U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H14N2O
Molecular Weight 178.231
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIKETHAMIDE

SMILES

CCN(CC)C(=O)C1=CN=CC=C1

InChI

InChIKey=NCYVXEGFNDZQCU-UHFFFAOYSA-N
InChI=1S/C10H14N2O/c1-3-12(4-2)10(13)9-6-5-7-11-8-9/h5-8H,3-4H2,1-2H3

HIDE SMILES / InChI
Nikethamide is a respiratory and circulatory stimulant with some central nervous system activity. 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. Nikethamide is available as a short-acting over-the-counter drug in several South American and European countries, combined with glucose in form of lozenges. Nikethamide is especially useful for mountain climbers to increase endurance at high altitudes. Contraindications include hypertension, cardiovascular pathologies, and epilepsy. In some sports, nikethamide is listed by the World Anti-Doping Agency as a banned substance. Croatian tennis player Marin Čilić was suspended from competition for nine months after he tested positive for nikethamide in April 2013

Originator

Sources: Zeitschrift fuer die Gesamte Experimentelle Medizin 52, 197-213. From: Chem. Zentr. 1926, II, 2456.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Coramine

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Origin of the disjunct tetraploid Cardamine amporitana (Brassicaceae) assessed with nuclear and chloroplast DNA sequence data.
2004 Aug
The role of serendipity in drug discovery.
2006
The difference between simple and complex leaves.
2006 Aug
The genetic basis for differences in leaf form between Arabidopsis thaliana and its wild relative Cardamine hirsuta.
2006 Aug
Antioxidant activity of wild plants collected in Valsesia, an alpine region of Northern Italy.
2006 Jul
Simultaneous determination of nikethamide and lidocaine in human blood and cerebrospinal fluid by high performance liquid chromatography.
2007 Apr 11
Hydrotropic polymeric micelles for enhanced paclitaxel solubility: in vitro and in vivo characterization.
2007 Jan
Hybridization between two polyploid Cardamine (Brassicaceae) species in North-western Spain: discordance between morphological and genetic variation patterns.
2007 Jun
Interactions among genes in the ErbB-Neuregulin signalling network are associated with increased susceptibility to schizophrenia.
2007 Jun 28
Butterfly seed predation: effects of landscape characteristics, plant ploidy level and population structure.
2007 May
Impact of foliar herbivory on the development of a root-feeding insect and its parasitoid.
2007 May
The correct interpretation and lectotypification of the name Cardamine fallax (Brassicaceae).
2007 Sep
[Role of 5-HT(2A) receptor in increase in respiratory-related rhythmic discharge activity by nikethamide in neonatal rat transverse medullary slices].
2008 Apr 25
Diaquabis(4-bromo-benzoato-κO)-bis(N,N'-diethyl-nicotinamide-κN)zinc(II).
2008 Aug 30
A conserved molecular framework for compound leaf development.
2008 Dec 19
A cross-species transcriptomics approach to identify genes involved in leaf development.
2008 Dec 5
Diaqua-bis(4-chloro-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)manganese(II).
2008 Feb 29
Mental state decoding v. mental state reasoning as a mediator between cognitive and social function in psychosis.
2008 Jul
Consistent geographic structure among multiple nuclear sequences and cpDNA polymorphisms of Cardamine nipponica Franch. et Savat. (Brassicaceae).
2008 Jul
[GABA A receptor participates in respiratory enhancement induced by nikethamide in neonatal rats].
2008 Mar
Diaqua-bis(2-chloro-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)manganese(II).
2009 Apr 10
Diaqua-bis(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)manganese(II).
2009 Apr 18
Diaqua-bis(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)zinc(II).
2009 Apr 2
Diaqua-bis(2-chloro-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)nickel(II).
2009 Apr 22
Diaqua-bis-(N,N-diethyl-nicotinamide-κN)bis[4-(dimethyl-amino)-benzoato-κO]cobalt(II).
2009 Aug 8
Molecular cloning and characterization of a KCS gene from Cardamine graeca and its heterologous expression in Brassica oilseeds to engineer high nervonic acid oils for potential medical and industrial use.
2009 Dec
Increased D-amino acid oxidase expression in the bilateral hippocampal CA4 of schizophrenic patients: a post-mortem study.
2009 Dec
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-formyl-benzoato-κO)nickel(II).
2009 Feb 25
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-formyl-benzoato-κO)manganese(II).
2009 Feb 25
Tetra-kis[μ-4-(diethyl-amino)benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-κN)zinc(II)].
2009 Jul 18
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-[4-(dimethyl-amino)benzoato-κO]nickel(II).
2009 Jul 31
Evidence for the association of the DAOA (G72) gene with schizophrenia and bipolar disorder but not for the association of the DAO gene with schizophrenia.
2009 Jul 8
Molecular evolution of phytochromes in Cardamine nipponica (Brassicaceae) suggests the involvement of PHYE in local adaptation.
2009 Jun
Diaqua-bis(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)nickel(II).
2009 Jun 13
Comparison of light harvesting and resource allocation strategies between two rhizomatous herbaceous species inhabiting deciduous forests.
2009 Mar
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-formyl-benzoato-κO)cobalt(II).
2009 Mar 11
Tetra-kis[μ-4-(dimethyl-amino)benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-κN)zinc(II)].
2009 Nov 14
Tetra-kis[μ-4-(methyl-amino)-benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-N)zinc(II)] dihydrate.
2009 Oct 10
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-methyl-benzoato-κO)cobalt(II).
2010 Apr 21
Diaqua-bis-(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)cobalt(II).
2010 Aug 18
Leaf and floral parts feeding by orange tip butterfly larvae depends on larval position but not on glucosinolate profile or nitrogen level.
2010 Dec
Epidemiological analysis of doping offences in the professional tennis circuit.
2010 Dec 15
Tetra-kis[μ-4-(diethyl-amino)-benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-κN)cobalt(II)].
2010 Dec 4
Cytotype diversity and genome size variation in eastern Asian polyploid Cardamine (Brassicaceae) species.
2010 Feb
Weeds of change: Cardamine hirsuta as a new model system for studying dissected leaf development.
2010 Jan
Differentiating Arabidopsis shoots from leaves by combined YABBY activities.
2010 Jul
Novel antagonistic interactions associated with plant polyploidization influence trait selection and habitat preference.
2010 Mar
Tetra-kis(μ-4-methyl-benzoato-κO:O')bis-[(N,N-diethyl-nicotinamide-κN)zinc(II)].
2010 Mar 31
Evolution of diversity in Albugo is driven by high host specificity and multiple speciation events on closely related Brassicaceae.
2010 Nov
Isolation and structure elucidation of 5'-O-beta-D-glucopyranosyl-dihydroascorbigen from Cardamine diphylla rhizome.
2010 Sep 3
Patents

