GBR-12935 HCl | CAS# 67469-81-2 | DAT and SLC6A2 inhibitor

MedKoo Cat#: 530917 | Name: GBR-12935 HCl

Description:

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

GBR-12935 is a piperazine derivative which is a potent and selective dopamine reuptake inhibitor. It was originally developed in its 3H radiolabelled form for the purpose of mapping the distribution of dopaminergic neurons in the brain by selective labelling of dopamine transporter proteins. This has led to potential clinical uses in the diagnosis of Parkinson's disease, although selective radioligands such as Ioflupane (¹²³I) are now available for this application. GBR-12935 is now widely used in animal research into Parkinson's disease and the dopamine pathways in the brain.

Chemical Structure

GBR-12935 HCl

CAS#67469-81-2 (2HCl)

Theoretical Analysis

MedKoo Cat#: 530917

Name: GBR-12935 HCl

CAS#: 67469-81-2 (2HCl)

Chemical Formula: C28H36Cl2N2O

Exact Mass: 0.0000

Molecular Weight: 487.51

Elemental Analysis: C, 68.98; H, 7.44; Cl, 14.54; N, 5.75; O, 3.28

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 550.00	2 Weeks
100mg	USD 850.00	2 Weeks
250mg	USD 1,450.00	2 Weeks

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Related CAS #

67469-81-2 (2HCl) 76778-22-8 (free base) 1349767-56-1 (maleate)

Synonym

GBR-12935 HCl; GBR-12935 hydrochloride; GBR-12935 dihydrochloride; GBR 12935; GBR12935

IUPAC/Chemical Name

1-(2 (Diphenylmethoxy)ethyl)-4-(3-phenylpropyl)piperazine dihydrochloride

InChi Key

NQWRSILGEXNJIT-UHFFFAOYSA-N

InChi Code

InChI=1S/C28H34N2O.2ClH/c1-4-11-25(12-5-1)13-10-18-29-19-21-30(22-20-29)23-24-31-28(26-14-6-2-7-15-26)27-16-8-3-9-17-27;;/h1-9,11-12,14-17,28H,10,13,18-24H2;2*1H

SMILES Code

[H]Cl.[H]Cl.N1(CCOC(C2=CC=CC=C2)C3=CC=CC=C3)CCN(CCCC4=CC=CC=C4)CC1

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

>2 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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

GBR 12935 dihydrochloride is a potent, and selective dopamine reuptake inhibitor.

In vitro activity:

GBR-12935 at 20 µM significantly inhibited tumoroid growth (Figure 5A,B). In contrast, the NET inhibitor nisoxetine did not alter tumoroid growth as compared to the untreated control. The MAT inhibitor amitriptyline significantly inhibited tumoroid growth, suggesting that DAT inhibition, but not NET inhibition, was required for tumoroid inhibition. GBR-12935 lowered the cancer cell viability of preformed tumoroids in a concentration-dependent manner (Figure 5C). Thus, DAT inhibition is a common mechanism by which Benz and GBR-12935 inhibit tumor growth. Reference: Cancers (Basel). 2020 Feb 24;12(2):523. https://pubmed.ncbi.nlm.nih.gov/32102440/

In vivo activity:

As illustrated in Figure 7b, 20nM GBR12935 significantly and reversibly increased the frequency of sEPSCs recorded in VTA DA rat neurons (by 48±11%, n=6, p=0.01). Reference: Neuropsychopharmacology. 2009 Jan;34(2):307-18. https://pubmed.ncbi.nlm.nih.gov/18596684/

	Solvent	mg/mL	mM
Solubility
	DMF	2.0	4.10
	DMSO	13.5	27.69
	Water	7.1	14.65

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 487.51 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.

