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MedKoo Cat#: 599293 | Name: Indatraline

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Indatraline is a nonselective monoamine transporter inhibitor.

Chemical Structure

Indatraline
Indatraline
CAS#86939-10-8 (free base)

Theoretical Analysis

MedKoo Cat#: 599293

Name: Indatraline

CAS#: 86939-10-8 (free base)

Chemical Formula: C16H15Cl2N

Exact Mass: 291.0582

Molecular Weight: 292.20

Elemental Analysis: C, 65.77; H, 5.17; Cl, 24.26; N, 4.79

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
86939-40-4 (HCl)
Synonym
Indatraline; Lu 19005; Lu-19005; Lu19005
IUPAC/Chemical Name
(1S,3R)-3-(3,4-dichlorophenyl)-N-methyl-2,3-dihydro-1H-inden-1-amine
InChi Key
SVFXPTLYMIXFRX-CJNGLKHVSA-N
InChi Code
InChI=1S/C16H15Cl2N/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/t13-,16+/m1/s1
SMILES Code
CN[C@H]1C[C@H](C2=CC=C(Cl)C(Cl)=C2)C3=C1C=CC=C3
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 292.20 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Allmendinger L, Wanner KT. Synthesis of [2H7]indatraline. J Labelled Comp Radiopharm. 2014 Nov;57(13):721-4. doi: 10.1002/jlcr.3245. Epub 2014 Nov 9. PubMed PMID: 25382822. 2: Heo JC, Jung TH, Jung DY, Park WK, Cho H. Indatraline inhibits Rho- and calcium-mediated glioblastoma cell motility and angiogenesis. Biochem Biophys Res Commun. 2014 Jan 10;443(2):749-55. doi: 10.1016/j.bbrc.2013.12.046. Epub 2013 Dec 12. PubMed PMID: 24333442. 3: Grimm SH, Höfner G, Wanner KT. MS Binding Assays for the Three Monoamine Transporters Using the Triple Reuptake Inhibitor (1R,3S)-Indatraline as Native Marker. ChemMedChem. 2015 Jun;10(6):1027-39. doi: 10.1002/cmdc.201500084. Epub 2015 Apr 20. PubMed PMID: 25899387. 4: Grimm SH, Höfner G, Wanner KT. Development and validation of an LC-ESI-MS/MS method for the triple reuptake inhibitor indatraline enabling its quantification in MS Binding Assays. Anal Bioanal Chem. 2015 Jan;407(2):471-85. doi: 10.1007/s00216-014-8312-8. Epub 2014 Dec 2. PubMed PMID: 25450050. 5: Cho YS, Yen CN, Shim JS, Kang DH, Kang SW, Liu JO, Kwon HJ. Antidepressant indatraline induces autophagy and inhibits restenosis via suppression of mTOR/S6 kinase signaling pathway. Sci Rep. 2016 Oct 3;6:34655. doi: 10.1038/srep34655. PubMed PMID: 27694974; PubMed Central PMCID: PMC5046148. 6: Grimm SH, Allmendinger L, Höfner G, Wanner KT. Enantiopurity determination of the enantiomers of the triple reuptake inhibitor indatraline. Chirality. 2013 Dec;25(12):923-33. doi: 10.1002/chir.22235. Epub 2013 Oct 7. PubMed PMID: 24123410. 7: Kameyama M, Siqueira FA, Garcia-Mijares M, Silva LF Jr, Silva MT. Indatraline: synthesis and effect on the motor activity of Wistar rats. Molecules. 2011 Nov 10;16(11):9421-38. doi: 10.3390/molecules16119421. PubMed PMID: 22075572. 8: Walton JG, Jones DC, Kiuru P, Durie AJ, Westwood NJ, Fairlamb AH. Synthesis and evaluation of indatraline-based inhibitors for trypanothione reductase. ChemMedChem. 2011 Feb 7;6(2):321-8. doi: 10.1002/cmdc.201000442. Epub 2010 Dec 15. PubMed PMID: 21275055; PubMed Central PMCID: PMC3047706. 