(+)-Fenfluramine hydrochloride
Basic information
- CAS
3239-45-0- Standard SMILES
CCN[C@@H](C)Cc1cccc(C(F)(F)F)c1.Cl- InChIKey
ZXKXJHAOUFHNAS-FVGYRXGTSA-N- Molecular formula
- C12H17ClF3N
- Average molar mass
- 267.72 g/mol
- Monoisotopic mass
- 267.1001617
Overview
Dexfenfluramine, also marketed under the name Redux, is a serotoninergic anorectic drug. It was for some years in the mid-1990s approved by the United States Food and Drug Administration for the purposes of weight loss. However, following multiple concerns about the cardiovascular side-effects of the drug, such approval was withdrawn.
Names & identifiers
- Preferred name
- (+)-Fenfluramine hydrochloride
- IUPAC
- (2S)-N-ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine;hydrochloride
Names & synonyms
DEXFENFLURAMINE HYDROCHLORIDE3239-45-0AdifaxAdipomind-Fenfluramine hydrochloride(+)-Fenfluramine hydrochlorideGlypolixDexfenfluramine HClS 5614 HClS-5614 HYDROCHLORIDEDTXSID7048871PM28L0FHNP
Show more names
(+)-(S)-N-Ethyl-alpha-methyl-m-(trifluoromethyl)phenethylamine hydrochlorideFENFLURAMINE D-FORM HYDROCHLORIDES-5614 HCLDTXCID0028797CHEBI:59730RefChem:132388Hydrochloride, Dexfenfluramine221-806-0
Database identifiers
- CAS
3239-45-0- PubChem CID
- 66264
- DTXSID
DTXSID7048871- ChEMBL
CHEMBL1887891- UNII
- PM28L0FHNP
- EC Number
- 221-806-0
Properties
Computed structural properties
- Topological polar surface area
- 12 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 203
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
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxicology
Treatment
General supportive measures for oral drug overdose should be instituted. Measures that have been used in dexfenfluramine overdose cases include aspiration of gastric contents, gastric lavage with activated charcoal, osmotic diuresis, forced acid diuresis, and careful monitoring of CNS or respiratory depression. The effectiveness of dialysis is not known. Patients should be followed closely until there is no further evidence of drug-related CNS effects. No specific therapy for dexfenfluramine overdose is known. (L1712)
Exposure RoutesWell-absorbed from the gastrointestinal tract.
Toxicity Summary
Dexfenfluramine binds to the serotonin reuptake pump. This causes inhbition of serotonin reuptake. The increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding behavior located in the hypothalamus. This suppresses the appetite for carbohydrates.
Chemistry & industry
Pharmacology
Metabolism/MetabolitesHalf Life: 17-20 hours
MeSH Pharmacological ClassificationEndogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS.
Uses & manufacturing
UsesA serotoninergic anorectic drug once used for the purposes of weight loss, but pulled out from the global market following multiple concerns about the cardiovascular side-effects of the drug. [Wikipedia]
Related reactions
0 records
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Compound notes
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