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MedKoo Cat#: 527019 | Name: Diphenidol hydrochloride
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Description:

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

Diphenidol hydrochloride is a muscarinic antagonist, exerting an anticholinergic effect due to interactions with mACh receptors, particularly M1, M2, M3 and M4.

Chemical Structure

Diphenidol hydrochloride
Diphenidol hydrochloride
CAS#3254-89-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 527019

Name: Diphenidol hydrochloride

CAS#: 3254-89-5 (HCl)

Chemical Formula: C21H28ClNO

Exact Mass: 0.0000

Molecular Weight: 345.91

Elemental Analysis: C, 72.92; H, 8.16; Cl, 10.25; N, 4.05; O, 4.63

Price and Availability

Size Price Availability Quantity
10g USD 250.00 2 Weeks
25g USD 450.00 2 Weeks
50g USD 750.00 2 Weeks
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Related CAS #
26363-46-2 (pamoate) 3254-89-5 (HCl) 972-02-1 (free base)
Synonym
Diphenidol hydrochloride; difenidol hydrochloride; Diphenidol HCl; SKF 478A; SKF478A; SKF-478A
IUPAC/Chemical Name
1,1-Diphenyl-4-piperidin-1-ylbutan-1-ol hydrochloride
InChi Key
AVZIYZHXZAYGJS-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H27NO.ClH/c23-21(19-11-4-1-5-12-19,20-13-6-2-7-14-20)15-10-18-22-16-8-3-9-17-22;/h1-2,4-7,11-14,23H,3,8-10,15-18H2;1H
SMILES Code
OC(C1=CC=CC=C1)(C2=CC=CC=C2)CCCN3CCCCC3.[H]Cl
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Diphenidol hydrochloride (Difenidol hydrochloride) is a non-selective muscarinic M1-M4 receptor antagonist, has anti-arrhythmic activity. Diphenidol hydrochloride is also a potent non-specific blocker of voltage-gated ion channels (Na+, K+, and Ca2+) in neuronal cells.
In vitro activity:
Electrophysiological experiments were performed to study ion channel activities in two neuronal cell lines, namely, neuroblastoma N2A cells and differentiated NG108-15 cells. Diphenidol inhibited voltage-gated K(+) channels and Ca(2+) channels, but did not affect store-operated Ca(2+) channels. Reference: Pharmacol Rep. 2012;64(3):739-44. https://pubmed.ncbi.nlm.nih.gov/22814027/
In vivo activity:
In dogs, i.v. difenidol preferentially enhanced vertebral over femoral arterial blood flow. Phenylephrine and potassium induced contraction of dog vertebral arterial rings, and difenidol inhibited this action. In addition, the L-type calcium channel blocker nifedipine, like difenidol, attenuated the potassium-induced contraction. These findings suggest that the difenidol-induced increase in vertebral arterial blood flow may be due to vascular relaxation mediated by mixed blocking actions at α(1)-adrenoceptors and voltage-gated calcium channel Ca(v)1.2. Reference: Eur J Pharmacol. 2012 Aug 15;689(1-3):165-71. https://pubmed.ncbi.nlm.nih.gov/22683869/
Solvent mg/mL mM
Solubility
DMF 50.0 144.55
DMSO 48.3 139.73
Ethanol 30.0 86.73
PBS (pH 7.2) 2.0 5.78
Water 14.8 42.89
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 345.91 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. Leung YM, Wong KL, Cheng KS, Kuo CS, Su TH, Chen YW, Cheng TH. Inhibition of voltage-gated K+ channels and Ca2+ channels by diphenidol. Pharmacol Rep. 2012;64(3):739-44. doi: 10.1016/s1734-1140(12)70869-1. PMID: 22814027. 2. Leung YM, Wu BT, Chen YC, Hung CH, Chen YW. Diphenidol inhibited sodium currents and produced spinal anesthesia. Neuropharmacology. 2010 Jun;58(7):1147-52. doi: 10.1016/j.neuropharm.2010.02.007. Epub 2010 Feb 20. PMID: 20176039. 3. Murakami K, Inoue N, Fuchikami C, Tajima K, Hashino A, Fukui H, Noda K, Oka M. Blockade of voltage-gated calcium channel Cav1.2 and α1-adrenoceptors increases vertebral artery blood flow induced by the antivertigo agent difenidol. Eur J Pharmacol. 2012 Aug 15;689(1-3):165-71. doi: 10.1016/j.ejphar.2012.05.046. Epub 2012 Jun 7. PMID: 22683869. 4. Andersson M, Aronsson P, Doufish D, Lampert A, Tobin G. Muscarinic receptor subtypes involved in urothelium-derived relaxatory effects in the inflamed rat urinary bladder. Auton Neurosci. 2012 Sep 25;170(1-2):5-11. doi: 10.1016/j.autneu.2012.06.004. Epub 2012 Jul 10. PMID: 22789737.
