neutrophils.
PubMed:Trace analysis of the antihistamines methapyrilene hydrochloride, pyrilamine maleate and triprolidine hydrochloride monohydrate in animal feed, human urine and wastewater by high-performance liquid chromatography and gas chromatography with nitrogen-phosphorus detection.
PubMed:Chronic toxicity tests of pyrilamine maleate and methapyrilene hydrochloride in F344 rats.
PubMed:Bioassays of smooth muscle contracting agents in cotton mill dust and bract extracts: arachidonic acid metabolites as possible mediators of the acute byssinotic reaction.
PubMed:Inhibition of bone resorption in tissue culture by H1-receptor antagonists.
PubMed:Measurement of canine gastric vascular permeability to plasma proteins in the normal and protein-losing states.
PubMed:Pharmacological studies of sensitized canine pulmonary blood vessels.
PubMed:GLC analysis of menthol, phenol, benzocaine, and pyrilamine maleate in aerosol spray lotion.
PubMed:Characterization of DNA repair elicited by carcinogens and drugs in the hepatocyte primary culture/DNA repair test.
PubMed:High-pressure liquid chromatographic determination of methscopolamine nitrate, phenylpropanolamine hydrochloride, pyrilamine maleate, and pheniramine maleate in tablets.
PubMed:Pulmonary polyamine permeability factor.
PubMed:An agent that releases basophil and mast cell histamine but blocks cyclooxygenase and lipoxygenase metabolism of arachidonic acid inhibits immunoglobulin E-mediated asthma in rhesus monkeys.
PubMed:Simultaneous GLC analysis of salicylamide, phenylpropanolamine hydrochloride, caffeine, chlorpheniramine maleate, phenylephrine hydrochloride, and pyrilamine maleate in capsule preparations.
PubMed:The induction of unscheduled DNA synthesis by antihistamines in primary hepatocyte cultures.
PubMed:Negligible potency of acetylcholine in increasing vascular permeability.
PubMed:Acute systemic anaphylaxis in adult domestic fowl: evidence for the protective role of H2-histaminergic and beta 2-adrenergic receptors.
PubMed:Potentiation by D-penicillamine and other sulfhydryl agents of the vascular response to histamine in the anaesthetized dog.
PubMed:Cutaneous vascular histamine H1 and H2 receptors in the guinea-pig: the histamine skin wheal as a cutaneous vascular model.
PubMed:Toxic encephalopathy related to antihistamine-barbiturate antiemetic medication.
PubMed:Quantitative determinations of codeine phosphate, guaifenesin, pheniramine maleate, phenylpropanolamine hydrochloride, and pyrilamine maleate in an expectorant by high-pressure liquid chromatography.
PubMed:Quantitative determination of four antihistamines in combination by high-pressure liquid chromatography.
PubMed:Metabolic studies of guinea pig basophilic leukocytes in short-term tissue culture. I. Measurement of histaminesynthesizing capacity by using an isotopic-thin layer chromatographic assay.
PubMed:Comparison of stability-indicating assay methods: ultraviolet, high pressure liquid chromatography and acid dye.
PubMed:Aggregation of antihistamines in aqueous solution: effect of counterions on self-association of pyridine derivatives.
PubMed:Comparison of the ocular effects of circulating endotoxin and immune complexes: role of vasoactive amines.
PubMed:A clinical comparison of rectal pyrilamine maleate and trimethobenzamide hydrochloride for the control of vomiting in children.
PubMed:Spectrophotometric determination of acetaminophen, phenylephrine hydrochloride, codeine phosphate, and pyrilamine maleate in tablets or powder.
PubMed:[The combination of phenylpropanolamine hydrochloride, pyrilamine maleate, pheniramine maleate in the therapy of some inflammatory and reactive processes of the main airways: electrophotoplethysmographic and clinical study].
PubMed:Suppressive effects of pyrilamine maleate and d-lysergic acid diethylamide (LSD-25) on early corneal lesions produced in vitro by Newcastle disease virus (NDV) and compound 48/80.
PubMed:Evaluation of a combination of pheniraminemaleate, pyrilamine maleate, and propanolamine hydrochloride (triaminic) as a diuretic agent.
PubMed:Pyrilamine maleate in the treatment of pruritic dermatoses.
 
Notes:
a histamine h1 antagonist. 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.
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