(+-)-Dimethindene
Basic information
- CAS
5636-83-9- Standard SMILES
CC(C1=C(CCN(C)C)Cc2ccccc21)c1ccccn1- InChIKey
MVMQESMQSYOVGV-UHFFFAOYSA-N- Molecular formula
- C20H24N2
- Average molar mass
- 292.4 g/mol
- Monoisotopic mass
- 292.19394877
Overview
Dimetindene is an indene.
Names & identifiers
- Preferred name
- (+-)-Dimethindene
- IUPAC
- N,N-dimethyl-2-[3-(1-pyridin-2-ylethyl)-1H-inden-2-yl]ethanamine
- English name
- DIMETHINDENE
- Molecular formula
- C20H24N2
- Molecular weight
- 292.42
Names & synonyms
DIMETHINDENEDimetindene5636-83-9DimethpyrindeneForhistalDimetindenoDimetindenumFeniallergN,N-dimethyl-2-[3-(1-pyridin-2-ylethyl)-1H-inden-2-yl]ethanamine2-(1-(2-(2-Dimethylaminoethyl)inden-3-yl)ethyl)pyridinePyridine, 2-(1-(2-(2-(dimethylamino)ethyl)inden-3-yl)ethyl)-661FH77Z3P
Show more names
Z2001TritenZ 2001Z-2001demethindene
1H-Indene-2-ethanamine, N,N-dimethyl-3-(1-(2-pyridinyl)ethyl)-DTXSID90229421H-Indene-2-ethanamine, N,N-dimethyl-3-[1-(2-pyridinyl)ethyl]-dimethyl(2-{3-[1-(pyridin-2-yl)ethyl]-1H-inden-2-yl}ethyl)amine2-(1-(2-(2-(DIMETHYLAMINO)ETHYL)INDEN-3-YL)ETHYL)PYRIDINEN,N-DIMETHYL-3-(1-(2-PYRIDINYL)ETHYL)-1H-INDENE-2-ETHANAMINEdimethyl(2-(3-(1-(pyridin-2-yl)ethyl)-1H-inden-2-yl)ethyl)amineN,N-dimethyl-2-(3-(1-pyridin-2-ylethyl)-1H-inden-2-yl)ethanamine
Database identifiers
- CAS
5636-83-9- PubChem CID
- 21855
- DTXSID
DTXSID9022942- ChEMBL
CHEMBL22108- ChEBI
CHEBI:135222- UNII
- 661FH77Z3P
- EC Number
- 227-083-8
- Nikkaji
- J8.041A
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 16.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 5
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 399
Experimental & physicochemical properties
DrugsPharmaceuticals
LogP2.7
Human DrugsPharmaceuticals
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 50 · 50 - 53°C
- Boiling point
- 424.35 °C · 424.35°C (rough estimate)
- Density
- 1.0073 · 1.0073 (rough estimate)
- refractive index
- 1.564 · 1.5640 (estimate)
- storage temp.
- Refrigerator, under inert atmosphere
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 9.58 · 9.58±0.28(Predicted)
- color
- Pale Brown to Light Brown
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Chemistry & industry
Pharmacology
ATC Code
R06AB03
R - Respiratory system
D - Dermatologicals
QR - Respiratory system
QD - Dermatologicals
Pharmacodynamics
Dimethindene occurs as a racemic mixture. The (S)-(+)-dimethindene is a potent M2-selective muscarinic receptor antagonist (with lower affinity for M1, M3, and M4 muscarinic receptors). The (R)-(-)-enantiomer is the eutomer (responsible for bioactivity) for histamine H1 receptor binding.
Mechanism of ActionDimethindene is a selective histamine H1 antagonist and binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
MeSH Pharmacological Classification
Agents, usually topical, that relieve itching (pruritus).
Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.
Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)
Cellular LocationsMembrane
Metabolite PathwaysDimetindene H1-Antihistamine Action
Uses & manufacturing
Uses
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Compound notes
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