Tuaminoheptane (INNTooltip International Nonproprietary Name, BANTooltip British Approved Name; brand names Heptin, Heptadrine, Tuamine; also known as tuamine and 2-aminoheptane) is a sympathomimetic agent and vasoconstrictor which was formerly used as a nasal decongestant.[2][3][4] It has also been used as a stimulant.[5][6]
Tuaminoheptane has been found to act as a reuptake inhibitor and releasing agent of norepinephrine, which may underlie its decongestant and stimulant effects.[7][8][6] It is an alkylamine.[6] The chemical structure of the drug differs from that of other norepinephrine releasing agents, such as the phenethylamines, which, in contrast to tuaminoheptane, have an aromatic ring in their structure.[8] Tuaminoheptane is also a skin irritant and can cause contact dermatitis via inhibition of volume-regulated anion channels, which limits its usefulness as a decongestant.[9]
Tuaminoheptane is on the 2011 list of prohibited substances published by the World Anti-Doping Agency.[5]
^"tuamine - Compound Summary". PubChem. USA: National Center for Biotechnology Information. 25 March 2005. Identification and Related Records. Retrieved 31 May 2012.
^Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 623–. ISBN 978-1-4757-2085-3.
^Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 282–. ISBN 978-94-011-4439-1.
^Nickerson M, Dresel PE (September 1958). "Adrenergic drugs and their antagonists". Postgraduate Medicine. 24 (3): 246–256. doi:10.1080/00325481.1958.11692208. PMID 13591086.
^ abDocherty JR (June 2008). "Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA)". British Journal of Pharmacology. 154 (3): 606–622. doi:10.1038/bjp.2008.124. PMC 2439527. PMID 18500382.
^ abcThevis M, Sigmund G, Geyer H, Schänzer W (March 2010). "Stimulants and doping in sport". Endocrinology and Metabolism Clinics of North America. 39 (1): 89–105, ix. doi:10.1016/j.ecl.2009.10.011. PMID 20122452.
^Delicado EG, Fideu MD, Miras-Portugal MT, Pourrias B, Aunis D (August 1990). "Effect of tuamine, heptaminol and two analogues on uptake and release of catecholamines in cultured chromaffin cells". Biochemical Pharmacology. 40 (4): 821–825. doi:10.1016/0006-2952(90)90322-c. PMID 2386550.
^ abSchlessinger A, Geier E, Fan H, Irwin JJ, Shoichet BK, Giacomini KM, Sali A (September 2011). "Structure-based discovery of prescription drugs that interact with the norepinephrine transporter, NET". Proceedings of the National Academy of Sciences of the United States of America. 108 (38): 15810–15815. Bibcode:2011PNAS..10815810S. doi:10.1073/pnas.1106030108. PMC 3179104. PMID 21885739.
^Raoux M, Colomban C, Delmas P, Crest M (June 2007). "The amine-containing cutaneous irritant heptylamine inhibits the volume-regulated anion channel and mobilizes intracellular calcium in normal human epidermal keratinocytes". Molecular Pharmacology. 71 (6): 1685–1694. doi:10.1124/mol.106.033324. PMID 17384225. S2CID 29565968.
Tuaminoheptane (INNTooltip International Nonproprietary Name, BANTooltip British Approved Name; brand names Heptin, Heptadrine, Tuamine; also known as...
the silver medal, but was disqualified after he tested positive for Tuaminoheptane. a Swimmers who participated in the heats only and received medals....
Misha Aloyan of Russia, was disqualified after testing positive for tuaminoheptane. 1904: 115–125 lb (52.2–56.7 kg) 1908: 116–126 lb (52.6–57.2 kg) 1920–1928:...
methylhexamine, 1,3-dimethylamylamine, 1,3-DMAA, dimethylamylamine, and DMAA) Tuaminoheptane This set index page lists chemical structure articles associated with...
the silver medal, but was disqualified after he tested positive for Tuaminoheptane. * Host nation (Brazil) A report published in 2021 into the judging...
compounds Related alkanamines Pentylamine Cadaverine Methylhexanamine Tuaminoheptane Except where otherwise noted, data are given for materials in their...
four other similar compounds being brought to market for that use: tuaminoheptane, octin (isometheptene), oenethyl (2-methylaminoheptane), and propylhexedrine;...
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