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1 See also  





2 References  





3 External links  














Tuaminoheptane






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Tuaminoheptane
Clinical data
Trade namesHeptin, Heptadrine, Tuamine
Other namesTuamine; 2-Aminoheptane; 2-Heptanamine; 1-Methylhexylamine
ATC code
Identifiers
  • Heptan-2-amine[1]

CAS Number
  • 123-82-0 checkY
    6240-90-0 ((R)-isomer)
    44745-29-1 ((S)-isomer)
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.233 Edit this at Wikidata
Chemical and physical data
FormulaC7H17N
Molar mass115.220 g·mol−1
3D model (JSmol)
Density0.766 g/mL g/cm3
  • CCCCCC(C)N

  • InChI=1S/C7H17N/c1-3-4-5-6-7(2)8/h7H,3-6,8H2,1-2H3 checkY

  • Key:VSRBKQFNFZQRBM-UHFFFAOYSA-N checkY

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 agentofnorepinephrine, 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 inhibitionofvolume-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

[edit]

References

[edit]
  1. ^ "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.
  • ^ a b 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.
  • ^ a b c 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.
  • ^ 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.
  • ^ a b 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.
  • ^ 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.
  • [edit]
    Retrieved from "https://en.wikipedia.org/w/index.php?title=Tuaminoheptane&oldid=1191595337"

    Categories: 
    Abandoned drugs
    Alkylamines
    Decongestants
    Ion channel blockers
    Norepinephrine releasing agents
    Stimulants
    Hidden categories: 
    Articles with short description
    Short description is different from Wikidata
    ECHA InfoCard ID from Wikidata
    Chemical pages without DrugBank identifier
    Drugs with no legal status
    Articles containing unverified chemical infoboxes
    Webarchive template wayback links
     



    This page was last edited on 24 December 2023, at 13:37 (UTC).

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