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Sigma-Aldrich

Mazindol

≥98% (TLC), powder

Synonym(s):

5-(4-Chlorophenyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol

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About This Item

Empirical Formula (Hill Notation):
C16H13ClN2O
CAS Number:
22232-71-9
Molecular Weight:
284.74
EC Number:
244-857-0
MDL number:
MFCD00864480
UNSPSC Code:
12352200
PubChem Substance ID:
24896596
NACRES:
NA.77

Assay

≥98% (TLC)

form

powder

drug control

USDEA Schedule IV; Home Office Schedule 3; psychotrope (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IV (Portugal)

color

white

solubility

DMSO: 10 mg/mL

originator

Wyeth

SMILES string

OC1(C2=CC=C(Cl)C=C2)C3=CC=CC=C3C4=NCCN14

InChI

1S/C16H13ClN2O/c17-12-7-5-11(6-8-12)16(20)14-4-2-1-3-13(14)15-18-9-10-19(15)16/h1-8,20H,9-10H2

InChI key

ZPXSCAKFGYXMGA-UHFFFAOYSA-N

Gene Information

human ... SLC6A2(6530) , SLC6A3(6531) , SLC6A4(6532)
rat ... Htr1a(24473) , Htr2a(29595) , Slc6a3(24898) , Slc6a4(25553)

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Biochem/physiol Actions

Anorectic agent; inhibits the dopamine, norepinephrine and serotonin transporters with Kis of 27.6 nM, 3.2 nM, and 153 nM, respectively.

Features and Benefits

This compound is featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Wyeth. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300,H311 + H331

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

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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Johannes Backs et al.
Cardiovascular research, 67(2), 283-290 (2005-07-12)
Endothelin-1 (ET-1) potentiates norepinephrine (NE)-induced contractile responses. An impairment of cardiac NE re-uptake by the neuronal NE transporter (NET) contributes to an increased NE net release in failing hearts. We hypothesized that both phenomena are caused by ET-1-mediated inhibition of
W Michael Caudle et al.
Neurotoxicology, 26(4), 721-728 (2005-08-23)
Although banned in the 1970s, significant levels of the organochlorine pesticide heptachlor are still present in the environment raising concern over potential human exposure. In particular, organochlorine pesticides have been linked to an increased risk of Parkinson's disease. Studies from
Mari Gabrielsen et al.
European journal of medicinal chemistry, 47(1), 24-37 (2011-11-11)
The two main groups of antidepressant drugs, the tricyclic antidepressants (TCAs) and the selective serotonin reuptake inhibitors (SSRIs), as well as several other compounds, act by inhibiting the serotonin transporter (SERT). However, the binding mode and molecular mechanism of inhibition
Abid Oueslati et al.
The European journal of neuroscience, 22(11), 2765-2774 (2005-12-06)
This study examined the cellular correlates of the akinetic deficits produced in Wistar rats by discrete bilateral 6-hydroxydopamine (6-OHDA) striatal infusions in the dorsolateral striatum, mimicking the preferential denervation of the motor striatal territory in early symptomatic stage of Parkinson's
Kasper Severinsen et al.
Molecular pharmacology, 85(2), 208-217 (2013-11-12)
Mazindol has been explored as a possible agent in cocaine addiction pharmacotherapy. The tetracyclic compound inhibits both the dopamine transporter and the serotonin transporter, and simple chemical modifications considerably alter target selectivity. Mazindol, therefore, is an attractive scaffold for both
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