Patents

Sample Use Guides

In Vivo Use Guide
administered to adults in a dose of 1-2 ml 1-3 times a day, children under the skin - 0.1-0.75 ml
Route of Administration: Other
In Vitro Use Guide
Unknown
Name Type Language
NIKETHAMIDE
INN   EP  
Official Name English
CARDITONIC
Brand Name English
Nikethamide [WHO-DD]
Common Name English
NIKETHAMIDE [MI]
Common Name English
NSC-130820
Code English
NIKETHYL
Brand Name English
NIKETHAMIDE [EP MONOGRAPH]
Common Name English
nikethamide [INN]
Common Name English
CORAMINE
Brand Name English
N,N-DIETHYLNICOTINAMIDE
Systematic Name English
NIKETHAMIDE [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC R07AB02
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
WHO-VATC QR07AB02
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
NCI_THESAURUS C47795
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
WHO-ATC R07AB52
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
Code System Code Type Description
NSC
130820
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID9046524
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
MESH
D009552
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
DRUG BANK
DB13655
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
CAS
59-26-7
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
SMS_ID
100000091927
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
NCI_THESAURUS
C76625
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
WIKIPEDIA
NIKETHAMIDE
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
PUBCHEM
5497
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-418-5
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
MERCK INDEX
m7897
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY Merck Index
RXCUI
7424
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY RxNorm
EVMPD
SUB09286MIG
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
INN
403
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104607
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
DRUG CENTRAL
3383
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
FDA UNII
368IVD6M32
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY