Nikethamide
{{Short description|Chemical compound}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 447430580
| IUPAC_name = N,N-Diethyl-3-pyridinecarboxamide
| image = Nikethamide.svg
| image2 = Nikethamide molecule ball.png
| width = 150
| tradename = Coramine
| Drugs.com = {{drugs.com|international|nikethamide}}
| pregnancy_category =
| legal_status =
| routes_of_administration =
| bioavailability =
| metabolism =
| elimination_half-life = 0.5 h
| excretion =
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 59-26-7
| ATC_prefix = R07
| ATC_suffix = AB02
| PubChem = 5497
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5296
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 368IVD6M32
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07408
| ChEMBL = 2104607
| ChEBI = 134814
| DrugBank = DB13655
| synonyms = Nicotinic acid diethylamide
| C = 10
| H = 14
| N = 2
| O = 1
| smiles = O=C(N(CC)CC)c1cccnc1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H14N2O/c1-3-12(4-2)10(13)9-6-5-7-11-8-9/h5-8H,3-4H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NCYVXEGFNDZQCU-UHFFFAOYSA-N
}}
Nikethamide is a stimulant which mainly affects the respiratory cycle. Widely known by its former trade name of Coramine, it was used in the mid-twentieth century as a medical countermeasure against tranquilizer overdoses, before the advent of endotracheal intubation and positive-pressure lung expansion. It is no longer commonly considered to be of value for such purposes.{{Citation needed|date=March 2025}}
In alternate terminology, it is known as nicotinic acid diethylamide, which meaningfully emphasizes its laboratory origins, and of which its common name is derived as a blend.{{Citation needed|date=March 2025}}
Uses
It is useful for mountain climbers to increase endurance at high altitudes.[http://www.toxcenter.de/stoff-infos/n/nikethamid.pdf Nikethamid] {{Webarchive|url=https://web.archive.org/web/20110722003658/http://www.toxcenter.de/stoff-infos/n/nikethamid.pdf|date=2011-07-22}}, III-3.3, Toxcenter
= Available forms =
It is available as a short-acting over-the-counter drug in several South American and European countries, combined with glucose in form of lozenges.{{Citation needed|date=March 2025}}
Contraindications
Contraindications include hypertension, cardiovascular disease, and epilepsy.
Society and culture
File:Box, metal (AM 2001.25.1277-1).jpg, New Zealand)]] Coramine was used by suspected serial killer John Bodkin Adams when treating patient Gertrude Hullett, whom he was suspected of murdering.{{cite book | last = Cullen | first = Pamela V. | name-list-style = vanc | title = A Stranger in Blood: The Case Files on Dr John Bodkin Adams | location = London | publisher = Elliott & Thompson | date = 2006 | isbn = 1-904027-19-9 }} However, the toxicity of nikethamide is quite low ({{LD50}} rabbits 650 mg/kg oral, LD50 rats 240 mg/kg subcutaneous).{{Citation needed|date=March 2025}}
Theodor Morell, Adolf Hitler's personal physician, would inject the German ruler with Coramine when Hitler was unduly sedated with barbiturates. In addition, Morell would use Coramine as part of an all-purpose "tonic" for Hitler.{{cite journal | vauthors = Doyle D | title = Adolf Hitler's medical care | journal = The Journal of the Royal College of Physicians of Edinburgh | volume = 35 | issue = 1 | pages = 75–82 | date = February 2005 | pmid = 15825245 | url = http://www.rcpe.ac.uk/journal/issue/journal_35_1/Hitler's_medical_care.pdf | oclc = 49953788 }}
= Use in sports =
In some sports, nikethamide is listed by the World Anti-Doping Agency as a banned substance. Jaime Huélamo was stripped of his bronze medal at the 1972 Olympic individual cycling road race after testing positive for Coramine.{{cite web | title = Olympic doping's list of shame | url = https://www.news24.com/xArchive/Olympics2004/InsideTrack/Olympic-dopings-list-of-shame-20040824 | date = 24 August 2004 | work = News24Wire · }} Croatian tennis player Marin Čilić was suspended from competition for nine months after he tested positive for nikethamide in April 2013.{{cite news|url=https://www.bbc.co.uk/sport/0/tennis/24116444|title=Marin Cilic: Croatian banned for nine months|work=BBC News|date=16 September 2013|access-date=16 September 2013}} This ban was later reduced to four months after Cilic appealed and claimed he had unintentionally ingested it in a glucose tablet bought at a pharmacy.{{cite news|url=http://www.tennis.com/pro-game/2013/10/cilic-cleared-play-again-after-suspension-reduced/49565/#.UmqAnfmsiSo|title=Cilic cleared to play again after suspension reduced|work=Tennis|date=25 October 2013|access-date=25 October 2013}} Polish kart driver Igor Walilko was given a two-year ban, later reduced to eighteen months, from competition in 2010 due to testing positive for nikethamide after a win in Germany in July, 2010.{{cite web |url=http://www.fia.com/sites/default/files/basicpage/file/10-10-11c-WALILKO-Decision-CAS.pdf |work = FIA Anti-Doping Disciplinary Committee | first = Igor | last = Walilko | name-list-style = vanc | title = Decision of the Court of Arbitration for Sport |date=22 September 2011 |access-date=23 July 2016}}
In July 2021, Swiss athlete and doctor Kariem Hussein was positively tested for nikethamide, which he regularly uses during training. He missed the 2020 Summer Olympics in Tokyo, and was banned from competitions for nine months.{{Cite web|url=https://www.20min.ch/story/diese-lutschtablette-wurde-kariem-hussein-zum-verhaengnis-235882779074|title=Diese Lutschtablette wurde Kariem Hussein zum Verhängnis|date=2021-07-23|website=20 Minuten|language=de}}
See also
References
{{Reflist}}
External links
- {{DiseasesDB|33087}}
{{Respiratory stimulants}}