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I119

Sigma-Aldrich

Indatraline hydrochloride

solid

Synonym(s):

(±)-trans-3-(3,4-Dichlorophenyl)-N-methyl-1-indanamine hydrochloride, Lu 19-005

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About This Item

Empirical Formula (Hill Notation):
C16H15Cl2N · HCl
CAS Number:
96850-13-4
Molecular Weight:
328.66
MDL number:
MFCD00083178
UNSPSC Code:
12352200
PubChem Substance ID:
24277939
NACRES:
NA.77

form

solid

color

white

solubility

H2O: 2 mg/mL

storage temp.

2-8°C

SMILES string

Cl.CN[C@@H]1C[C@@H](c2ccc(Cl)c(Cl)c2)c3ccccc13

InChI

1S/C16H15Cl2N.ClH/c1-19-16-9-13(11-4-2-3-5-12(11)16)10-6-7-14(17)15(18)8-10;/h2-8,13,16,19H,9H2,1H3;1H/t13-,16+;/m0./s1

InChI key

QICQDZXGZOVTEF-MELYUZJYSA-N

Gene Information

human ... DRD1(1812) , DRD2(1813) , DRD3(1814) , DRD4(1815) , DRD5(1816) , 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) , HTR5B(645694) , HTR6(3362) , HTR7(3363)

Application

Indatraline hydrochloride has been used:
  • as a competitive inhibitor of 3H-dopamine ([3H]DA) to study its effects on trans-activator of transcription (Tat) protein on cocaine-induced inhibition of uptake of [3H]DA
  • as a dopamine transport blocker to study its effects on trace amine-associated receptor 1 (TAAR1)-transfected mice cells
  • as a nonselective monoamine transport inhibitor to study its anti-angiogenic activities in glioblastoma multiforme (GBM)

Biochem/physiol Actions

Indatraline is a non-selective monoamine transport inhibitor. It inhibits the reuptake of neurotransmitters, such as serotonin, norepinephrine and dopamine. It exhibits anti-depressant and anti-angiogenic effects. Indatraline also plays a role in inducing autophagy.

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.

Legal Information

Sold with the permission of H. Lundbeck A/S.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

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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S Rosenzweig-Lipson et al.
Psychopharmacology, 107(2-3), 186-194 (1992-01-01)
The effects of the monoamine uptake inhibitor Lu 19-005 ((+/-)-trans-3-(3,4-dichlorophenyl)-N-methyl-1-indanamine) and its (+) and (-) enantiomers, Lu 20-042 and Lu 20-043, were compared with those of cocaine and the selective dopamine uptake inhibitor GBR 12909 (1-(2-[bis(4-fluorophenyl)methoxy]ethyl)-4-(3-phenylpropyl)piperazine) in behavioral and radioligand
J Arnt et al.
Naunyn-Schmiedeberg's archives of pharmacology, 329(2), 101-107 (1985-04-01)
Behavioural effects on dopaminergic transmission of a phenylindane derivative, Lu 19-005 [(+/-)-trans-3-(3,4-dichlorophenyl)-N-methyl-l-indanamine, HCI], with potent inhibitory effect on dopamine (DA), noradrenaline (NA) and serotonin (5-HT) uptake in rats and the effect on DA, NA and 5-HT activity in mice have
J Hyttel et al.
Journal of neurochemistry, 44(5), 1615-1622 (1985-05-01)
The neurochemical profile of a new compound, Lu 19-005 [(+/-)trans-3-(3,4-dichlorophenyl)-N-methyl-1-indanamine hydrochloride], has been investigated. Lu 19-005 is a potent inhibitor of the synaptosomal uptake of 3,4-dihydroxyphenylethylamine (dopamine, DA), noradrenaline (NA), and 5-hydroxytryptamine (5-HT, serotonin). In this respect it resembles diclofensine
Recombinant HIV-1TAT1-86 allosterically modulates dopamine transporter activity
Zhu J, et al.
Synapse, 65(11), 1251-1251 (2011)
M Laruelle et al.
Synapse (New York, N.Y.), 13(4), 295-309 (1993-04-01)
Single photon emission computed tomography (SPECT) studies of regional kinetic uptake and pharmacological specificity of [123I]methyl 3 beta-(4-iodophenyl) tropane-2 beta-carboxylate ([123I]beta-CIT) were performed in nonhuman primates (n = 41). In control experiments, activity was concentrated in striatum and in hypothalamic/midbrain
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