LEVOFENFLURAMINE (+)-CAMPHORATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H16F3N.C10H16O4
Molecular Weight	431.489
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of LEVOFENFLURAMINE (+)-CAMPHORATE

Structure Search

SMILES

CC1(C)[C@H](CC[C@@]1(C)C(O)=O)C(O)=O.CCN[C@H](C)CC2=CC(=CC=C2)C(F)(F)F

InChI

InChIKey=GBMYZGXLAHAFPC-HJYVOTIRSA-N

InChI=1S/C12H16F3N.C10H16O4/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15;1-9(2)6(7(11)12)4-5-10(9,3)8(13)14/h4-6,8-9,16H,3,7H2,1-2H3;6H,4-5H2,1-3H3,(H,11,12)(H,13,14)/t9-;6-,10+/m11/s1

HIDE SMILES / InChI

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

Name

Type

Language

LEVOFENFLURAMINE (+)-CAMPHORATE

Common Name

English

1,3-CYCLOPENTANEDICARBOXYLIC ACID, 1,2,2-TRIMETHYL-, (1R-CIS)-, COMPD. WITH (R)-N-ETHYL-.ALPHA.-METHYL-3-(TRIFLUOROMETHYL)BENZENEETHANAMINE (1:1)

Systematic Name

English

CAMPHORIC ACID, COMPOUND WITH (R)-N-ETHYL-ALPHA-METHYL-3-(TRIFLUOROMETHYL)PHENETHYLAMINE (1:1)

Common Name

English

BENZENEETHANAMINE, N-ETHYL-.ALPHA.-METHYL-3-(TRIFLUOROMETHYL)-, (R)-, (1R-CIS)-1,2,2-TRIMETHYL-1,3-CYCLOPENTANEDICARBOXYLATE (1:1)

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID30242739