pyrilamine

Also known as Anthisan®, mepiramine, mepyramine maleate, pyrilamine tannate, Pyrlex®, N',N'-dimethyl-N-(p-methoxybenzyl)-N-(2-pyridyl)ethylenediamine, N-(p-methoxybenzyl)-N',N'-dimethyl-N-(alpha-pyridyl)ethylenediamine

Mepyramine, also known as pyrilamine, is a first-generation antihistamine, targeting the H1 receptor as an inverse agonist. Mepyramine rapidly permeates the brain, often causing drowsiness.

Chemical data

Formula: C17H23N3O
Molecular weight: 285.4 g/mol
IUPAC name: N'-[(4-methoxyphenyl)methyl]-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine
SMILES: CN(C)CCN(CC1=CC=C(C=C1)OC)C2=CC=CC=N2
InChIKey: YECBIJXISLIIDS-UHFFFAOYSA-N
XLogP: 3.3
Polar surface area: 28.6 Å²
H-bond donors: 0
H-bond acceptors: 4
Formal charge: 0

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Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1973
Admin. routes: oral, topical
Indications: Pruritus, allergic disease

via ChEMBL · EBI

Research

2,541 papers

Physical and biological properties of pyrilamine.Journal of pharmaceutical sciences · 1983
[Research progress of pyrilamine-sensitive H~+/OC antiporter].Yao xue xue bao = Acta pharmaceutica Sinica · 2016
Pyrilamine-sensitive proton-coupled organic cation (H(+)/OC) antiporter for brain-specific drug delivery.Journal of controlled release : official journal of the Controlled Release Society · 2017
Involvement of proton-coupled SLC49A4-mediated transport in the export of lysosomally trapped pyrilamine.Drug metabolism and disposition: the biological fate of chemicals · 2023
Chronic feeding study of pyrilamine in Fischer 344 rats.Fundamental and applied toxicology : official journal of the Society of Toxicology · 1995

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 285.184112
Has use: medication

Show 5 more facts

chemical formula: C₁₇H₂₃N₃O
canonical SMILES: CN(C)CCN(CC1=CC=C(C=C1)OC)C2=CC=CC=N2
subject has role: hypnotic
physically interacts with: Histamine receptor H1
Commons category: Mepyramine

Sources (3)

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Encyclopedic overview

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References

Mepyramine, also known as pyrilamine, is a first-generation antihistamine, targeting the H1 receptor as an inverse agonist. Mepyramine rapidly permeates the brain, often causing drowsiness. It is often sold as a maleate salt, pyrilamine maleate.

The medication has negligible anticholinergic activity, with 130,000-fold selectivity for the histamine H1 receptor over the muscarinic acetylcholine receptors (for comparison, diphenhydramine had 20-fold selectivity for the H1 receptor).

Excerpted from Wikipedia’s “pyrilamine” article, available under the CC BY-SA 4.0 licence.

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