In vitro protocol:
1. Leung YM, Wong KL, Cheng KS, Kuo CS, Su TH, Chen YW, Cheng TH. Inhibition of voltage-gated K+ channels and Ca2+ channels by diphenidol. Pharmacol Rep. 2012;64(3):739-44. doi: 10.1016/s1734-1140(12)70869-1. PMID: 22814027. 2. Leung YM, Wu BT, Chen YC, Hung CH, Chen YW. Diphenidol inhibited sodium currents and produced spinal anesthesia. Neuropharmacology. 2010 Jun;58(7):1147-52. doi: 10.1016/j.neuropharm.2010.02.007. Epub 2010 Feb 20. PMID: 20176039.
In vivo protocol:
1. Murakami K, Inoue N, Fuchikami C, Tajima K, Hashino A, Fukui H, Noda K, Oka M. Blockade of voltage-gated calcium channel Cav1.2 and α1-adrenoceptors increases vertebral artery blood flow induced by the antivertigo agent difenidol. Eur J Pharmacol. 2012 Aug 15;689(1-3):165-71. doi: 10.1016/j.ejphar.2012.05.046. Epub 2012 Jun 7. PMID: 22683869. 2. Andersson M, Aronsson P, Doufish D, Lampert A, Tobin G. Muscarinic receptor subtypes involved in urothelium-derived relaxatory effects in the inflamed rat urinary bladder. Auton Neurosci. 2012 Sep 25;170(1-2):5-11. doi: 10.1016/j.autneu.2012.06.004. Epub 2012 Jul 10. PMID: 22789737.
1: Oritani S, Michiue T, Chen JH, Tani N, Ishikawa T. Biodistribution of diphenhydramine in reproductive organs in an overdose case. Hum Cell. 2017 Apr;30(2):106-116. doi: 10.1007/s13577-016-0151-9. Epub 2016 Nov 12. PubMed PMID: 27838883. 2: Wölfle U, Elsholz FA, Kersten A, Haarhaus B, Schumacher U, Schempp CM. Expression and Functional Activity of the Human Bitter Taste Receptor TAS2R38 in Human Placental Tissues and JEG-3 Cells. Molecules. 2016 Mar 3;21(3):306. doi: 10.3390/molecules21030306. PubMed PMID: 26950109. 3: Zhang L, Ma J, Li S, Xue R, Jin M, Zhou Y. Fatal diphenidol poisoning: a case report and a retrospective study of 16 cases. Forensic Sci Med Pathol. 2015 Dec;11(4):570-6. doi: 10.1007/s12024-015-9709-1. Epub 2015 Oct 19. PubMed PMID: 26481789. 4: Hirose N, Kawabata Y, Kawabata F, Nishimura S, Tabata S. Bitter taste receptor T2R1 activities were compatible with behavioral sensitivity to bitterness in chickens. Biochem Biophys Res Commun. 2015 May 1;460(2):464-8. doi: 10.1016/j.bbrc.2015.03.056. Epub 2015 Mar 19. PubMed PMID: 25796330. 5: Lin HT, Chiu CC, Wang JJ, Hung CH, Chen YW. High frequency transcutaneous electrical nerve stimulation with diphenidol administration results in an additive antiallodynic effect in rats following chronic constriction injury. Neurosci Lett. 2015 Mar 4;589:62-6. doi: 10.1016/j.neulet.2015.01.026. Epub 2015 Jan 14. PubMed PMID: 25596445. 6: Wölfle U, Elsholz FA, Kersten A, Haarhaus B, Müller WE, Schempp CM. Expression and functional activity of the bitter taste receptors TAS2R1 and TAS2R38 in human keratinocytes. Skin Pharmacol Physiol. 2015;28(3):137-46. doi: 10.1159/000367631. Epub 2015 Jan 7. PubMed PMID: 25573083. 7: Grazier MR, Armenian P, Vohra R. Illicit Distribution of Prescription Drugs: Report of Inadvertent Chloroquine Toxicity and a Market Survey of Businesses Serving Ethnic Minority Populations. Ann Pharmacother. 2014 Aug;48(8):1070-1076. Epub 2014 May 19. PubMed PMID: 24842857. 