Synonym
GBR12935; GBR 12935; GBR-12935; GBR-12935 maleate; GBR 12935 Dimaleate Salt
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
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
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.
| 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: 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.
