Diphenylpyraline hydrochloride | CAS#132-18-3 |

MedKoo Cat#: 591255 | Name: Diphenylpyraline hydrochloride

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Description:

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

Diphenylpyraline hydrochloride is a first-generation antihistamine with anticholinergic effects of the diphenylpiperidine class.

Chemical Structure

Diphenylpyraline hydrochloride

CAS#132-18-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 591255

Name: Diphenylpyraline hydrochloride

CAS#: 132-18-3 (HCl)

Chemical Formula: C19H24ClNO

Exact Mass: 317.1546

Molecular Weight: 317.86

Elemental Analysis: C, 71.80; H, 7.61; Cl, 11.15; N, 4.41; O, 5.03

Price and Availability

Size	Price	Availability	Quantity
10g	USD 350.00	2 Weeks

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Related CAS #

147-20-6 (free base) 132-18-3 (HCl)

Synonym

Diphenylpyraline hydrochloride; Diafen hydrochloride; Diaphen; Diphenylpyraline HCl; Allerzine; NSC 61825; NSC61825; NSC-61825

IUPAC/Chemical Name

Piperidine, 4-(diphenylmethoxy)-1-methyl-, hydrochloride

InChi Key

LPRLDRXGWKXRMQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H23NO.ClH/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17;/h2-11,18-19H,12-15H2,1H3;1H

SMILES Code

CN1CCC(OC(C2=CC=CC=C2)C3=CC=CC=C3)CC1.[H]Cl

Appearance

Solid powder

Purity

>95% (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:

Diphenylpyraline hydrochloride is a potent histamine H1 receptor antagonist.

In vitro activity:

TBD

In vivo activity:

Maximal dopamine uptake inhibition was observed 40 min after DPP (diphenylpyraline) and 30 min after cocaine administration. Post hoc tests revealed that DPP exhibited a prolonged effect on dopamine uptake inhibition in comparison to cocaine. DPP treated mice showed a significantly higher apparent Km after 40 (t=3.275; P<0.01), 50 (t=4.473; P<0.01) and 60 (t=4.699; P<0.01) min in comparison to cocaine treated mice. Reference: Eur J Pharmacol. 2012 May 15;683(1-3):161-5. https://pubmed.ncbi.nlm.nih.gov/22445882/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	314.61
	Water	100.0	314.61

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 317.86 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.

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. Oleson EB, Ferris MJ, España RA, Harp J, Jones SR. Effects of the histamine H₁ receptor antagonist and benztropine analog diphenylpyraline on dopamine uptake, locomotion and reward. Eur J Pharmacol. 2012 May 15;683(1-3):161-5. doi: 10.1016/j.ejphar.2012.03.003. Epub 2012 Mar 15. PMID: 22445882; PMCID: PMC3340496. 2. Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR. Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. doi: 10.1016/j.ejphar.2004.11.017. Epub 2004 Dec 8. PMID: 15627433.

In vitro protocol:

TBD

In vivo protocol:

