Benperidol

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

MedKoo CAT#: 329305

CAS#: 2062-84-2

Description: Benperidol, also known as Anquil and R-4584, is a butyrophenone antipsychotic, with the highest neuroleptic potency in terms of D2 receptor blockade. Benperidol can be used for positron emission tomography (PET) measurements of D(2)-like dopamine receptor binding in vivo.


Price and Availability

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Benperidol (Anquil, R-4584) 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#: 329305
Name: Benperidol
CAS#: 2062-84-2
Chemical Formula: C22H24FN3O2
Exact Mass: 381.1853
Molecular Weight: 381.4514
Elemental Analysis: C, 69.27; H, 6.34; F, 4.98; N, 11.02; O, 8.39


Related CAS #: 74298-73-0 (HCl)   2062-84-2 (free base)  

Synonym: Benperidol; R-4584; R 4584; R4584; Anquil; McN-JR-4584; McN JR 4584; McNJR4584

IUPAC/Chemical Name: 1-(1-(4-(4-fluorophenyl)-4-oxobutyl)piperidin-4-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one

InChi Key: FEBOTPHFXYHVPL-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H24FN3O2/c23-17-9-7-16(8-10-17)21(27)6-3-13-25-14-11-18(12-15-25)26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-5,7-10,18H,3,6,11-15H2,(H,24,28)

SMILES Code: O=C1NC2=CC=CC=C2N1C3CCN(CCCC(C4=CC=C(F)C=C4)=O)CC3


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: Eisenstein SA, Antenor-Dorsey JA, Gredysa DM, Koller JM, Bihun EC, Ranck SA, Arbeláez AM, Klein S, Perlmutter JS, Moerlein SM, Black KJ, Hershey T. A comparison of D2 receptor specific binding in obese and normal-weight individuals using PET with (N-[(11)C]methyl)benperidol. Synapse. 2013 Nov;67(11):748-56. doi: 10.1002/syn.21680. PubMed PMID: 23650017; PubMed Central PMCID: PMC3778147.

2: Eisenstein SA, Koller JM, Piccirillo M, Kim A, Antenor-Dorsey JA, Videen TO, Snyder AZ, Karimi M, Moerlein SM, Black KJ, Perlmutter JS, Hershey T. Characterization of extrastriatal D2 in vivo specific binding of [¹⁸F](N-methyl)benperidol using PET. Synapse. 2012 Sep;66(9):770-80. doi: 10.1002/syn.21566. PubMed PMID: 22535514; PubMed Central PMCID: PMC3389593.

3: Antenor-Dorsey JA, Markham J, Moerlein SM, Videen TO, Perlmutter JS. Validation of the reference tissue model for estimation of dopaminergic D2-like receptor binding with [18F](N-methyl)benperidol in humans. Nucl Med Biol. 2008 Apr;35(3):335-41. doi: 10.1016/j.nucmedbio.2007.12.004. PubMed PMID: 18355689; PubMed Central PMCID: PMC2390782.

4: Antenor-Dorsey JA, Laforest R, Moerlein SM, Videen TO, Perlmutter JS. Radiation dosimetry of N-([11C]methyl)benperidol as determined by whole-body PET imaging of primates. Eur J Nucl Med Mol Imaging. 2008 Apr;35(4):771-8. Erratum in: Eur J Nucl Med Mol Imaging. 2013 May;40(5):795-6. Dosage error in published abstract; MEDLINE/PubMed abstract corrected. PubMed PMID: 18071701; PubMed Central PMCID: PMC3017464.

5: Leucht S, Hartung B. Benperidol for schizophrenia. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD003083. Review. PubMed PMID: 15846648.

6: Leucht S, Hartung B. Benperidol for schizophrenia. Cochrane Database Syst Rev. 2002;(1):CD003083. Review. Update in: Cochrane Database Syst Rev. 2005;(2):CD003083. PubMed PMID: 11869652.

7: Schönfeldt-Lecuona C, Juengling FD, Connemann BJ, Reske SN, Spitzer M, Kassubek J. Complete dopamine D2 receptor occupancy without extrapyramidal side effects under benperidol. J Clin Psychopharmacol. 2004 Feb;24(1):97-8. PubMed PMID: 14709957.

8: Nikolaus S, Larisch R, Beu M, Hamacher K, Forutan F, Vosberg H, Müller HW. In vivo measurement of D2 receptor density and affinity for 18F-(3-N-methyl)benperidol in the rat striatum with a PET system for small laboratory animals. J Nucl Med. 2003 Apr;44(4):618-24. PubMed PMID: 12679408.

9: Nikolaus S, Larisch R, Beu M, Vosberg H, Müller-Gärtner HW. Imaging of striatal dopamine D(2) receptors with a PET system for small laboratory animals in comparison with storage phosphor autoradiography: a validation study with (18)F-(N-methyl)benperidol. J Nucl Med. 2001 Nov;42(11):1691-6. PubMed PMID: 11696641.

10: Eisenstein SA, Bischoff AN, Gredysa DM, Antenor-Dorsey JA, Koller JM, Al-Lozi A, Pepino MY, Klein S, Perlmutter JS, Moerlein SM, Black KJ, Hershey T. Emotional Eating Phenotype is Associated with Central Dopamine D2 Receptor Binding Independent of Body Mass Index. Sci Rep. 2015 Jun 12;5:11283. doi: 10.1038/srep11283. PubMed PMID: 26066863; PubMed Central PMCID: PMC4464302.

11: Moerlein SM, Perlmutter JS, Markham J, Welch MJ. In vivo kinetics of [18F](N-methyl)benperidol: a novel PET tracer for assessment of dopaminergic D2-like receptor binding. J Cereb Blood Flow Metab. 1997 Aug;17(8):833-45. PubMed PMID: 9290581.

12: Kreuzer P, Landgrebe M, Wittmann M, Schecklmann M, Poeppl TB, Hajak G, Langguth B. Hypothermia associated with antipsychotic drug use: a clinical case series and review of current literature. J Clin Pharmacol. 2012 Jul;52(7):1090-7. doi: 10.1177/0091270011409233. Review. PubMed PMID: 21956608.

13: Moerlein SM, Perlmutter JS, Cutler PD, Welch MJ. Radiation dosimetry of [18F] (N-methyl)benperidol as determined by whole-body PET imaging of primates. Nucl Med Biol. 1997 May;24(4):311-8. PubMed PMID: 9257329.

14: Bender A, Scheiber J, Glick M, Davies JW, Azzaoui K, Hamon J, Urban L, Whitebread S, Jenkins JL. Analysis of pharmacology data and the prediction of adverse drug reactions and off-target effects from chemical structure. ChemMedChem. 2007 Jun;2(6):861-73. PubMed PMID: 17477341.

15: Biryol I, Ozkan SA. Voltammetric determination of droperidol and benperidol. J Pharm Biomed Anal. 1997 Jul;15(11):1695-701. PubMed PMID: 9260665.