Tuaminoheptane

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
Clinical data
Trade namesHeptin, Heptadrine, Tuamine
Other namesTuamine; 2-Aminoheptane; 2-Heptanamine; 1-Methylhexylamine
ATC code
Identifiers
IUPAC name
  • Heptan-2-amine[1]
CAS Number
  • 123-82-0 Y
    6240-90-0 ((R)-isomer)
    44745-29-1 ((S)-isomer)
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.233
Chemical and physical data
FormulaC7H17N
Molar mass115.220 g·mol−1
3D model (JSmol)
Density0.766 g/mL g/cm3
SMILES
  • CCCCCC(C)N
InChI
  • InChI=1S/C7H17N/c1-3-4-5-6-7(2)8/h7H,3-6,8H2,1-2H3 Y
  • Key:VSRBKQFNFZQRBM-UHFFFAOYSA-N Y

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
  1. "tuamine - Compound Summary". USA: National Center for Biotechnology Information. 25 March 2005. Identification and Related Records. Retrieved 31 May 2012.
  2. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 623–. ISBN 978-1-4757-2085-3.
  3. I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 282–. ISBN 978-94-011-4439-1.
  4. NICKERSON M, DRESEL PE (1958). "Adrenergic drugs and their antagonists". Postgrad Med. 24 (3): 246–56. doi:10.1080/00325481.1958.11692208. PMID 13591086.
  5. Docherty JR (2008). "Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA)". Br. J. Pharmacol. 154 (3): 606–22. doi:10.1038/bjp.2008.124. PMC 2439527. PMID 18500382.
  6. Thevis M, Sigmund G, Geyer H, Schänzer W (2010). "Stimulants and doping in sport". Endocrinol. Metab. Clin. North Am. 39 (1): 89–105, ix. doi:10.1016/j.ecl.2009.10.011. PMID 20122452.
  7. Delicado EG, Fideu MD, Miras-Portugal MT, Pourrias B, Aunis D (1990). "Effect of tuamine, heptaminol and two analogues on uptake and release of catecholamines in cultured chromaffin cells". Biochem. Pharmacol. 40 (4): 821–5. doi:10.1016/0006-2952(90)90322-c. PMID 2386550.
  8. Schlessinger A, Geier E, Fan H, Irwin JJ, Shoichet BK, Giacomini KM, Sali A (2011). "Structure-based discovery of prescription drugs that interact with the norepinephrine transporter, NET". Proc. Natl. Acad. Sci. U.S.A. 108 (38): 15810–5. Bibcode:2011PNAS..10815810S. doi:10.1073/pnas.1106030108. PMC 3179104. PMID 21885739.
  9. Raoux M, Colomban C, Delmas P, Crest M (2007). "The amine-containing cutaneous irritant heptylamine inhibits the volume-regulated anion channel and mobilizes intracellular calcium in normal human epidermal keratinocytes". Mol. Pharmacol. 71 (6): 1685–94. doi:10.1124/mol.106.033324. PMID 17384225. S2CID 29565968.
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