GBR-12935 maleate
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MedKoo CAT#: 510302

CAS#: 1349767-56-1 (maleate)

Description: GBR-12935 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. (Source: http://en.wikipedia.org/wiki/GBR-12935).

Chemical Structure

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GBR-12935 maleate
CAS# 1349767-56-1 (maleate)
Instruction

Theoretical Analysis

MedKoo Cat#: 510302
Name: GBR-12935 maleate
CAS#: 1349767-56-1 (maleate)
Chemical Formula: C32H38N2O5
Exact Mass: 0.00
Molecular Weight: 530.665
Elemental Analysis: C, 72.43; H, 7.22; N, 5.28; O, 15.07

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

Synonym: GBR12935; GBR 12935; GBR-12935; GBR-12935 maleate

IUPAC/Chemical Name: 1-(2-(benzhydryloxy)ethyl)-4-(3-phenylpropyl)piperazine maleate

InChi Key: QCSMGOCTDJAWRQ-BTJKTKAUSA-N

InChi Code: InChI=1S/C28H34N2O.C4H4O4/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;5-3(6)1-2-4(7)8/h1-9,11-12,14-17,28H,10,13,18-24H2;1-2H,(H,5,6)(H,7,8)/b;2-1-

SMILES Code: O=C(O)/C=C\C(O)=O.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, not in water

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:          

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 530.67 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Zhu J, Green T, Bardo MT, Dwoskin LP. Environmental enrichment enhances sensitization to GBR 12935-induced activity and decreases dopamine transporter function in the medial prefrontal cortex. Behav Brain Res. 2004 Jan 5;148(1-2):107-17. PubMed PMID: 14684252.

2: Govitrapong P, Vilaipun P, Ebadi M. Identification of dopamine transporter in bovine pineal gland using [3H]GBR 12935. J Pineal Res. 2003 Aug;35(1):16-23. PubMed PMID: 12823609.

3: Dutta AK, Davis MC, Fei XS, Beardsley PM, Cook CD, Reith ME. Expansion of structure-activity studies of piperidine analogues of 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine (GBR 12935) compounds by altering substitutions in the N-benzyl moiety and behavioral pharmacology of selected molecules. J Med Chem. 2002 Jan 31;45(3):654-62. PubMed PMID: 11806716.

4: Rahman S, Engleman E, Simon J, McBride WJ. Negative interaction of dopamine D2 receptor antagonists and GBR 12909 and GBR 12935 dopamine uptake inhibitors in the nucleus accumbens. Eur J Pharmacol. 2001 Feb 23;414(1):37-44. PubMed PMID: 11230993.

5: Lewis DB, Matecka D, Zhang Y, Hsin LW, Dersch CM, Stafford D, Glowa JR, Rothman RB, Rice KC. Oxygenated analogues of 1-[2-(Diphenylmethoxy)ethyl]- and 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909) as potential extended-action cocaine-abuse therapeutic agents. J Med Chem. 1999 Dec 2;42(24):5029-42. PubMed PMID: 10585212.

6: Norlén M, Norström A, Spigset O, Allard P. [3H]GBR 12935 binding in platelets from poor and extensive cytochrome P-4502D6 metabolizers. Eur J Pharmacol. 1999 Feb 5;366(2-3):329-32. PubMed PMID: 10082215.

7: Darmani NA. Cocaine and selective monoamine uptake blockers (sertraline, nisoxetine, and GBR 12935) prevent the d-fenfluramine-induced head-twitch response in mice. Pharmacol Biochem Behav. 1998 May;60(1):83-90. PubMed PMID: 9610928.

8: Norlén M, Allard P. [3H]GBR 12935 binding in platelets: a possible association with cytochrome P-450IID6? Eur J Pharmacol. 1997 Aug 6;332(2):227-30. PubMed PMID: 9286626.

9: Hiroi T, Imaoka S, Chow T, Yabusaki Y, Funae Y. Specific binding of 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenyl propyl) piperazine (GBR-12935), an inhibitor of the dopamine transporter, to human CYP2D6. Biochem Pharmacol. 1997 Jun 15;53(12):1937-9. PubMed PMID: 9256169.

10: Matecka D, Lewis D, Rothman RB, Dersch CM, Wojnicki FH, Glowa JR, DeVries AC, Pert A, Rice KC. Heteroaromatic analogs of 1-[2-(diphenylmethoxy)ethyl]- and 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909) as high-affinity dopamine reuptake inhibitors. J Med Chem. 1997 Feb 28;40(5):705-16. PubMed PMID: 9057857.