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MedKoo Cat#: 574169 | Name: Reduced haloperidol
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Description:

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

Reduced haloperidol is an active metabolite of haloperidol formed via reduction of haloperidol by ketone reductase.

Chemical Structure

Reduced haloperidol
Reduced haloperidol
CAS#34104-67-1

Theoretical Analysis

MedKoo Cat#: 574169

Name: Reduced haloperidol

CAS#: 34104-67-1

Chemical Formula: C21H25ClFNO2

Exact Mass: 377.1558

Molecular Weight: 377.88

Elemental Analysis: C, 66.75; H, 6.67; Cl, 9.38; F, 5.03; N, 3.71; O, 8.47

Price and Availability

Size Price Availability Quantity
10mg USD 450.00 2 Weeks
25mg USD 850.00 2 Weeks
50mg USD 1,300.00 4 Weeks
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Synonym
Haloperidol Metabolite II; Reduced haloperidol
IUPAC/Chemical Name
4-(4-chlorophenyl)-1-(4-(4-fluorophenyl)-4-hydroxybutyl)piperidin-4-ol
InChi Key
WNZBBTJFOIOEMP-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H25ClFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,20,25-26H,1-2,11-15H2
SMILES Code
OC1(CCN(CCCC(C2=CC=C(F)C=C2)O)CC1)C3=CC=C(Cl)C=C3
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
>3 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Reduced haloperidol inhibits radioligand binding to sigma-1 and dopamine D2 receptors (Kis = 1.4 and 31 nM, respectively) and stimulates brain-derived neurotrophic factor secretion from CCF-SSTG1 and U87MG astrocytic glial cells. It also inhibits norepinephrine, dopamine, and serotonin (5-HT) reuptake (Kis = 21, 25, and 33 μM, respectively, in COS-7 cells expressing the human transporters).
In vitro activity:
The results from this study demonstrate that reduced haloperidol facilitates the secretion of brain-derived neurotrophic factor from astrocytes by acting as a functionally selective S1R agonist. Reference: Neurochem Int. 2017 May;105:21-31. https://pubmed.ncbi.nlm.nih.gov/28188803/
In vivo activity:
In mice, haloperidol was associated with increased endometrial cancer-specific mortality. These findings indicate that clinical use of haloperidol could potentially be harmful to female patients with endometrial cancer Reference: Cancers (Basel). 2022 Jun 23;14(13):3089. https://pubmed.ncbi.nlm.nih.gov/35804859/
Solvent mg/mL mM
Solubility
DMSO 10.0 26.46
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 377.88 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:
1. Dalwadi DA, Kim S, Schetz JA. Activation of the sigma-1 receptor by haloperidol metabolites facilitates brain-derived neurotrophic factor secretion from human astroglia. Neurochem Int. 2017 May;105:21-31. doi: 10.1016/j.neuint.2017.02.003. Epub 2017 Feb 8. PMID: 28188803; PMCID: PMC5375023. 2. Shin JG, Kane K, Flockhart DA. Potent inhibition of CYP2D6 by haloperidol metabolites: stereoselective inhibition by reduced haloperidol. Br J Clin Pharmacol. 2001 Jan;51(1):45-52. doi: 10.1046/j.1365-2125.2001.01313.x. PMID: 11167668; PMCID: PMC2014431. 3. de Bem Alves AC, Aguiar AS Jr. Caffeine plus haloperidol reduces fatigue in an experimental model of Parkinson's disease - a prospective to A2AR-D2R heterodimer antagonism. Purinergic Signal. 2023 Mar 15. doi: 10.1007/s11302-023-09933-2. Epub ahead of print. PMID: 36918462. 4. Chiang JY, Lei FJ, Chang HJ, Wei ST, Wang CC, Huang YC, Wang HL, Chuang CF, Hu SY, Hsieh CH. Haloperidol Instigates Endometrial Carcinogenesis and Cancer Progression by the NF-κB/CSF-1 Signaling Cascade. Cancers (Basel). 2022 Jun 23;14(13):3089. doi: 10.3390/cancers14133089. PMID: 35804859; PMCID: PMC9265032.