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

Formulation protocol:

1. Sogawa C, Eguchi T, Tran MT, Ishige M, Trin K, Okusha Y, Taha EA, Lu Y, Kawai H, Sogawa N, Takigawa M, Calderwood SK, Okamoto K, Kozaki KI. Antiparkinson Drug Benztropine Suppresses Tumor Growth, Circulating Tumor Cells, and Metastasis by Acting on SLC6A3/DAT and Reducing STAT3. Cancers (Basel). 2020 Feb 24;12(2):523. doi: 10.3390/cancers12020523. PMID: 32102440; PMCID: PMC7072357. 2. Shirasaka Y, Lee N, Duan H, Ho H, Pak J, Wang J. Interspecies comparison of the functional characteristics of plasma membrane monoamine transporter (PMAT) between human, rat and mouse. J Chem Neuroanat. 2017 Oct;83-84:99-106. doi: 10.1016/j.jchemneu.2016.09.006. Epub 2016 Sep 15. PMID: 27641077; PMCID: PMC5352556. 3. Xiao C, Shao XM, Olive MF, Griffin WC 3rd, Li KY, Krnjević K, Zhou C, Ye JH. Ethanol facilitates glutamatergic transmission to dopamine neurons in the ventral tegmental area. Neuropsychopharmacology. 2009 Jan;34(2):307-18. doi: 10.1038/npp.2008.99. Epub 2008 Jul 2. PMID: 18596684; PMCID: PMC2676579.

In vitro protocol:

In vivo protocol:

1. Xiao C, Shao XM, Olive MF, Griffin WC 3rd, Li KY, Krnjević K, Zhou C, Ye JH. Ethanol facilitates glutamatergic transmission to dopamine neurons in the ventral tegmental area. Neuropsychopharmacology. 2009 Jan;34(2):307-18. doi: 10.1038/npp.2008.99. Epub 2008 Jul 2. PMID: 18596684; PMCID: PMC2676579.

1: Sato T, Kitayama S, Morita K, Ikeda T, Dohi T. Changes in seizure susceptibility to local anesthetics by repeated administration of cocaine and nomifensine but not GBR12935: possible involvement of noradrenergic system. Jpn J Pharmacol. 2000 Jul;83(3):265-8. PubMed PMID: 10952077. 2: Bowden C, Cheetham SC, Lowther S, Katona CL, Crompton MR, Horton RW. Dopamine uptake sites, labelled with [3H]GBR12935, in brain samples from depressed suicides and controls. Eur Neuropsychopharmacol. 1997 Nov;7(4):247-52. PubMed PMID: 9443655. 3: Akunne HC, Dersch CM, Cadet JL, Baumann MH, Char GU, Partilla JS, de Costa BR, Rice KC, Carroll FI, Rothman RB. Studies of the biogenic amine transporters. III. Demonstration of two binding sites for [3H]GBR12935 and [3H]BTCP in rat caudate membranes. J Pharmacol Exp Ther. 1994 Mar;268(3):1462-75. PubMed PMID: 7908058. 4: Rothman RB, Lewis B, Dersch C, Xu H, Radesca L, de Costa BR, Rice KC, Kilburn RB, Akunne HC, Pert A. Identification of a GBR12935 homolog, LR1111, which is over 4,000-fold selective for the dopamine transporter, relative to serotonin and norepinephrine transporters. Synapse. 1993 May;14(1):34-9. PubMed PMID: 8511716. 5: Sharif NA, Nunes JL, Kalfayan V, McClelland DL, Rosenkranz RP, Eglen RM, Whiting RL. A pharmacological comparison of [3H]GBR12935 binding to rodent striatal and kidney homogenates: binding to dopamine transporters? Neurochem Int. 1992 Jul;21(1):69-73. PubMed PMID: 1303143. 6: Le WD, Bostwick JR, Appel SH. Use of [3H]-GBR12935 to measure dopaminergic nerve terminal growth into the developing rat striatum. Brain Res Dev Brain Res. 1992 Jun 19;67(2):375-7. PubMed PMID: 1511527. 7: Sharif NA, Nunes JL, Michel AD, Whiting RL. Comparative properties of the dopamine transport complex in dog and rodent brain: striatal [(3)H]GBR12935 binding and [(3)H]dopamine uptake. Neurochem Int. 1989;15(3):325-32. PubMed PMID: 20504502.

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