Chemistry:Tuaminoheptane
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| Trade names | Heptin, Heptadrine, Tuamine |
| Other names | Tuamine; 2-Aminoheptane; 2-Heptanamine; 1-Methylhexylamine |
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| Formula | C7H17N |
| Molar mass | 115.220 g·mol−1 |
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| Density | 0.766 g/mL g/cm3 |
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Tuaminoheptane (INN, BAN; 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]
See also
References
- ↑ "tuamine - Compound Summary". PubChem. USA: National Center for Biotechnology Information. 25 March 2005. Identification and Related Records. https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5603&loc=ec_rcs#x291.
- ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 623–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA623.
- ↑ Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. pp. 282–. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA282.
- ↑ "Adrenergic drugs and their antagonists". Postgraduate Medicine 24 (3): 246–256. September 1958. doi:10.1080/00325481.1958.11692208. PMID 13591086.
- ↑ 5.0 5.1 "Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA)". British Journal of Pharmacology 154 (3): 606–622. June 2008. doi:10.1038/bjp.2008.124. PMID 18500382.
- ↑ 6.0 6.1 6.2 "Stimulants and doping in sport". Endocrinology and Metabolism Clinics of North America 39 (1): 89–105, ix. March 2010. doi:10.1016/j.ecl.2009.10.011. PMID 20122452.
- ↑ "Effect of tuamine, heptaminol and two analogues on uptake and release of catecholamines in cultured chromaffin cells". Biochemical Pharmacology 40 (4): 821–825. August 1990. doi:10.1016/0006-2952(90)90322-c. PMID 2386550.
- ↑ 8.0 8.1 "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. September 2011. doi:10.1073/pnas.1106030108. PMID 21885739. Bibcode: 2011PNAS..10815810S.
- ↑ "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. June 2007. doi:10.1124/mol.106.033324. PMID 17384225.
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