(S)-Carbinoxamine
Basic information
- CAS
5560-77-0- Standard SMILES
CN(C)CCO[C@@H](c1ccc(Cl)cc1)c1ccccn1- InChIKey
OJFSXZCBGQGRNV-INIZCTEOSA-N- Molecular formula
- C16H19ClN2O
- Average molar mass
- 290.79 g/mol
- Monoisotopic mass
- 290.1185909
Overview
(S)-carbinoxamine is the (S)- (active) enantiomer of carbinoxamine. It is an enantiomer of a (R)-carbinoxamine.
Names & identifiers
- Preferred name
- (S)-Carbinoxamine
- IUPAC
- 2-[(S)-(4-chlorophenyl)-pyridin-2-ylmethoxy]-N,N-dimethylethanamine
- English name
- Rotoxamine
- Molecular formula
- C16H19ClN2O
- Molecular weight
- 290.79
Names & synonyms
RotoxamineRotoxaminaRotoxaminum(S)-Carbinoxamine5560-77-0McN-R-73-ZCarbinoxamine, (s)-VED9E376NC(-)-2-(p-Chloro-alpha-(2-(dimethylamino)ethoxy)benzyl)pyridineCHEBI:59329DTXSID402041462-[(S)-(4-chlorophenyl)(pyridin-2-yl)methoxy]-N,N-dimethylethanamine
Show more names
2-[(S)-(4-chlorophenyl)-(2-pyridyl)methoxy]ethyl-dimethyl-amineEthanamine, 2-[(S)-(4-chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethyl-2-[(S)-(4-chlorophenyl)-pyridin-2-yl-methoxy]-N,N-dimethyl-ethanamine
rotossamina2-((S)-(4-chlorophenyl)(pyridin-2-yl)methoxy)-N,N-dimethylethanamineRefChem:1051176DTXCID40126637levocarbinoxamine(-)-carbinoxamine(S)-(-)-carbinoxamine2-[(S)-(4-chlorophenyl)-pyridin-2-ylmethoxy]-N,N-dimethylethanamine
Database identifiers
- CAS
5560-77-0- PubChem CID
- 170336
- DTXSID
DTXSID40204146- ChEMBL
CHEMBL1740361- ChEBI
CHEBI:59329- UNII
- VED9E376NC
- Nikkaji
- J760.546C
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 25.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 267
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Boiling point
- 143 · 143-144 °C(Press: 0.5 Torr)
- Density
- 1.143 · 1.143±0.06 g/cm3(Predicted)
- pka
- 8.65 · 8.65±0.28(Predicted)
- FDA UNII
- 9 E376NC · VED9E376NC
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Toxicity Summary
Carbinoxamine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding. Carbinoxamine's anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Pharmacology
Metabolism/MetabolitesHalf Life: 10 to 20 hours
Uses & manufacturing
Uses
For symptomatic relief of seasonal and perennial allergic rhinitis and vasomotor rhinitis, as well as allergic conjunctivitis caused by foods and inhaled allergens. Also for the relief of allergic reactions to blood or plasma, and the symptomatic management of mild, uncomplicated allergic skin manifestations of urticaria and angioedema.
Applications
UsesAntihistaminic.
Additional notes
DefinitionChEBI: The (S)- (active) enantiomer of carbinoxamine.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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