Critical Thinking/Writing Assignment # 1 LASC 636 - Principles of Toxicology Distributed: January 21, 2014 Due: February 4, 2014 Common/Trade

Name(s): Orajel For immediate toothache pain relief most adults (individuals 12+) look for over the counter topical remedies such as Orajel. Chemical Name(s): Benzocaine, Ethyl p-aminobenzoate

Benzocaine (ethyl amino benzoate) is a white crystalline ester commonly used as a topical pain reliever in many over-the-counter analgesic products (Oxford Dictionaries, 2014). Chemical Formula: C9H12CINO2 (Gupta et al, 2000) Molecular Weight: 165.19 g/mol (Sweetman, 2007) Boiling/Freezing Point: 310C (590F)/ 89C (192.2F) (Sweetman, 2007) Vapor Pressure: 00018/crystalline, 00083/liquid (Gobble et al., 2013) Solubility: Soluble in methanol, diethyl ether. Very slightly soluble in cold water. (Gobble et al., 2013) Manufacturer(s) or Source: Church & Dwight (http://www.orajel.com/) Discovery of Chemical: Environmental Fate/Half-Life: 55 mins. (Gupta et al, 2000) LD50s (Oral, Dermal & Inhalational): Bird (wild), with reported dose 56mg/kg (56mg/kg) (oral) ( Schafer, 1972) Mouse, 216mg/kg (216mg/kg) (oral) (Fitzgerald et al., 1974) Rat, 3040 mg/kg (oral) (Vestnik,1996) rabbit, 1150mg/kg (1150mg/kg) (oral) (Drugs in Japan,1982)

LC50s: Acute Toxicity: In humans a disease known as methemoglobinemia from oral, rectal and dermal exposures has been seen. There is disagreement whether this is an idiosyncratic event or a dose-related event. No LD50 recorded. (Spiller, 2000)

Literature Cited: Benzocaine. Oxford Dictionaires Web 3 Feb 2014 www.http://oxforddictionaries.com/definition/american_english/benzocaine Schafer, E. (1972) Toxicology and Applied Pharmacology. Vol. 21, Pg. 315. Fitzgerald, T.J., Doull, J., and DeFeo, F.G. (1974) Radioprotective activity of p-aminopropiophenone. Structure-activity investigation. Journal of Medicinal Chemistry, Vol 17, Pg. 900. Vestnik, T.T. (1996) (18-20 Vadkovskii per. Moscow, 101479, Russia) Vol.2 ,34. Sweetman, S.C., ed. Martindale (2007)The Complete Drug Reference. 35th ed. London, England: Pharmaceutical Press; 1808-1812. Gobble, C., Gutterman, A., Chickos, J.S. (2013) Some thermodynamic properties of benzocaine. Structural Chemistry. Vol. 24 1903-1907. Spiller, H.A. (2000) Vet Hum Toxicolog. Vol. 42 (4): 228-31. Gupta, P.M.,. Lala, D.S., Arsura, E.L. (2000) Benzocaine-Induced Methemoglobinemia. Southern Medical Journal 93(1). Drugs in Japan Vol. 6, Pg. 33, 1982. http://www.orajel.com/ Accessed 31 February 2014 Klein, S.L., Nustad, R.A., Feinberg, S.E., Fonseca, R.J.(1983) Acute toxic methemoglobinemia caused by a topical anesthetic. The American Academy of Pedodontics Vol. 5 (2)107-108.