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N1530

Sigma-Aldrich

Nomifensine maleate salt

Synonym(s):

1,2,3,4-Tetrahydro-2-methyl-4-phenyl-8-isoquinolinamine maleate salt

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About This Item

Empirical Formula (Hill Notation):
C16H18N2 · C4H4O4
CAS Number:
32795-47-4
Molecular Weight:
354.40
EC Number:
251-223-7
MDL number:
MFCD00069320
UNSPSC Code:
12352200
PubChem Substance ID:
24277920
NACRES:
NA.77

form

powder

Quality Level

200

SMILES string

[H]\C(=C(/[H])C(O)=O)C(O)=O.CN1CC(c2ccccc2)c3cccc(N)c3C1

InChI

1S/C16H18N2.C4H4O4/c1-18-10-14(12-6-3-2-4-7-12)13-8-5-9-16(17)15(13)11-18;5-3(6)1-2-4(7)8/h2-9,14H,10-11,17H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

InChI key

GEOCVSMCLVIOEV-BTJKTKAUSA-N

Gene Information

human ... DBH(1621) , SLC6A2(6530) , SLC6A3(6531) , SLC6A4(6532)

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Application

Nomifensine maleate salt has been used to study the β-CFT (cocaine analogue) binding using human embryonic kidney 293T cells.

Biochem/physiol Actions

Nomifensine maleate is a selective dopamine uptake inhibitor interacting with the dopamine transporter, at a site different from that of cocaine; antidepressant. Nomifensine serves as an antidepressant and is known to cause frequent hemolytic anemia. The aniline group in this compound results in blood and liver toxicities.

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Metabolism of nomifensine to a dihydroisoquinolinium ion metabolite by human myeloperoxidase, hemoglobin, monoamine oxidase-A, and cytochrome P450 enzymes
Obach RS and Dalvie DK
Drug Metabolism and Disposition (2006)
Matthew Dunn et al.
Nature communications, 9(1), 2838-2838 (2018-07-22)
Norepinephrine is a monoamine neurotransmitter with a wide repertoire of physiological roles in the peripheral and central nervous systems. There are, however, no experimental means to study functional properties of individual noradrenergic synapses in the brain. Development of new approaches
Melatonin receptors limit dopamine reuptake by regulating dopamine transporter cell-surface exposure
Benleulmi-Chaachoua A, et al.
Cellular and Molecular Life Sciences, 75(23), 4357-4370 (2018)
Yoonbae Oh et al.
Biosensors & bioelectronics, 121, 174-182 (2018-09-16)
For over two decades, fast-scan cyclic voltammetry (FSCV) has served as a reliable analytical method for monitoring dopamine release in near real-time in vivo. However, contemporary FSCV techniques have been limited to measure only rapid (on the order of seconds
S M Meiergerd et al.
Journal of neurochemistry, 63(5), 1683-1692 (1994-11-01)
The inhibition by cocaine of the apparent initial rate of the transport of striatal dopamine was compared with inhibitions produced by cocaethylene, benztropine, GBR-12909, mazindol, and nomifensine. Rotating disk electrode voltammetry was used to measure the kinetically resolved, inwardly directed
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