Heptaminol

Heptaminol
Names
IUPAC name
(RS)-6-Amino-2-methylheptan-2-ol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.144
EC Number
  • 206-758-0
MeSH Heptaminol
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H19NO/c1-7(9)5-4-6-8(2,3)10/h7,10H,4-6,9H2,1-3H3 checkY
    Key: LREQLEBVOXIEOM-UHFFFAOYSA-N checkY
  • InChI=1/C8H19NO/c1-7(9)5-4-6-8(2,3)10/h7,10H,4-6,9H2,1-3H3
    Key: LREQLEBVOXIEOM-UHFFFAOYAN
SMILES
  • OC(C)(C)CCCC(N)C
Properties
Chemical formula
 C8H19NO
Molar mass 145.246 g·mol−1
Density 0.895 g/mL
Boiling point 250 °C (482 °F; 523 K)
Pharmacology
ATC code
 C01DX08 (WHO)
Routes of
administration
 Oral, intravenous, intramuscular
Pharmacokinetics:
Excretion
 Renal
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive
GHS labelling:
Pictograms
 GHS05: CorrosiveGHS07: Exclamation mark
Signal word
 Danger
Hazard statements
 H314, H315, H319, H335
Precautionary statements
 P260, P264, P271, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
Flash point 105 °C (221 °F; 378 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Heptaminol is an amino alcohol which is classified as a cardiac stimulant (positive inotropic action). It also increases coronary blood flow along with mild peripheral vasoconstriction. It is sometimes used in the treatment of low blood pressure, particularly orthostatic hypotension as it is a potent positive inotrope (improving cardiac contraction).

Use in doping

Heptaminol is classified by the World Anti-Doping Agency as a doping substance.[1] In 2008, the cyclist Dmitriy Fofonov tested positive for heptaminol at the Tour de France.[2] In June 2010, the swimmer Frédérick Bousquet tested positive.[3] In 2013, the cyclist Sylvain Georges tested positive at the Giro d'Italia.[4] In 2014, baseball player Joel Piniero tested positive[5] as well as St. Louis Cardinals minor league baseball player Yeison Medina.[6]

On March 22, 2019, Cycling South Africa reported that Ricardo Broxham has been sanctioned for an anti-doping rule violation of Articles 2.1 and 2.2 of the UCI Anti-Doping Rules after an in-competition test conducted on 18 August 2018 confirmed the presence of Heptaminol in his sample.

The UCI Anti-Doping Tribunal has imposed a period of ineligibility of 12 months for the violation, applicable as of 22 September 2018 up to and including 22 September 2019 and a disqualification of all results from the 2018 UCI Junior Track Cycling World Championships.[7]

See also

References

  1. ^ "Prohibited in Competition". WADA. Archived from the original on 2019-09-22. Retrieved 2018-10-20.
  2. ^ "Tour rider Fofonov tests positive". BBC. 2008-07-28. Retrieved 2008-07-28.
  3. ^ "France swimmer Bousquet suspended in doping scandal". France24. 2010-10-24. Retrieved 2010-10-23.
  4. ^ "French rider Sylvain Georges tests positive at Giro". ESPN. 2013-05-16. Retrieved 2013-05-16.
  5. ^ "Joel Pineiro suspended 50 games". ESPN. 2014-06-30. Retrieved 2014-06-30.
  6. ^ "Yeison Medina suspended 50 games". ESPN. 2014-09-16. Retrieved 2014-09-16.
  7. ^ "Anti-Doping Rule Violation – In-competition test". Cycling South Africa. Retrieved 2019-03-24.
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