BD-1008 HBr

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

MedKoo CAT#: 530480

CAS#: 138356-09-9 (HBr)

Description: BD1008 is a selective antagonist of the sigma 1 (σ1) receptor (Ki = 2 nM) that displays 4-fold selectivity for σ1 over σ2. BD-1008 attenuate the toxicity and stimulant effects of cocaine through antagonism of sigma receptors


Price and Availability

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BD 1008 (hydrobromide) is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 530480
Name: BD-1008 HBr
CAS#: 138356-09-9 (HBr)
Chemical Formula: C15H24Br2Cl2N2
Exact Mass:
Molecular Weight: 463.079
Elemental Analysis: C, 38.91; H, 5.22; Br, 34.51; Cl, 15.31; N, 6.05


Synonym: BD1008; BD-1008; BD 1008.

IUPAC/Chemical Name: N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-1-pyrrolidineethanamine, dihydrobromide

InChi Key: YTBUMHOSKIAYCZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H22Cl2N2.2BrH/c1-18(10-11-19-7-2-3-8-19)9-6-13-4-5-14(16)15(17)12-13;;/h4-5,12H,2-3,6-11H2,1H3;2*1H

SMILES Code: CN(CCC1=CC=C(Cl)C(Cl)=C1)CCN2CCCC2.[H]Br.[H]Br


Technical Data

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).

Harmonized System Code:
293490


References

1: Matsumoto RR, Gilmore DL, Pouw B, Bowen WD, Williams W, Kausar A, Coop A. Novel analogs of the sigma receptor ligand BD1008 attenuate cocaine-induced toxicity in mice. Eur J Pharmacol. 2004 May 10;492(1):21-6. PubMed PMID: 15145701.

2: Matsumoto RR, McCracken KA, Pouw B, Miller J, Bowen WD, Williams W, De Costa BR. N-alkyl substituted analogs of the sigma receptor ligand BD1008 and traditional sigma receptor ligands affect cocaine-induced convulsions and lethality in mice. Eur J Pharmacol. 2001 Jan 12;411(3):261-73. PubMed PMID: 11164383.

3: Matsumoto RR, McCracken KA, Friedman MJ, Pouw B, De Costa BR, Bowen WD. Conformationally restricted analogs of BD1008 and an antisense oligodeoxynucleotide targeting sigma1 receptors produce anti-cocaine effects in mice. Eur J Pharmacol. 2001 May 11;419(2-3):163-74. PubMed PMID: 11426838.

4: Maeda DY, Williams W, Bowen WD, Coop A. A sigma-1 receptor selective analogue of BD1008. A potential substitute for (+)-opioids in sigma receptor binding assays. Bioorg Med Chem Lett. 2000 Jan 3;10(1):17-8. PubMed PMID: 10636233.

5: Garcés-Ramírez L, Green JL, Hiranita T, Kopajtic TA, Mereu M, Thomas AM, Mesangeau C, Narayanan S, McCurdy CR, Katz JL, Tanda G. Sigma receptor agonists: receptor binding and effects on mesolimbic dopamine neurotransmission assessed by microdialysis. Biol Psychiatry. 2011 Feb 1;69(3):208-17. doi: 10.1016/j.biopsych.2010.07.026. PubMed PMID: 20950794; PubMed Central PMCID: PMC3015019.

6: McCracken KA, Bowen WD, Matsumoto RR. Novel sigma receptor ligands attenuate the locomotor stimulatory effects of cocaine. Eur J Pharmacol. 1999 Jan 15;365(1):35-8. PubMed PMID: 9988120.

7: Brent PJ, Saunders H, Dunkley PR. Intrasynaptosomal free calcium levels in rat forebrain synaptosomes: modulation by sigma (sigma) receptor ligands. Neurosci Lett. 1996 Jun 21;211(2):138-42. PubMed PMID: 8830864.

