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M2017

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
NACRES:
NA.77
PubChem Substance ID:
24896596
UNSPSC Code:
12352200
EC Number:
244-857-0
MDL number:
MFCD00864480
Assay:
≥98% (TLC)
Form:
powder

Key Documents

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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); Pszichotróp anyag / Psychotropic Substance (Hungary), 78/2022. (XII. 28.) BM rendelet, kontrollierte Droge in Deutschland

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)

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.
Anorectic agent; inhibits the dopamine, norepinephrine and serotonin transporters.

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.

Legal Information

German
Dieses Produkt fällt unter das Betäubungsmittelgesetz (BtMG). Für eine Bestellung dieses Produktes ist eine Erlaubnis nach § 3 BtMG zwingend erforderlich, es sei denn, es greift eine Ausnahme von der Erlaubnispflicht nach § 4 oder § 26 BtMG.

English
This product is subject to the German Narcotics Act. A permit under Section 3 of the German Narcotics Act is mandatory for ordering this product unless an exemption from the permit requirement under Section 4 or Section 26 of the German Narcotics Act applies.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
13181151
0000079596
0000088608
028M4167V
019M4004V

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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
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
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
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
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
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