In vitro protocol:
1. Dalwadi DA, Kim S, Schetz JA. Activation of the sigma-1 receptor by haloperidol metabolites facilitates brain-derived neurotrophic factor secretion from human astroglia. Neurochem Int. 2017 May;105:21-31. doi: 10.1016/j.neuint.2017.02.003. Epub 2017 Feb 8. PMID: 28188803; PMCID: PMC5375023. 2. Shin JG, Kane K, Flockhart DA. Potent inhibition of CYP2D6 by haloperidol metabolites: stereoselective inhibition by reduced haloperidol. Br J Clin Pharmacol. 2001 Jan;51(1):45-52. doi: 10.1046/j.1365-2125.2001.01313.x. PMID: 11167668; PMCID: PMC2014431.
In vivo protocol:
1. de Bem Alves AC, Aguiar AS Jr. Caffeine plus haloperidol reduces fatigue in an experimental model of Parkinson's disease - a prospective to A2AR-D2R heterodimer antagonism. Purinergic Signal. 2023 Mar 15. doi: 10.1007/s11302-023-09933-2. Epub ahead of print. PMID: 36918462. 2. Chiang JY, Lei FJ, Chang HJ, Wei ST, Wang CC, Huang YC, Wang HL, Chuang CF, Hu SY, Hsieh CH. Haloperidol Instigates Endometrial Carcinogenesis and Cancer Progression by the NF-κB/CSF-1 Signaling Cascade. Cancers (Basel). 2022 Jun 23;14(13):3089. doi: 10.3390/cancers14133089. PMID: 35804859; PMCID: PMC9265032.
1: Epping-Jordan MP, Girard F, Bessis AS, Mutel V, Boléa C, Derouet F, Bessif A, Mingard B, Barbier S, Paradis JS, Rocher JP, Lütjens R, Kalinichev M, Poli S. Effect of the Metabotropic Glutamate Receptor Type 5 Negative Allosteric Modulator Dipraglurant on Motor and Non-Motor Symptoms of Parkinson's Disease. Cells. 2023 Mar 24;12(7):1004. doi: 10.3390/cells12071004. PMID: 37048075; PMCID: PMC10093229. 2: Gao RD, Taylor M, McInnis T, Chen Z, Gori SS, LaPorte HM, Siegler MA, Neisewander JL, Mach RH, Singh M, Slusher BS, Rais R, Luedtke RR, Tsukamoto T. Synthesis and Pharmacological Characterization of a Difluorinated Analogue of Reduced Haloperidol as a Sigma-1 Receptor Ligand. ACS Chem Neurosci. 2023 Mar 1;14(5):947-957. doi: 10.1021/acschemneuro.2c00791. Epub 2023 Feb 13. PMID: 36780706. 3: Natori Y, Yoshimoto T, Yamamoto T, Ishii A. Identification and quantification of diphenhydramine, haloperidol, and its metabolite, reduced haloperidol in a saponified brain specimen that was immersed in the sea water for more than 10 years. Leg Med (Tokyo). 2023 Mar;61:102188. doi: 10.1016/j.legalmed.2022.102188. Epub 2022 Dec 28. PMID: 36603491. 4: Kabra A, Baghel US, Hano C, Martins N, Khalid M, Sharma R. Neuroprotective potential of Myrica esulenta in Haloperidol induced Parkinson's disease. J Ayurveda Integr Med. 2020 Oct-Dec;11(4):448-454. doi: 10.1016/j.jaim.2020.06.007. Epub 2020 Sep 8. PMID: 32912644; PMCID: PMC7772500. 5: Hsu SS, Liang WZ. Ca2+ signaling as a mechanism of haloperidol- induced cytotoxicity in human astrocytes and assessing the protective role of a Ca2+ chelator. Naunyn Schmiedebergs Arch Pharmacol. 2020 Nov;393(11):2117-2127. doi: 10.1007/s00210-020-01929-8. Epub 2020 Jun 27. PMID: 32594194. 6: Dalwadi DA, Kim S, Schetz JA. Activation of the sigma-1 receptor by haloperidol metabolites facilitates brain-derived neurotrophic factor secretion from human astroglia. Neurochem Int. 2017 May;105:21-31. doi: 10.1016/j.neuint.2017.02.003. Epub 2017 Feb 8. PMID: 28188803; PMCID: PMC5375023. 7: Zastrozhin MS, Smirnov VV, Sychev DA, Savchenko LM, Bryun EA, Matis OA. CYP3A4 activity and haloperidol effects in alcohol addicts. Int J Risk Saf Med. 2015;27 Suppl 1:S23-4. doi: 10.3233/JRS-150676. PMID: 26639694. 8: Patteet L, Maudens KE, Sabbe B, Morrens M, De Doncker M, Neels H. High throughput identification and quantification of 16 antipsychotics and 8 major metabolites in serum using ultra-high performance liquid chromatography-tandem mass spectrometry. Clin Chim Acta. 2014 Feb 15;429:51-8. doi: 10.1016/j.cca.2013.11.024. Epub 2013 Nov 28. PMID: 24291056. 