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MedKoo Cat#: 317623 | Name: Diphenhydramine
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Description:

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

Diphenhydramine is a first-generation antihistamine possessing anticholinergic, antitussive, antiemetic, and sedative properties that is mainly used to treat allergies. It is also used in the management of drug-induced parkinsonism and other extrapyramidal symptoms.

Chemical Structure

Diphenhydramine
Diphenhydramine
CAS#58-73-1 (free base)

Theoretical Analysis

MedKoo Cat#: 317623

Name: Diphenhydramine

CAS#: 58-73-1 (free base)

Chemical Formula: C17H21NO

Exact Mass: 255.1623

Molecular Weight: 255.35

Elemental Analysis: C, 79.96; H, 8.29; N, 5.49; O, 6.27

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 weeks
10g USD 400.00 2 Weeks
25g USD 750.00 2 weeks
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Related CAS #
88637-37-0 (citrate) 147-24-0 (HCl) 58-73-1 (free base) 7491-10-3 (salicylate)
Synonym
PM 255; PM255; PM-255; Diphenhydramine; Dabylen; Debendrin; Difenhydramine.
IUPAC/Chemical Name
2-(benzhydryloxy)-N,N-dimethylethanamine
InChi Key
ZZVUWRFHKOJYTH-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3
SMILES Code
CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2
Appearance
Liquid
Purity
>96% (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, not in water
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:
Diphenhydramine is a first-generation histamine H1-receptor antagonist with anti-cholinergic effect. Diphenhydramine hydrochloride can across the ovine blood-brain barrier (BBB).
In vitro activity:
Exogenous histamine did not alter the proliferation or viability of these cells. In contrast, diphenhydramine induced apoptosis in a dose- and time-dependent manner in both cell lines, whereas cimetidine failed to induce significant effects at similar concentrations. Diphenhydramine-induced apoptosis was evaluated in terms of morphology, flow cytometry, and the release of cytochrome c to the cytosol. Reference: Oncol Res. 2004;14(7-8):363-72. https://pubmed.ncbi.nlm.nih.gov/15301427/
In vivo activity:
Results of the study suggest that DPM (diphenhydramine) causes reduction in CE and prevents neuronal degeneration. It also causes reduction in inflammation and oxidative stress in a dose-dependent manner. The level of Bax was found to be elevated, together with reduction in the Bcl-2 level in the DPM-treated rat group. Reference: Pharmacology. 2020;105(1-2):47-53. https://pubmed.ncbi.nlm.nih.gov/31553997/

