MedKoo Cat#: 584275 | Name: Bromerguride

Description:

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

Bromerguride is an antipsychotic, dopamine antagonist that has an intermediate to high affinity for 5-HT1A receptors.

Chemical Structure

Bromerguride
Bromerguride
CAS#83455-48-5 (free base)

Theoretical Analysis

MedKoo Cat#: 584275

Name: Bromerguride

CAS#: 83455-48-5 (free base)

Chemical Formula: C20H25BrN4O

Exact Mass: 416.1212

Molecular Weight: 417.35

Elemental Analysis: C, 57.56; H, 6.04; Br, 19.15; N, 13.42; O, 3.83

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 #
83455-49-6 (HBr) 83455-48-5 (free base)
Synonym
2-Bromolisuride; Bromerguride; Bromlisuride;
IUPAC/Chemical Name
3-(2-Bromo-9,10-didehydro-6-methylergolin-8alpha-yl)-1,1-diethylurea
InChi Key
SBHNNNRQZGYOAU-YVEFUNNKSA-N
InChi Code
InChI=1S/C20H25BrN4O/c1-4-25(5-2)20(26)22-12-9-14-13-7-6-8-16-18(13)15(19(21)23-16)10-17(14)24(3)11-12/h6-9,12,17,23H,4-5,10-11H2,1-3H3,(H,22,26)/t12-,17+/m0/s1
SMILES Code
O=C(N[C@@H](C=C12)CN(C)[C@]1([H])CC3=C(Br)NC4=C3C2=CC=C4)N(CC)CC
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

Preparing Stock Solutions

The following data is based on the product molecular weight 417.35 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: Hilderbrand M, Hümpel M, Krause W, Täuber U. Pharmacokinetics of bromerguride, a new dopamine-antagonistic ergot derivative in rat and dog. Eur J Drug Metab Pharmacokinet. 1987 Jan-Mar;12(1):31-40. PubMed PMID: 3609071. 2: Krause W, Sauerbrey N, Gräf KJ. Pharmacokinetics and pharmacodynamics in man of the dopamine antagonist ergot derivative, bromerguride. Eur J Clin Pharmacol. 1986;31(2):165-8. PubMed PMID: 3803415. 3: Martinot JL, Paillère-Martinot ML, Loc'h C, Hardy P, Poirier MF, Mazoyer B, Beaufils B, Mazière B, Allilaire JF, Syrota A. The estimated density of D2 striatal receptors in schizophrenia. A study with positron emission tomography and 76Br-bromolisuride. Br J Psychiatry. 1991 Mar;158:346-50. PubMed PMID: 1827999. 4: Assié MB, Cosi C, Koek W. 5-HT1A receptor agonist properties of the antipsychotic, nemonapride: comparison with bromerguride and clozapine. Eur J Pharmacol. 1997 Sep 10;334(2-3):141-7. PubMed PMID: 9369342. 5: Martinot JL, Paillère-Martinot ML, Loc'h C, Lecrubier Y, Dao-Castellana MH, Aubin F, Allilaire JF, Mazoyer B, Mazière B, Syrota A. Central D2 receptors and negative symptoms of schizophrenia. Br J Psychiatry. 1994 Jan;164(1):27-34. PubMed PMID: 8137107. 6: Pauwels PJ, Tardif S, Wurch T, Colpaert FC. Real-time analysis of dopamine: antagonist interactions at recombinant human D2long receptor upon modulation of its activation state. Br J Pharmacol. 2001 Sep;134(1):88-97. PubMed PMID: 11522600; PubMed Central PMCID: PMC1572932. 7: Delforge J, Loc'h C, Hantraye P, Stulzaft O, Khalili-Varasteh M, Mazière M, Syrota A, Mazière B. Kinetic analysis of central [76Br]bromolisuride binding to dopamine D2 receptors studied by PET. J Cereb Blood Flow Metab. 1991 Nov;11(6):914-25. PubMed PMID: 1834685. 8: Pauwels PJ, Finana F, Tardif S, Wurch T, Colpaert FC. Dynamic dopamine-antagonist interactions at recombinant human dopamine D(2short) receptor: dopamine-bound versus antagonist-bound receptor states. J Pharmacol Exp Ther. 2001 Apr;297(1):133-40. PubMed PMID: 11259537. 9: Löschmann PA, Horowski R, Wachtel H. Bromerguride--an ergoline derivative with atypical neuroleptic properties. Clin Neuropharmacol. 1992;15 Suppl 1 Pt A:263A-264A. PubMed PMID: 1354031. 10: Maziere B, Loc'h C, Stulzaft O, Hantraye P, Ottaviani M, Comar D, Maziere M. [76Br]bromolisuride: a new tool for quantitative in vivo imaging of D-2 dopamine receptors. Eur J Pharmacol. 1986 Aug 15;127(3):239-47. PubMed PMID: 2944753. 11: Fink H, Morgenstern R, Ott T. 2-Bromolisuride, an ergot derivative, with dopamine antagonistic and serotonin agonistic properties. Pharmacol Biochem Behav. 1991 Feb;38(2):321-5. PubMed PMID: 1905409. 12: Wachtel H, Kehr W, Sauer G. Central antidopaminergic properties of 2-bromolisuride, an analogue of the ergot dopamine agonist lisuride. Life Sci. 1983 Dec 26;33(26):2583-97. PubMed PMID: 6607392. 13: Cunningham KA, Callahan PM, Appel JB. Discriminative stimulus properties of lisuride revisited: involvement of dopamine D2 receptors. J Pharmacol Exp Ther. 1987 Apr;241(1):147-51. PubMed PMID: 3553537. 14: Wurch T, Boutet-Robinet EA, Palmier C, Colpaert FC, Pauwels PJ. Constitutive coupling of a chimeric dopamine D2/alpha 1B receptor to the phospholipase C pathway: inverse agonism to silent antagonism by neuroleptic drugs. J Pharmacol Exp Ther. 2003 Jan;304(1):380-90. PubMed PMID: 12490615. 15: Hantraye P, Loc'H C, Maziere B, Khalili-Varasteh M, Crouzel C, Fournier D, Yorke JC, Stulzaft O, Riche D, Isacson O, et al. 6-[18F]fluoro-L-dopa uptake and [76Br]bromolisuride binding in the excitotoxically lesioned caudate-putamen of nonhuman primates studied using positron emission tomography. Exp Neurol. 1992 Feb;115(2):218-27. PubMed PMID: 1531196. 16: Pauwels PJ, Tardif S, Colpaert FC. Differential signalling of both wild-type and Thr(343)Arg dopamine D(2short) receptor by partial agonists in a G-protein-dependent manner. Biochem Pharmacol. 2001 Sep 15;62(6):723-32. PubMed PMID: 11551517. 17: Hümpel M, Sostarek D, Gieschen H, Labitzky C. Studies on the biotransformation of lonazolac, bromerguride, lisuride and terguride in laboratory animals and their hepatocytes. Xenobiotica. 1989 Apr;19(4):361-77. PubMed PMID: 2750201.