8: Li Y, Qi L, Shen Y, Ma H. Facile preparation of surface-exchangeable core@shell iron oxide@gold nanoparticles for magnetic solid-phase extraction: use of gold shell as the intermediate platform for versatile adsorbents with varying self-assembled monolayers. Anal Chim Acta. 2014 Feb 6;811:36-42. doi: 10.1016/j.aca.2013.12.020. Epub 2013 Dec 24. PubMed PMID: 24456592. 9: Grassin-Delyle S, Abrial C, Fayad-Kobeissi S, Brollo M, Faisy C, Alvarez JC, Naline E, Devillier P. The expression and relaxant effect of bitter taste receptors in human bronchi. Respir Res. 2013 Nov 22;14:134. doi: 10.1186/1465-9921-14-134. PubMed PMID: 24266887; PubMed Central PMCID: PMC4176101. 10: Chen YW, Tzeng JI, Liu KS, Yu SH, Hung CH, Wang JJ. Systemic diphenidol reduces neuropathic allodynia and TNF-alpha overexpression in rats after chronic constriction injury. Neurosci Lett. 2013 Sep 27;552:62-5. doi: 10.1016/j.neulet.2013.07.030. Epub 2013 Jul 31. PubMed PMID: 23916656. 11: Harper JN, Wright SH. Multiple mechanisms of ligand interaction with the human organic cation transporter, OCT2. Am J Physiol Renal Physiol. 2013 Jan 1;304(1):F56-67. doi: 10.1152/ajprenal.00486.2012. Epub 2012 Oct 3. PubMed PMID: 23034939; PubMed Central PMCID: PMC3971011. 12: Leung YM, Wong KL, Cheng KS, Kuo CS, Su TH, Chen YW, Cheng TH. Inhibition of voltage-gated K+ channels and Ca2+ channels by diphenidol. Pharmacol Rep. 2012;64(3):739-44. PubMed PMID: 22814027. 13: Andersson M, Aronsson P, Doufish D, Lampert A, Tobin G. Muscarinic receptor subtypes involved in urothelium-derived relaxatory effects in the inflamed rat urinary bladder. Auton Neurosci. 2012 Sep 25;170(1-2):5-11. doi: 10.1016/j.autneu.2012.06.004. Epub 2012 Jul 10. PubMed PMID: 22789737. 14: Murakami K, Inoue N, Fuchikami C, Tajima K, Hashino A, Fukui H, Noda K, Oka M. Blockade of voltage-gated calcium channel Cav1.2 and α1-adrenoceptors increases vertebral artery blood flow induced by the antivertigo agent difenidol. Eur J Pharmacol. 2012 Aug 15;689(1-3):165-71. doi: 10.1016/j.ejphar.2012.05.046. Epub 2012 Jun 7. PubMed PMID: 22683869. 15: Cao G, Liu Q, Huang Y, Li W, Yao S. Generation of gold nanostructures at the surface of platinum electrode by electrodeposition for ECL detection for CE. Electrophoresis. 2010 Mar;31(6):1055-62. doi: 10.1002/elps.200900433. PubMed PMID: 20309916. 16: Leung YM, Wu BT, Chen YC, Hung CH, Chen YW. Diphenidol inhibited sodium currents and produced spinal anesthesia. Neuropharmacology. 2010 Jun;58(7):1147-52. doi: 10.1016/j.neuropharm.2010.02.007. Epub 2010 Feb 20. PubMed PMID: 20176039. 17: Kitahara T, Kubo T, Okumura S, Kitahara M. Effects of endolymphatic sac drainage with steroids for intractable Meniere's disease: a long-term follow-up and randomized controlled study. Laryngoscope. 2008 May;118(5):854-61. doi: 10.1097/MLG.0b013e3181651c4a. PubMed PMID: 18520184. 18: Marcelín-Jiménez G, Morales-Martínez M, Angeles-Moreno AP, Mendoza-Morales L. Ultra-fast chromatographic micro-assay for quantification of diphenidol in plasma: application in an oral multi-dose switchability trial. Biomed Chromatogr. 2008 Oct;22(10):1143-8. doi: 10.1002/bmc.1037. PubMed PMID: 18506741. 19: Varoli L, Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M, Bedini A, Fazio N, Spampinato S. Diphenidol-related diamines as novel muscarinic M4 receptor antagonists. Bioorg Med Chem Lett. 2008 May 1;18(9):2972-6. doi: 10.1016/j.bmcl.2008.03.061. Epub 2008 Mar 23. PubMed PMID: 18395442. 20: Varoli L, Angeli P, Buccioni M, Burnelli S, Fazio N, Marucci G, Recanatini M, Spampinato S. Synthesis and pharmacological profile of a series of 1-substituted-2-carbonyl derivatives of Diphenidol: novel M4 muscarinic receptor antagonists. Med Chem. 2008 Mar;4(2):121-8. PubMed PMID: 18336331.