Nikethamide

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.

Nikethamide
Clinical data
Other namesNicotinic acid diethylamide
AHFS/Drugs.comInternational Drug Names
ATC code
Pharmacokinetic data
Elimination half-life0.5 h
Identifiers
IUPAC name
  • N,N-Diethyl-3-pyridinecarboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.380
Chemical and physical data
FormulaC10H14N2O
Molar mass178.231 g·mol−1
3D model (JSmol)
SMILES
  • O=C(N(CC)CC)c1cccnc1
InChI
  • InChI=1S/C10H14N2O/c1-3-12(4-2)10(13)9-6-5-7-11-8-9/h5-8H,3-4H2,1-2H3 Y
  • Key:NCYVXEGFNDZQCU-UHFFFAOYSA-N Y
  (verify)

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.

Former and current medical use
Coramine injection kit from the Second World War (Auckland War Memorial Museum, New Zealand)

Coramine was used by suspected serial killer John Bodkin Adams when treating patient Gertrude Hullett, whom he was suspected of murdering.[1] However, the toxicity of nikethamide is quite low (LD50 rabbits 650 mg/kg oral, LD50 rats 240 mg/kg subcutaneous).

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.[2]

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. It is especially useful for mountain climbers to increase endurance at high altitudes. Contraindications include hypertension, cardiovascular pathologies and epilepsy.[3]

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.[4] Croatian tennis player Marin Čilić was suspended from competition for nine months after he tested positive for nikethamide in April 2013.[5] 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.[6] 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.[7]

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.[8]

See also

References
  1. Cullen PV (2006). A Stranger in Blood: The Case Files on Dr John Bodkin Adams. London: Elliott & Thompson. ISBN 1-904027-19-9.
  2. Doyle D (February 2005). "Adolf Hitler's medical care" (PDF). The Journal of the Royal College of Physicians of Edinburgh. 35 (1): 75–82. OCLC 49953788. PMID 15825245.
  3. Nikethamid Archived 2011-07-22 at the Wayback Machine, III-3.3, Toxcenter
  4. "Olympic doping's list of shame". News24Wire ·. 24 August 2004.
  5. "Marin Cilic: Croatian banned for nine months". BBC News. 16 September 2013. Retrieved 16 September 2013.
  6. "Cilic cleared to play again after suspension reduced". Tennis. 25 October 2013. Retrieved 25 October 2013.
  7. Walilko I (22 September 2011). "Decision of the Court of Arbitration for Sport" (PDF). FIA Anti-Doping Disciplinary Committee. Retrieved 23 July 2016.
  8. "Diese Lutschtablette wurde Kariem Hussein zum Verhängnis". 20 Minuten (in German). 2021-07-23.
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