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Tuaminoheptane

From Wikipedia, the free encyclopedia
Sympathomimetic agent
Pharmaceutical compound
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)
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.004.233Edit 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 namesHeptin,Heptadrine,Tuamine; also known astuamine and2-aminoheptane) is asympathomimetic agent andvasoconstrictor which was formerly used as anasal decongestant.[2][3][4] It is still used in France as a nasal decongestant but its use is not recommended by the health authorities due to the lack of evidence of its effectiveness. It has also been used as astimulant.[5][6]

Tuaminoheptane has been found to act as areuptake inhibitor andreleasing agent ofnorepinephrine, which may underlie its decongestant and stimulant effects.[7][8][6] It is analkylamine.[6] Thechemical structure of the drug differs from that of othernorepinephrine releasing agents, such as thephenethylamines, which, in contrast to tuaminoheptane, have anaromatic ring in their structure.[8] Tuaminoheptane is also askin irritant and can causecontact dermatitis viainhibition ofvolume-regulated anion channels, which limits its usefulness as a decongestant.[9]

Tuaminoheptane is on the 2011 list of prohibited substances published by theWorld 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. Retrieved31 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. ^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.
  6. ^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.
  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. ^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.
  9. ^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.

External links

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Decongestants and other nasal preparations (R01)
Topical
Sympathomimetics, plain
Antiallergic agents,
excluding corticosteroids
Corticosteroids
Other nasal preparations
Combination products
Systemic use:
Sympathomimetics
Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
Cathinones
Cholinergics
Convulsants
Eugeroics
Oxazolines
Phenethylamines
Phenylmorpholines
Piperazines
Piperidines
Pyrrolidines
Racetams
Tropanes
Tryptamines
Others
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
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