9: Roesner S, Casatejada JM, Elford TG, Sonawane RP, Aggarwal VK. Enantioselective syntheses of (+)-sertraline and (+)-indatraline using lithiation/borylation-protodeboronation methodology. Org Lett. 2011 Nov 4;13(21):5740-3. doi: 10.1021/ol202251p. Epub 2011 Oct 13. PubMed PMID: 21995597. 10: Mello NK, Negus SS. Effects of indatraline and buprenorphine on self-administration of speedball combinations of cocaine and heroin by rhesus monkeys. Neuropsychopharmacology. 2001 Jul;25(1):104-17. PubMed PMID: 11377924. 11: Wei WT, Yeh JY, Kuo TS, Wu HL. Highly enantioselective rhodium-catalyzed asymmetric 1,4-addition reactions of arylboronic acids to acyclic α,β-unsaturated compounds: the formal synthesis of (-)-indatraline. Chemistry. 2011 Oct 4;17(41):11405-9. doi: 10.1002/chem.201102073. Epub 2011 Aug 31. PubMed PMID: 21882278. 12: Hache G, Guiard BP, Nguyen TH, Quesseveur G, Gardier AM, Peters D, Munro G, Coudoré F. Antinociceptive activity of the new triple reuptake inhibitor NS18283 in a mouse model of chemotherapy-induced neuropathic pain. Eur J Pain. 2015 Mar;19(3):322-33. doi: 10.1002/ejp.550. PubMed PMID: 25045036. 13: Gu XH, Yu H, Jacobson AE, Rothman RB, Dersch CM, George C, Flippen-Anderson JL, Rice KC. Design, synthesis, and monoamine transporter binding site affinities of methoxy derivatives of indatraline. J Med Chem. 2000 Dec 14;43(25):4868-76. PubMed PMID: 11123996. 14: Partilla JS, Dersch CM, Yu H, Rice KC, Rothman RB. Neurochemical neutralization of amphetamine-type stimulants in rat brain by the indatraline analog (-)-HY038. Brain Res Bull. 2000 Dec;53(6):821-6. PubMed PMID: 11179849. 15: Li Y, McGreal S, Zhao J, Huang R, Zhou Y, Zhong H, Xia M, Ding WX. A cell-based quantitative high-throughput image screening identified novel autophagy modulators. Pharmacol Res. 2016 Aug;110:35-49. doi: 10.1016/j.phrs.2016.05.004. Epub 2016 May 7. PubMed PMID: 27168224; PubMed Central PMCID: PMC4995889. 16: Taylor JG, Correia CR. Stereoselective synthesis of unsymmetrical β,β-diarylacrylates by a Heck-Matsuda reaction: versatile building blocks for asymmetric synthesis of β,β-diphenylpropanoates, 3-aryl-indole, and 4-aryl-3,4-dihydro-quinolin-2-one and formal synthesis of (-)-indatraline. J Org Chem. 2011 Feb 4;76(3):857-69. doi: 10.1021/jo102134v. Epub 2011 Jan 11. Erratum in: J Org Chem. 2012 Jun 1;77(11):5220. PubMed PMID: 21241065. 17: Silva LF Jr, Siqueira FA, Pedrozo EC, Vieira FY, Doriguetto AC. Iodine(III)-promoted ring contraction of 1,2-dihydronaphthalenes: a diastereoselective total synthesis of (+/-)-indatraline. Org Lett. 2007 Apr 12;9(8):1433-6. Epub 2007 Mar 20. PubMed PMID: 17371034. 18: Schenk S. Effects of GBR 12909, WIN 35,428 and indatraline on cocaine self-administration and cocaine seeking in rats. Psychopharmacology (Berl). 2002 Mar;160(3):263-70. Epub 2002 Jan 24. PubMed PMID: 11889495. 19: Negus SS, Brandt MR, Mello NK. Effects of the long-acting monoamine reuptake inhibitor indatraline on cocaine self-administration in rhesus monkeys. J Pharmacol Exp Ther. 1999 Oct;291(1):60-9. PubMed PMID: 10490887. 20: Yen CN, Cho YS, Kwon HJ. The effect of indatraline on angiogenesis suppression through HIF-1α-mediated VEGF inhibition. Biochem Biophys Res Commun. 2017 Apr 1;485(2):349-354. doi: 10.1016/j.bbrc.2017.02.077. Epub 2017 Feb 17. PubMed PMID: 28216154.