9: Fang J, Song J. In vitro characterization of the oxidation of a pyridinium metabolite of haloperidol by human placenta: the effect of smoking. J Pharm Pharm Sci. 2012;15(4):538-47. doi: 10.18433/j31w20. PMID: 23106957. 10: Revel FG, Moreau JL, Pouzet B, Mory R, Bradaia A, Buchy D, Metzler V, Chaboz S, Groebke Zbinden K, Galley G, Norcross RD, Tuerck D, Bruns A, Morairty SR, Kilduff TS, Wallace TL, Risterucci C, Wettstein JG, Hoener MC. A new perspective for schizophrenia: TAAR1 agonists reveal antipsychotic- and antidepressant-like activity, improve cognition and control body weight. Mol Psychiatry. 2013 May;18(5):543-56. doi: 10.1038/mp.2012.57. Epub 2012 May 29. PMID: 22641180. 11: Bordia T, McIntosh JM, Quik M. Nicotine reduces antipsychotic-induced orofacial dyskinesia in rats. J Pharmacol Exp Ther. 2012 Mar;340(3):612-9. doi: 10.1124/jpet.111.189100. Epub 2011 Dec 5. PMID: 22144565; PMCID: PMC3286320. 12: Olczak M, Duszczyk M, Mierzejewski P, Meyza K, Majewska MD. Persistent behavioral impairments and alterations of brain dopamine system after early postnatal administration of thimerosal in rats. Behav Brain Res. 2011 Sep 30;223(1):107-18. doi: 10.1016/j.bbr.2011.04.026. Epub 2011 Apr 28. PMID: 21549155. 13: Ohno Y, Shimizu S, Imaki J. Effects of tandospirone, a 5-HT1A agonistic anxiolytic agent, on haloperidol-induced catalepsy and forebrain Fos expression in mice. J Pharmacol Sci. 2009 Apr;109(4):593-9. doi: 10.1254/jphs.08313fp. Epub 2009 Apr 7. PMID: 19352073. 14: Entrena JM, Cobos EJ, Nieto FR, Cendán CM, Baeyens JM, Del Pozo E. Antagonism by haloperidol and its metabolites of mechanical hypersensitivity induced by intraplantar capsaicin in mice: role of sigma-1 receptors. Psychopharmacology (Berl). 2009 Jul;205(1):21-33. doi: 10.1007/s00213-009-1513-8. Epub 2009 Mar 27. PMID: 19326101; PMCID: PMC2695546. 15: Abbas A, Roth BL. Pimavanserin tartrate: a 5-HT2A inverse agonist with potential for treating various neuropsychiatric disorders. Expert Opin Pharmacother. 2008 Dec;9(18):3251-9. doi: 10.1517/14656560802532707. PMID: 19040345. 16: Varty GB, Hodgson RA, Pond AJ, Grzelak ME, Parker EM, Hunter JC. The effects of adenosine A2A receptor antagonists on haloperidol-induced movement disorders in primates. Psychopharmacology (Berl). 2008 Oct;200(3):393-401. doi: 10.1007/s00213-008-1214-8. Epub 2008 Jul 3. PMID: 18594798. 17: Cheng LF, Yan D, Turdi S, Kerram P. Biphasic effects of haloperidol on sodium currents in guinea pig ventricular myocytes. Acta Pharmacol Sin. 2007 Jun;28(6):783-8. doi: 10.1111/j.1745-7254.2007.00575.x. PMID: 17506936. 18: Kishikawa N, Hamachi C, Imamura Y, Ohba Y, Nakashima K, Tagawa Y, Kuroda N. Determination of haloperidol and reduced haloperidol in human serum by liquid chromatography after fluorescence labeling based on the Suzuki coupling reaction. Anal Bioanal Chem. 2006 Oct;386(3):719-24. doi: 10.1007/s00216-006-0755-0. Epub 2006 Sep 7. PMID: 16957915. 19: Avent KM, DeVoss JJ, Gillam EM. Cytochrome P450-mediated metabolism of haloperidol and reduced haloperidol to pyridinium metabolites. Chem Res Toxicol. 2006 Jul;19(7):914-20. doi: 10.1021/tx0600090. PMID: 16841959. 20: Higashi Y, Nakamura S, Fujii Y. Sensitive determination of 4-(4-chlorophenyl)-4-hydroxypiperidine, a metabolite of haloperidol, in a rat biological sample by HPLC with fluorescence detection after pre-column derivatization using 4-fluoro-7-nitro-2,1,3-benzoxadiazole. Biomed Chromatogr. 2006 Sep;20(9):964-70. doi: 10.1002/bmc.630. PMID: 16506267.