LEVOFENFLURAMINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H16F3N
Molecular Weight	231.2573
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN[C@H](C)CC1=CC(=CC=C1)C(F)(F)F

InChI

InChIKey=DBGIVFWFUFKIQN-SECBINFHSA-N

InChI=1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3/t9-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C12H16F3N
Molecular Weight	231.2573
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9824670 | https://www.ncbi.nlm.nih.gov/pubmed/2886127 | https://www.ncbi.nlm.nih.gov/pubmed/11224055

LEVOFENFLURAMINE is a levorotatory enantiomer of fenfluramine, a substituted amphetamine which was formerly used to treat obesity. LEVOFENFLURAMINE has dopamine-antagonistic properties and, at high doses, increases dopamine concentrations in rat striatal dialysates. It is essentially inactive to reduce food intake in human subjects.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine receptor 60 Target ID: CHEMBL2096905 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9824670 \| https://www.ncbi.nlm.nih.gov/pubmed/2886127 \| https://www.ncbi.nlm.nih.gov/pubmed/3485052	Antagonist 2778
serotonin secretion 8 Target ID: GO:0001820 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2598057 \| https://www.ncbi.nlm.nih.gov/pubmed/3485052	Activator 1430

PubMed

Title	Date	PubMed
Neuroleptic-like effects of the l-isomer of fenfluramine on striatal dopamine release in freely moving rats.	1987 Jul 15	2886127
Differential effects of d-fenfluramine, l-fenfluramine and d-amphetamine on the microstructure of human eating behaviour.	1991 Apr	11224055
The effects of D- and L-fenfluramine (and their interactions with D-amphetamine) on psychomotor function and mood.	1996 Jun	8803646
Effects of fenfluramine and phentermine (fen-phen) on dopamine and serotonin release in rat striatum: in vivo microdialysis study in conscious animals.	1998 Nov 30	9824670
(+)-Fenfluramine and its major metabolite, (+)-norfenfluramine, are potent substrates for norepinephrine transporters.	2003 Jun	12649307
Medicine as a corporate enterprise, patient welfare centered profession, or patient welfare centered professional enterprise?	2005 Nov	22679354
Off-label promotion, on-target sales.	2008 Oct 28	18959472

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:51:58 GMT 2023` Edited by `admin` on `Fri Dec 15 18:51:58 GMT 2023`
Record UNII	953A94Y45B
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LEVOFENFLURAMINE

Official Name

English

R)-(-)-FENFLURAMINE

Common Name

English

(-)-FENFLURAMINE

Common Name

English

L-FENFLURAMINE

Common Name

English

BENZENEETHANAMINE, N-ETHYL-.ALPHA.-METHYL-3-(TRIFLUOROMETHYL)-, (.ALPHA.R)-

Common Name

English

BENZENEETHANAMINE, N-ETHYL-.ALPHA.-METHYL-3-(TRIFLUOROMETHYL)-, (R)-

Systematic Name

English

J50.055K

Code

English

levofenfluramine [INN]

Common Name

English

(-)-(R)-N-ETHYL-.ALPHA.-METHYL-M-(TRIFLUOROMETHYL)PHENETHYLAMINE

Systematic Name

English

FENFLURAMINE L-FORM

Common Name

English

FENFLURAMINE L-FORM [MI]

Common Name

English

FENFLURAMINE, L-

Common Name

English

Classification Tree Code System Code

DEA NO.

1670