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{{chembox
{{Chembox
| Verifiedfields = changed
| UNII_Ref = {{fdacite|correct|FDA}}
| Watchedfields = changed
| UNII = 3DQS188SY5
| verifiedrevid = 443432462
| verifiedrevid = 447116909
| ImageFile = Heptaminol.svg
| ImageFile = Heptaminol.svg
| ImageSize = 220px
| ImageSize = 200px
| IUPACName = 6-amino-2-methylheptan-2-ol
| IUPACName = (''RS'')-6-Amino-2-methylheptan-2-ol
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| Abbreviations =
| CASNo = 372-66-7
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3464
| ChemSpiderID = 3464
| ChEBI = 94362
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2111076
| DrugBank = DB13574
| EC_number = 206-758-0
| EINECS =
| PubChem = 3590
| RTECS =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3DQS188SY5
| MeSHName = Heptaminol
| InChI = 1/C8H19NO/c1-7(9)5-4-6-8(2,3)10/h7,10H,4-6,9H2,1-3H3
| InChI = 1/C8H19NO/c1-7(9)5-4-6-8(2,3)10/h7,10H,4-6,9H2,1-3H3
| InChIKey = LREQLEBVOXIEOM-UHFFFAOYAN
| InChIKey = LREQLEBVOXIEOM-UHFFFAOYAN
Line 17: Line 30:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LREQLEBVOXIEOM-UHFFFAOYSA-N
| StdInChIKey = LREQLEBVOXIEOM-UHFFFAOYSA-N
| SMILES = OC(C)(C)CCCC(N)C
| CASNo = 372-66-7
}}
| EINECS =
|Section2={{Chembox Properties
| PubChem = 3590
| C=8 | H=19 | N=1 | O=1
| SMILES = OC(C)(C)CCCC(N)C
| InChI =
| Appearance =
| RTECS =
| Density = 0.895 g/mL
| MeltingPt =
| MeSHName =Heptaminol
| BoilingPtC = 250
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI =
| Solubility =
}}
| KEGG_Ref = {{keggcite|correct|kegg}}
|Section6={{Chembox Pharmacology
| KEGG =
| ATCCode_prefix = C01
| ATCCode_prefix = C01
| ATCCode_suffix = DX08
| ATCCode_suffix = DX08
| AdminRoutes = Oral, [[intravenous therapy|intravenous]], [[intramuscular injection|intramuscular]]
| ATC_Supplemental =
| Bioavail =
}}
| Metabolism =
| Section2 = {{Chembox Properties
| HalfLife =
|C=8|H=19|N=1|O=1
| ProteinBound =
| MolarMass = 145.243 g/mol
| Excretion = [[Kidney|Renal]]
| Appearance =
| Density =
| Legal_status =
| MeltingPt =
| Legal_US =
| BoilingPt =
| Legal_UK =
| Legal_AU =
}}
| Legal_CA =
| Section3 = {{Chembox Pharmacology
| Pregnancy_category =
| AdminRoutes = Oral, [[intravenous therapy|intravenous]], [[intramuscular injection|intramuscular]]
| Bioavail =
| Pregnancy_AU =
}}
| Metabolism =
|Section7={{Chembox Hazards
| HalfLife =
| MainHazards = Corrosive
| ProteinBound =
| FlashPtC = 105
| Excretion = [[Kidney|Renal]]
| GHSPictograms = {{GHS05}}{{GHS07}}
| Legal_status =
| GHSSignalWord = Danger
| Legal_US =
| HPhrases = {{H-phrases|314|315|319|335}}
| Legal_UK =
| PPhrases = {{P-phrases|260|261|264|271|280|301+330+331|302+352|303+361+353|304+340|305+351+338|310|312|321|332+313|337+313|362|363|403+233|405|501}}
| Legal_AU =
| Legal_CA =
| AutoignitionPt =
}}
| PregCat =
| PregCat_AU =
| PregCat_US =
}}
| Section4 = {{Chembox Hazards
| Solubility =
| MainHazards =
| FlashPt =
| Autoignition =
}}
}}
}}


'''Heptaminol''' is an [[amino alcohol]] which is classified as a [[vasodilator]] ({{ATC|C01|DX08}}). It is sometimes used in the treatment of [[hypotension|low blood pressure]], particularly [[orthostatic hypotension]].<ref>{{fr icon}} {{cite web | url = http://www.biam2.org/www/Sub1530.html | title = Heptaminol Chlorhydrate | accessdate = 2007-02-27 | date = March 3, 2000 | publisher = BIAM}}</ref>
'''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).{{medcn|date=October 2018}}


