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Substance Name: Mepyramine [INN:BAN]
RN: 91-84-9
UNII: HPE317O9TL
InChIKey: YECBIJXISLIIDS-UHFFFAOYSA-N

Note

  • 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.

Molecular Formula

  • C17-H23-N3-O

Molecular Weight

  • 285.389
 

Classification Codes

  • Anti-Allergic Agents
  • Drug / Therapeutic Agent
  • Histamine Agents
  • Histamine Antagonists
  • Histamine H1 Antagonists
  • Human Data
  • Neurotransmitter Agents
  • Reproductive Effect
  • Skin / Eye Irritant
  • Sleep Aids, Pharmaceutical

Names and Synonyms

Name of Substance

  • Mepyramine [INN:BAN]
  • Pyrilamine

MeSH Heading

  • Pyrilamine

Synonyms

  • 1,2-Ethanediamine, N-((4-methoxyphenyl)methyl)-N',N'-dimethyl-N-2-pyridinyl-
  • 2-((2-(Dimethylamino)ethyl)-(p-methoxybenzyl)amino)pyridine
  • 2-((p-Methoxybenzyl)(2-(dimethylamino)ethyl)amino)pyridine
  • 5-22-08-00381 (Beilstein Handbook Reference)
  • Afko-Hist
  • Anhistabs
  • Anhistol
  • Antalergan
  • Antallergan
  • Antamine
  • Anthisan
  • BRN 0269019
  • CCRIS 4865
  • Copsamine
  • Coradon
  • Dipane
  • Dorantamin
  • EINECS 202-102-2
  • Harvamine
  • Histacap
  • Histalon
  • Histapyran
  • Histasan
  • HSDB 5187
  • Isamin
  • Kriptin
  • Maranhist
  • Mepiramina
  • Mepiramina [INN-Spanish]
  • Mepiramine
  • Mepyramin
  • Mepyramin [German]
  • Mepyramine
  • Mepyraminum
  • Mepyraminum [INN-Latin]
  • Mepyren
  • N',N'-Dimethyl-N-(p-methoxybenzyl)-N-(2-pyridyl)ethylenediamine
  • N-((4-Methoxyphenyl)methyl)-N',N'-dimethyl-N-2-pyridinyl-1,2-ethanediamine
  • N-(p-Methoxybenzyl)-N',N'-dimethyl-N-2-pyridyl-1,2-ethanediamine
  • N-(p-Methoxybenzyl)-N',N'-dimethyl-N-2-pyridylethylenediamine
  • N-(para-Methoxybenzyl)-N',N'-dimethyl-N-2-pyridylethylenediamine
  • N-p-Methoxybenzyl-N',N'-dimethyl-N-alpha-pyridylethylenediamine
  • N-para-Methoxybenzyl-N',N'-dimethyl-N-alpha-pyridylethylenediamine
  • NCI-C60651
  • Neo-Bridal
  • Neoantergan
  • NSC 13136
  • Nyscaps
  • p-Methoxybenzyl-alpha-pyridyl-dimethyl-aethylendiamin
  • p-Methoxybenzyl-alpha-pyridyl-dimethyl-aethylendiamin [German]
  • Paraminyl
  • Parmal
  • Pyra
  • Pyramal
  • Pyranisamine
  • Pyridine, 2-((2-(dimethylamino)ethyl)(p-methoxybenzyl)amino)-
  • Pyridine, 2-((p-methoxybenzyl)(2-(dimethylamino)ethyl)amino)-
  • Pyrilamine
  • RP 2786
  • Stamine
  • Stangen
  • Statomin
  • Thylogen
  • UNII-HPE317O9TL
  • Wait's green mountain antihistamine

Systematic Names

  • 1,2-Ethanediamine, N-((4-methoxyphenyl)methyl)-N',N'-dimethyl-N-2-pyridinyl-
  • 1,2-Ethanediamine, N-((4-methoxyphenyl)methyl)-N',N'-dimethyl-N-2-pyridinyl- (9CI)
  • Mepyramine
  • Pyridine, 2-((2-(dimethylamino)ethyl)(p-methoxybenzyl)amino)-
  • Pyrilamine

Superlist Name

  • Pyrilamine

Registry Numbers

CAS Registry Number

  • 91-84-9

FDA UNII

  • HPE317O9TL

Other Registry Number

  • 102206-59-7

System Generated Number

  • 0000091849

Structure Descriptors

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

InChIKey

YECBIJXISLIIDS-UHFFFAOYSA-N

Smiles

N(c1ccccn1)(Cc1ccc(OC)cc1)CCN(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo unreported 714ug/kg (0.714mg/kg) BEHAVIORAL: SLEEP

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Allergy. Vol. 19, Pg. 313, 1948.
mammal (species unspecified) LD50 subcutaneous 100mg/kg (100mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 7, Pg. 131, 1957.
mouse LD50 intraperitoneal 107mg/kg (107mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1723, 1975.
mouse LD50 intravenous 23mg/kg (23mg/kg)   Therapie. Vol. 26, Pg. 1203, 1971.
mouse LD50 oral 220mg/kg (220mg/kg)   Therapie. Vol. 26, Pg. 1203, 1971.
rat LD50 oral 950mg/kg (950mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 160, Pg. 4, 1966.
rat LD50 oral 980mg/kg (980mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 42, 1959.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 8.85 (none) 20 EXP
log P (octanol-water) 3.27 (none)   EXP
Water Solubility 245 mg/L 25 EST
Vapor Pressure 1.75E-06 mm Hg 25 EST
Henry's Law Constant 3.52E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.53E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.