Preparing Stock Solutions

The following data is based on the product molecular weight 255.35 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
Formulation protocol:
1. Hamano H, Ikeda Y, Goda M, Fukushima K, Kishi S, Chuma M, Yamashita M, Niimura T, Takechi K, Imanishi M, Zamami Y, Horinouchi Y, Izawa-Ishizawa Y, Miyamoto L, Ishizawa K, Fujino H, Tamaki T, Aihara KI, Tsuchiya K. Diphenhydramine may be a preventive medicine against cisplatin-induced kidney toxicity. Kidney Int. 2021 Apr;99(4):885-899. doi: 10.1016/j.kint.2020.10.041. Epub 2020 Dec 9. PMID: 33307103. 2. Jangi SM, Asumendi A, Arlucea J, Nieto N, Perez-Yarza G, Morales MC, de la Fuente-Pinedo M, Boyano MD. Apoptosis of human T-cell acute lymphoblastic leukemia cells by diphenhydramine, an H1 histamine receptor antagonist. Oncol Res. 2004;14(7-8):363-72. doi: 10.3727/0965040041292369. PMID: 15301427. 3. Pan W, Cao Z, Liu D, Jiao Y. Protective Effect of Diphenhydramine against Traumatic Brain Injury in Rats via Modulation of Oxidative Stress and Inflammation. Pharmacology. 2020;105(1-2):47-53. doi: 10.1159/000502767. Epub 2019 Sep 25. PMID: 31553997. 4. Or CR, Su HL, Lee WC, Yang SY, Ho C, Chang CC. Diphenhydramine induces melanoma cell apoptosis by suppressing STAT3/MCL-1 survival signaling and retards B16-F10 melanoma growth in vivo. Oncol Rep. 2016 Dec;36(6):3465-3471. doi: 10.3892/or.2016.5201. Epub 2016 Oct 25. PMID: 27779705.
In vitro protocol:
1. Hamano H, Ikeda Y, Goda M, Fukushima K, Kishi S, Chuma M, Yamashita M, Niimura T, Takechi K, Imanishi M, Zamami Y, Horinouchi Y, Izawa-Ishizawa Y, Miyamoto L, Ishizawa K, Fujino H, Tamaki T, Aihara KI, Tsuchiya K. Diphenhydramine may be a preventive medicine against cisplatin-induced kidney toxicity. Kidney Int. 2021 Apr;99(4):885-899. doi: 10.1016/j.kint.2020.10.041. Epub 2020 Dec 9. PMID: 33307103. 2. Jangi SM, Asumendi A, Arlucea J, Nieto N, Perez-Yarza G, Morales MC, de la Fuente-Pinedo M, Boyano MD. Apoptosis of human T-cell acute lymphoblastic leukemia cells by diphenhydramine, an H1 histamine receptor antagonist. Oncol Res. 2004;14(7-8):363-72. doi: 10.3727/0965040041292369. PMID: 15301427.
In vivo protocol:
1. Pan W, Cao Z, Liu D, Jiao Y. Protective Effect of Diphenhydramine against Traumatic Brain Injury in Rats via Modulation of Oxidative Stress and Inflammation. Pharmacology. 2020;105(1-2):47-53. doi: 10.1159/000502767. Epub 2019 Sep 25. PMID: 31553997. 2. Or CR, Su HL, Lee WC, Yang SY, Ho C, Chang CC. Diphenhydramine induces melanoma cell apoptosis by suppressing STAT3/MCL-1 survival signaling and retards B16-F10 melanoma growth in vivo. Oncol Rep. 2016 Dec;36(6):3465-3471. doi: 10.3892/or.2016.5201. Epub 2016 Oct 25. PMID: 27779705.
1: Abdi A, Rose E, Levine M. Diphenhydramine overdose with intraventricular conduction delay treated with hypertonic sodium bicarbonate and i.v. lipid emulsion. West J Emerg Med. 2014 Nov;15(7):855-8. doi: 10.5811/westjem.2014.8.23407. Epub 2014 Sep 19. Review. PubMed PMID: 25493135; PubMed Central PMCID: PMC4251236. 2: Erbe S, Bschor T. [Diphenhydramine addiction and detoxification. A systematic review and case report]. Psychiatr Prax. 2013 Jul;40(5):248-51. doi: 10.1055/s-0032-1332949. Epub 2013 Mar 4. Review. German. PubMed PMID: 23459952. 3: [Current topics and problems in toxicology laboratories--7: Occurrence of poisoning due to 15 chemicals and introduction of analytical methods for diphenhydramine and SSRIs]. Chudoku Kenkyu. 2010 Jun;23(2):124-8. Review. Japanese. PubMed PMID: 20593650. 4: Björnsdóttir I, Einarson TR, Gudmundsson LS, Einarsdóttir RA. Efficacy of diphenhydramine against cough in humans: a review. Pharm World Sci. 2007 Dec;29(6):577-83. Epub 2007 May 8. Review. PubMed PMID: 17486423. 5: Nine JS, Rund CR. Fatality from diphenhydramine monointoxication: a case report and review of the infant, pediatric, and adult literature. Am J Forensic Med Pathol. 2006 Mar;27(1):36-41. Review. PubMed PMID: 16501346. 6: Cox D, Ahmed Z, McBride AJ. Diphenhydramine dependence. Addiction. 2001 Mar;96(3):516-7. Review. PubMed PMID: 11310441. 7: Lang K, Sigusch H, Müller S. [An anticholinergic syndrome with hallucinatory psychosis after diphenhydramine poisoning]. Dtsch Med Wochenschr. 1995 Dec 8;120(49):1695-8. Review. German. PubMed PMID: 7497894. 8: Chan CY, Wallander KA. Diphenhydramine toxicity in three children with varicella-zoster infection. DICP. 1991 Feb;25(2):130-2. Review. PubMed PMID: 2058184. 9: Banerji A, Long AA, Camargo CA Jr. Diphenhydramine versus nonsedating antihistamines for acute allergic reactions: a literature review. Allergy Asthma Proc. 2007 Jul-Aug;28(4):418-26. Review. PubMed PMID: 17883909. 10: Geiger TL, Howard SC. Acetaminophen and diphenhydramine premedication for allergic and febrile nonhemolytic transfusion reactions: good prophylaxis or bad practice? Transfus Med Rev. 2007 Jan;21(1):1-12. Review. PubMed PMID: 17174216; PubMed Central PMCID: PMC1868404. 11: Green SM. What is the role of diphenhydramine in local anesthesia? Acad Emerg Med. 1996 Mar;3(3):198-200. Review. PubMed PMID: 8673772.

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