==Use in doping==
It is classified as a [[Doping (sport)|doping]] substance, in 2008 the cyclist [[Dmitriy Fofonov]] was tested positive at the [[Tour de France]]<ref>{{cite web
Heptaminol is classified by the [[World Anti-Doping Agency]] as a [[Doping (sport)|doping]] substance.<ref>{{Cite web | url = https://www.wada-ama.org/en/content/what-is-prohibited/prohibited-in-competition | title = Prohibited in Competition | publisher = WADA | access-date = 2018-10-20 | archive-date = 2019-09-22 | archive-url = https://web.archive.org/web/20190922090208/https://www.wada-ama.org/en/content/what-is-prohibited/prohibited-in-competition | url-status = dead }}</ref> In 2008, the cyclist [[Dmitriy Fofonov]] tested positive for heptaminol at the [[Tour de France]].<ref>{{cite web|title = Tour rider Fofonov tests positive|publisher = BBC| date = 2008-07-28| url = http://news.bbc.co.uk/sport2/hi/other_sports/cycling/7527891.stm|access-date = 2008-07-28}}</ref> In June 2010, the swimmer [[Frédérick Bousquet]] tested positive.<ref>{{cite web|title = France swimmer Bousquet suspended in doping scandal|publisher = France24| date = 2010-10-24| url = http://www.france24.com/en/20101020-france-swimmer-bousquet-serving-doping-suspension-scandal-sport| access-date = 2010-10-23}}</ref> In 2013, the cyclist [[Sylvain Georges]] tested positive at the [[Giro d'Italia]].<ref>{{cite web| title = French rider Sylvain Georges tests positive at Giro| publisher = ESPN| date = 2013-05-16| url = http://www.espn.com/endurance/story/_/id/9277088/french-rider-sylvain-georges-tests-positive-giro| access-date = 2013-05-16}}</ref> In 2014, baseball player [[Joel Piniero]] tested positive<ref>{{cite web| title = Joel Pineiro suspended 50 games| publisher = ESPN| date = 2014-06-30| url = https://www.espn.com/mlb/story/_/id/11158895/joel-pineiro-former-mlb-pitcher-suspended-50-games-testing-positive-banned-stimulant| access-date = 2014-06-30}}</ref> as well as [[St. Louis Cardinals]] [[minor league]] baseball player Yeison Medina.<ref>{{cite web| title = Yeison Medina suspended 50 games| publisher = ESPN| date = 2014-09-16| url = https://www.espn.com/minor-league-baseball/story/_/id/11539694/st-louis-cardinals-minor-leaguer-yeison-medina-suspended-50-games| access-date = 2014-09-16}}</ref>
| title = Tour rider Fofonov tests positive

| publisher = BBC
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.
| date = 2008-07-28

| url = http://news.bbc.co.uk/sport2/hi/other_sports/cycling/7527891.stm
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.<ref>{{Cite web|url=https://www.cyclingsa.com/news-and-press/2019/3/22/anti-doping-rule-violation-in-competition-test|title=Anti-Doping Rule Violation – In-competition test|website=Cycling South Africa|language=en-ZA|access-date=2019-03-24}}</ref>
| accessdate = 2008-07-28}}
</ref>. In 2010 June the swimmer [[Frédérick Bousquet]] was tested positive for the substance, allegely for buying a medicine from the pharmacy<ref>{{cite web
| title = France swimmer Bousquet suspended in doping scandal
| publisher = France24
| date = 2010-10-24
| url = http://www.france24.com/en/20101020-france-swimmer-bousquet-serving-doping-suspension-scandal-sport
| accessdate = 2010-10-23}}
</ref>.


== See also ==
== See also ==
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{{Stimulants}}
{{Stimulants}}
{{Amino alcohols}}
{{Vasodilators used in cardiac diseases}}
{{Vasodilators used in cardiac diseases}}
{{Monoamine releasing agents}}
{{Adrenergics}}


[[Category:Vasodilators]]
[[Category:Vasodilators]]
[[Category:Amines]]
[[Category:Amines]]
[[Category:Alcohols]]
[[Category:Tertiary alcohols]]

[[de:Heptaminol]]
[[fr:Heptaminol]]
[[hu:Heptaminol]]
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