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F112

Sigma-Aldrich

(+)-Fenfluramine hydrochloride

Synonym(s):

(+)-N-Ethyl-α-methyl-m-[trifluoromethyl]phenethylamine hydrochloride, Dexfenfluramine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C12H16F3N · HCl
CAS Number:
3239-45-0
Molecular Weight:
267.72
EC Number:
221-806-0
MDL number:
MFCD00069276
UNSPSC Code:
12352116
PubChem Substance ID:
24894746
NACRES:
NA.77

form

powder

drug control

USDEA Schedule IV

color

white to off-white

solubility

H2O: soluble 10 mg/mL

application(s)

forensics and toxicology

storage temp.

room temp

SMILES string

Cl[H].CCN[C@@H](C)Cc1cccc(c1)C(F)(F)F

InChI

1S/C12H16F3N.ClH/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;1H/t9-;/m0./s1

InChI key

ZXKXJHAOUFHNAS-FVGYRXGTSA-N

Gene Information

human ... HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR1E(3354) , HTR1F(3355) , HTR2A(3356) , HTR2B(3357) , HTR2C(3358) , HTR3A(3359) , HTR3B(9177) , HTR3C(170572) , HTR3D(200909) , HTR3E(285242) , HTR4(3360) , HTR5A(3361) , HTR6(3362) , HTR7(3363)

Biochem/physiol Actions

(+)-Fenfluramine is a serotonin uptake inhibitor; anoxexic. (+)-Fenfluramine is neurotoxic on prolonged administration or at high dosage. (+)-Fenfluramine releases serotonin from axon terminals by a nonexocytotic mechanism.

Other Notes

Active isomer

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Delphine Natali et al.
Chest, 140(4), 1066-1068 (2011-10-06)
We report a case of pulmonary arterial hypertension (PAH) occurring in a patient with Cowden syndrome with a mutation in the phosphatase and tensin (PTEN) tumor suppressor gene, in the context of exposure to the appetite suppressant dexfenfluramine. Anorexigen exposure
Margaret R Maclean et al.
Advances in experimental medicine and biology, 661, 309-322 (2010-03-06)
The serotonin hypothesis of pulmonary arterial hypertension (PAH) arose after an outbreak of PAH in patients taking the anorexigenic drugs aminorex and dexfenfluramine. Both of these drugs are serotonin transporter (SERT) substrates and indirect serotinergic agonists. There is now a
Effects of d- and 1-fenfluramine on striatal homovanillic acid concentrations in rats after pharmacological manipulation of brain serotonin.
V Crunelli et al.
Pharmacological research communications, 12(3), 215-223 (1980-03-01)
Nicolas Desbuards et al.
European journal of pharmacology, 602(2-3), 355-363 (2008-12-04)
The anorectic drug, dexfenfluramine has been associated with an increase in the relative risk of developing pulmonary hypertension. 5-hydroxytryptamine (5-HT) is a mitogen for smooth muscle cell, an effect that relies on 5-HT transporter expression and which has been proposed
Richard W Foltin
Physiology & behavior, 103(5), 493-500 (2011-04-23)
We examined the effects of periodic access to a palatable, high sugar content food (candy) in 8 male baboons on the anorectic response to d-amphetamine, which increases dopamine, and dexfenfluramine, which increases serotonin. During candy access, up to 200 candies
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