1: Dinis-Oliveira RJ. Metabolomics of methadone: clinical and forensic toxicological implications and variability of dose response. Drug Metab Rev. 2016 Nov;48(4):568-576. Epub 2016 Jun 20. Review. PubMed PMID: 27320437. 2: Pulgar VM, Keith Harp J. Vascular effects of diphenylmethoxypiperidine-derived dopamine uptake inhibitors. Bioorg Med Chem Lett. 2014 Jun 1;24(11):2429-32. doi: 10.1016/j.bmcl.2014.04.040. Epub 2014 Apr 18. PubMed PMID: 24792462; PubMed Central PMCID: PMC4056188. 3: Wentworth AB, Yiannias JA, Keeling JH, Hall MR, Camilleri MJ, Drage LA, Torgerson RR, Fett DD, Prakash AV, Scalf LA, Allen EM, Johnson JS, Singh N, Nordberg Linehan DL, Killian JM, Davis MD. Trends in patch-test results and allergen changes in the standard series: a Mayo Clinic 5-year retrospective review (January 1, 2006, to December 31, 2010). J Am Acad Dermatol. 2014 Feb;70(2):269-75.e4. doi: 10.1016/j.jaad.2013.09.047. Epub 2013 Nov 20. PubMed PMID: 24268786. 4: Oleson EB, Ferris MJ, España RA, Harp J, Jones SR. Effects of the histamine H₁ receptor antagonist and benztropine analog diphenylpyraline on dopamine uptake, locomotion and reward. Eur J Pharmacol. 2012 May 15;683(1-3):161-5. doi: 10.1016/j.ejphar.2012.03.003. Epub 2012 Mar 15. PubMed PMID: 22445882; PubMed Central PMCID: PMC3340496. 5: Montijo-Barrios E, Cadena F, Ramírez-Mayans JA, Gutiérrez-Castrellón P. [Clinical trial on the effect of buphenine, aminophenazone and diphenylpyraline hydrochloride in treating the common cold in children of 6 to 24 months of age]. Rev Invest Clin. 2011 Jul-Aug;63(4):335-43. Spanish. PubMed PMID: 22364032. 6: Feás X, Ye L, Hosseini SV, Fente CA, Cepeda A. Development and validation of LC-MS/MS method for the determination of cyproheptadine in several pharmaceutical syrup formulations. J Pharm Biomed Anal. 2009 Dec 5;50(5):1044-9. doi: 10.1016/j.jpba.2009.06.006. Epub 2009 Jun 12. PubMed PMID: 19574011. 7: Feás X, Ye L, Regal P, Fente CA, Hosseini SV, Cepeda A. Application of dummy molecularly imprinted solid-phase extraction in the analysis of cyproheptadine in bovine urine. J Sep Sci. 2009 May;32(10):1740-7. doi: 10.1002/jssc.200800726. PubMed PMID: 19472275. 8: Fente CA, Regal P, Vázquez BI, Feás X, Franco CM, Cepeda A. Development and validation of an LC-MS/MS confirmatory method for residue analysis of cyproheptadine in urine of food-producing animals. J Agric Food Chem. 2009 Mar 25;57(6):2595-8. doi: 10.1021/jf803395r. PubMed PMID: 19231896. 9: Weis R, Schweiger K, Faist J, Rajkovic E, Kungl AJ, Fabian WM, Schunack W, Seebacher W. Antimycobacterial and H1-antihistaminic activity of 2-substituted piperidine derivatives. Bioorg Med Chem. 2008 Dec 15;16(24):10326-31. doi: 10.1016/j.bmc.2008.10.042. Epub 2008 Oct 22. PubMed PMID: 18977145. 10: Weis R, Faist J, di Vora U, Schweiger K, Brandner B, Kungl AJ, Seebacher W. Antimycobacterial activity of diphenylpyraline derivatives. Eur J Med Chem. 2008 Apr;43(4):872-9. Epub 2007 Jul 10. PubMed PMID: 17714832. 11: Shakleya DM, Jansson LM, Huestis MA. Validation of a LC-APCI-MS/MS method for quantification of methadone, 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine (EDDP) and 2-ethyl-5-methyl-3,3-diphenylpyraline (EMDP) in infant plasma following protein precipitation. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Sep 1;856(1-2):267-72. Epub 2007 Jun 16. PubMed PMID: 17602899. 12: Hasegawa C, Kumazawa T, Lee XP, Fujishiro M, Kuriki A, Marumo A, Seno H, Sato K. Simultaneous determination of ten antihistamine drugs in human plasma using pipette tip solid-phase extraction and gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(4):537-43. PubMed PMID: 16419026. 13: Choo RE, Murphy CM, Jones HE, Huestis MA. Determination of methadone, 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, 2-ethyl-5-methyl-3,3-diphenylpyraline and methadol in meconium by liquid chromatography atmospheric pressure chemical ionization tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jan 25;814(2):369-73. PubMed PMID: 15639461. 14: Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR. Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. Epub 2004 Dec 8. PubMed PMID: 15627433. 15: Bacon NJ, Oni O, White RA. Treatment of urethral sphincter mechanism incompetence in 11 bitches with a sustained-release formulation of phenylpropanolamine hydrochloride. Vet Rec. 2002 Sep 28;151(13):373-6. PubMed PMID: 12403516. 16: Oda Y, Kharasch ED. Metabolism of methadone and levo-alpha-acetylmethadol (LAAM) by human intestinal cytochrome P450 3A4 (CYP3A4): potential contribution of intestinal metabolism to presystemic clearance and bioactivation. J Pharmacol Exp Ther. 2001 Sep;298(3):1021-32. PubMed PMID: 11504799. 17: Ishii A, Kurihara R, Watanabe-Suzuki K, Kumazawa T, Seno H, Matsushima H, Suzuki O, Katsumata Y. Sensitive determination of pethidine in body fluids by surface ionization organic mass spectrometry. J Chromatogr B Biomed Sci Appl. 2001 Jul 5;758(1):117-21. PubMed PMID: 11482730. 18: Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I. Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients. J Neurol Sci. 2001 Jan 1;182(2):95-7. PubMed PMID: 11137513. 19: Vasudevan M, Ravisankar S, Sathiyanarayanan A, Chandan RS. Simultaneous estimation of phenylpropanolamine HCl, guaiphenesin and diphenylpyraline HCl in syrups by LC. J Pharm Biomed Anal. 2000 Dec;24(1):25-31. PubMed PMID: 11108536. 20: San Andrés MP, Sicilia D, Rubio S, Pérez-Bendito D. Determination of antihistamines based on the formation of mixed aggregates with surfactants. Analyst. 1998 May;123(5):1079-84. PubMed PMID: 9709492.