Abstract
Aromatic vapors of monoterpenoids such as menthol and camphor are known to possess antitussive effects for the symptomatic relief of upper respiratory tract. The lactams 10 and 11 of menthol and camphor, respectively, have been synthesised and evaluated first time for their antitussive activity in citric acid-induced cough in guinea pig model. The effect of nitrogen insertion in the chemical architecture of menthol and camphor on the antitussive activity was reflected by the significant decrease of the cough frequency and increase in the cough latency exhibited by aerosolized 10 and 11. Prior exposure of aerolsolised 10 for 5 min at different concentrations (15, 30, and 60 μg/l) significantly reduced cough response induced by citric acid and also increased latency to initial cough response. Similarly 11 has showed greater inhibitory cough response in comparison to camphor at concentrations such as 125, 250, and 500 μg/l. However, latency to initial cough response was only increased at the concentrations of 250 and 500 μg/l.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Burt CW, Schappert SM (2004) Ambulatory care visits to physician offices, hospital outpatient departments, and emergency departments: United States, 1999–2000. Vital Health Stat 13(157):1–70
Fendrick AM, Monto AS, Nightengale B, Sarnes M (2003) The economic burden of non- influenza-related viral respiratory tract infection in the United States. Arch Intern Med 163:487–494
Fox AJ (1996) Modulation of cough and airway sensory fibres. Pulm Pharmacol 9:335–342
French CL, Irwin RS, Curly FJ, Krikorian CJ (1998) Impact of chronic cough on quality of life. Arch Intern Med 158:1657–1661
Hensel H, Zotterman Y (1951) The effect of menthol on the thermal receptors. Acta Physiol Scand 24:27–34
Krow GR, Szczepanski S (1980) Unusual regiochemistry in a Beckmann like rearrangement of camphor. α-camphidone via methylene migration. Tetrahedron Lett 21:4593–4596
Laude EA, Morice AH, Grattan TJ (1994) The antitussive effects of menthol, camphor and cineole in conscious guinea-pigs. Pulm Pharmacology 7:179–184
Lee KK, Birring SS (2010) Cough and sleep. Lung 188(Suppl 1):S91–S94
Lin LG, Ho Leung HP, Zhu JY, Tang CP, Ke CQ, Rudd JA, Lin G, Ye Y (2008) Croomine- and tuberostemonine-type alkaloids from roots of Stemona tuberose and their antitussive activity. Tetrahedron 64:10155–10161
Lochynski S, Kuldo J, Frackwiak B, Holband J, Wojcik G (2000) Stereochemistry of terpene derivatives. Part 2:1 Synthesis of new chiral amino acids with potential neuroactivity. Tetrahedron Asymmetr 11:1295–1302
Morice AH, Marshall AE, Higgins KS, Grattan TJ (1994) Effect of inhaled menthol on citric acid induced cough in normal subjects. Thorax 49:1024–1026
Packman EW, London S (1980) The utility of artificially cough as a clinical model for evaluating the antitussive effects of aromatics delivered by inunction. Eur Resp J 61(110):101–109
Paul IM, Beiler J, McMonagle A, Shaffer ML, Duda L, Berlin CM Jr (2004) Effect of dextromethorphan, diphenhydramine, and placebo on nocturnal cough and sleep quality for coughing children and their parents. Pediatrics 114(1):e85–e90
Schappert SM (1997) Ambulatory care visits to physician offices, hospital outpatient departments, and emergency: United States, 1995. National Center for Health Statistics. Vital Health Stat 13(129)
Swandulla D, Carbone E, Schafer K, Lux HD (1987) Effect of menthol on 2 types of Ca currents in cultured sensory neurones of vertebrates. Eur J Physiol 409:52–59
Takahashi N, Mochizuki D (1997) Azepine derivatives and use thereof. U S Patent (App. no. 413285), 19 Aug 1997
Acknowledgments
The authors wish to thank Mr. Parveen Garg, Chairman of the ISF College of Pharmacy Moga, Punjab for providing the support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kumar, N., Nepali, K., Sapra, S. et al. Effect of nitrogen insertion on the antitussive properties of menthol and camphor. Med Chem Res 21, 531–537 (2012). https://doi.org/10.1007/s00044-011-9560-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-011-9560-1