8: Maurice T, Phan VL, Noda Y, Yamada K, Privat A, Nabeshima T. The attenuation of learning impairments induced after exposure to CO or trimethyltin in mice by sigma (sigma) receptor ligands involves both sigma1 and sigma2 sites. Br J Pharmacol. 1999 May;127(2):335-42. PubMed PMID: 10385231; PubMed Central PMCID: PMC1566026.

9: Monnet FP, de Costa BR, Bowen WD. Differentiation of sigma ligand-activated receptor subtypes that modulate NMDA-evoked [3H]-noradrenaline release in rat hippocampal slices. Br J Pharmacol. 1996 Sep;119(1):65-72. PubMed PMID: 8872358; PubMed Central PMCID: PMC1915737.

10: Ault DT, Werling LL. Differential modulation of NMDA-stimulated [3H]dopamine release from rat striatum by neuropeptide Y and sigma receptor ligands. Brain Res. 1997 Jun 20;760(1-2):210-7. PubMed PMID: 9237537.

11: Desai RI, Grandy DK, Lupica CR, Katz JL. Pharmacological characterization of a dopamine transporter ligand that functions as a cocaine antagonist. J Pharmacol Exp Ther. 2014 Jan;348(1):106-15. doi: 10.1124/jpet.113.208538. PubMed PMID: 24194528; PubMed Central PMCID: PMC3868881.

12: Hiranita T, Soto PL, Tanda G, Kopajtic TA, Katz JL. Stimulants as specific inducers of dopamine-independent σ agonist self-administration in rats. J Pharmacol Exp Ther. 2013 Oct;347(1):20-9. doi: 10.1124/jpet.113.207522. PubMed PMID: 23908387; PubMed Central PMCID: PMC3781409.

13: Couture S, Debonnel G. Modulation of the neuronal response to N-methyl-D-aspartate by selective sigma2 ligands. Synapse. 1998 May;29(1):62-71. PubMed PMID: 9552175.

14: Hiranita T, Soto PL, Kohut SJ, Kopajtic T, Cao J, Newman AH, Tanda G, Katz JL. Decreases in cocaine self-administration with dual inhibition of the dopamine transporter and σ receptors. J Pharmacol Exp Ther. 2011 Nov;339(2):662-77. doi: 10.1124/jpet.111.185025. PubMed PMID: 21859929; PubMed Central PMCID: PMC3199989.

15: Beninger RJ. International Behavioral Neuroscience Society - Ninth meeting. Neurochemistry of feeding. IDrugs. 2000 Jul;3(7):745-6. PubMed PMID: 16080042.

16: Hiranita T, Soto PL, Tanda G, Katz JL. Reinforcing effects of sigma-receptor agonists in rats trained to self-administer cocaine. J Pharmacol Exp Ther. 2010 Feb;332(2):515-24. doi: 10.1124/jpet.109.159236. PubMed PMID: 19892920; PubMed Central PMCID: PMC2812106.

17: Connelly S, Line K, Isupov MN, Littlechild JA. Synthesis and characterisation of a ligand that forms a stable tetrahedral intermediate in the active site of the Aureobacterium species (-) gamma-lactamase. Org Biomol Chem. 2005 Sep 21;3(18):3260-2. PubMed PMID: 16132085.

18: Martin WJ, De Costa BR, Walker JM. Effects of sigma ligands on rat cerebellar Purkinje neuron firing: an iontophoretic study. Brain Res Bull. 1994;35(4):303-9. PubMed PMID: 7850479.

19: Daniels A, Ayala E, Chen W, Coop A, Matsumoto RR. N-[2-(m-methoxyphenyl)ethyl]-N-ethyl-2-(1-pyrrolidinyl)ethylamine (UMB 116) is a novel antagonist for cocaine-induced effects. Eur J Pharmacol. 2006 Aug 7;542(1-3):61-8. PubMed PMID: 16797004.

20: Matsumoto RR, McCracken KA, Pouw B, Zhang Y, Bowen WD. Involvement of sigma receptors in the behavioral effects of cocaine: evidence from novel ligands and antisense oligodeoxynucleotides. Neuropharmacology. 2002 Jun;42(8):1043-55. PubMed PMID: 12128006.