Tuaminoheptane

Last updated
Tuaminoheptane
Tuaminoheptane.png
Clinical data
Trade names Heptin, Heptadrine, Tuamine
Other namesTuamine; 2-Aminoheptane; 2-Heptanamine; 1-Methylhexylamine
ATC code
Identifiers
  • Heptan-2-amine [1]
CAS Number
  • 123-82-0  Yes check.svgY
    6240-90-0 ((R)-isomer)
    44745-29-1 ((S)-isomer)
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.233 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C7H17N
Molar mass 115.220 g·mol−1
3D model (JSmol)
Density 0.766 g/mL g/cm3
  • CCCCCC(C)N
  • InChI=1S/C7H17N/c1-3-4-5-6-7(2)8/h7H,3-6,8H2,1-2H3 Yes check.svgY
  • Key:VSRBKQFNFZQRBM-UHFFFAOYSA-N Yes check.svgY

Tuaminoheptane (INN Tooltip International Nonproprietary Name, BAN Tooltip British Approved Name; brand names Heptin, Heptadrine, Tuamine; also known as tuamine and 2-aminoheptane) is a sympathomimetic agent and vasoconstrictor which is used as a nasal decongestant. [2] [3] [4] It has also been used as a stimulant. [5] [6]

Contents

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 on the 2011 list of prohibited substances published by the World Anti-Doping Agency. [5]

See also

References

  1. ↑ "tuamine - Compound Summary". PubChem. USA: National Center for Biotechnology Information. 25 March 2005. Identification and Related Records. Retrieved 31 May 2012.
  2. ↑ 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.
  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.
  4. ↑ 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.
  5. 1 2 Docherty 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.
  6. 1 2 3 Thevis 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.
  7. ↑ 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.
  8. 1 2 Schlessinger 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.
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