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=CC=CN=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

Molecular Formula C10H14N2O
Molecular Weight 178.231
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
44.65%
NIKETHAMIDE plasma
Homo sapiens
PubMed

PubMed

TitleDatePubMed
Epidemiological analysis of doping offences in the professional tennis circuit.
2010-12-15
Tetra-kis[μ-4-(diethyl-amino)-benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-κN)cobalt(II)].
2010-12-04
Leaf and floral parts feeding by orange tip butterfly larvae depends on larval position but not on glucosinolate profile or nitrogen level.
2010-12
Evolution of diversity in Albugo is driven by high host specificity and multiple speciation events on closely related Brassicaceae.
2010-11
Isolation and structure elucidation of 5'-O-beta-D-glucopyranosyl-dihydroascorbigen from Cardamine diphylla rhizome.
2010-09-03
Hydrotropic solubilization of poorly water-soluble drugs.
2010-09
Diaqua-bis-(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)cobalt(II).
2010-08-18
Differentiating Arabidopsis shoots from leaves by combined YABBY activities.
2010-07
A complex case of simple leaves: indeterminate leaves co-express ARP and KNOX1 genes.
2010-06
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-methyl-benzoato-κO)cobalt(II).
2010-04-21
Tetra-kis(μ-4-methyl-benzoato-κO:O')bis-[(N,N-diethyl-nicotinamide-κN)zinc(II)].
2010-03-31
Novel antagonistic interactions associated with plant polyploidization influence trait selection and habitat preference.
2010-03
Endophytic fungi diversity of aquatic/riparian plants and their antifungal activity in vitro.
2010-02
Cytotype diversity and genome size variation in eastern Asian polyploid Cardamine (Brassicaceae) species.
2010-02
Weeds of change: Cardamine hirsuta as a new model system for studying dissected leaf development.
2010-01
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.
2009-12
Increased D-amino acid oxidase expression in the bilateral hippocampal CA4 of schizophrenic patients: a post-mortem study.
2009-12
Tetra-kis[μ-4-(dimethyl-amino)benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-κN)zinc(II)].
2009-11-14
Tetra-kis[μ-4-(methyl-amino)-benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-N)zinc(II)] dihydrate.
2009-10-10
Application of the isolation with migration model demonstrates the pleistocene origin of geographic differentiation in Cardamine nipponica (Brassicaceae), an endemic Japanese alpine plant.
2009-10
Diaqua-bis-(N,N-diethyl-nicotinamide-κN)bis[4-(dimethyl-amino)-benzoato-κO]cobalt(II).
2009-08-08
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-[4-(dimethyl-amino)benzoato-κO]nickel(II).
2009-07-31
Tetra-kis[μ-4-(diethyl-amino)benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-κN)zinc(II)].
2009-07-18
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.
2009-07-08
Diaqua-bis(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)nickel(II).
2009-06-13
Molecular evolution of phytochromes in Cardamine nipponica (Brassicaceae) suggests the involvement of PHYE in local adaptation.
2009-06
Comment on 'Laparoscopic heminephroureterectomy for duplex kidney anomalies in the pediatric population' by J. Seibold, D. Schilling, U. Nagele, A.G. Anastasiadis, K.D. Sievert, A. Stenzl, S. Corvin. J Pediatr Urol 2008;4:345-7.
2009-06
Diaqua-bis(2-chloro-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)nickel(II).
2009-04-22
Diaqua-bis(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)manganese(II).
2009-04-18
Diaqua-bis(2-chloro-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)manganese(II).
2009-04-10
Diaqua-bis(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)zinc(II).
2009-04-02
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-formyl-benzoato-κO)cobalt(II).
2009-03-11
Comparison of light harvesting and resource allocation strategies between two rhizomatous herbaceous species inhabiting deciduous forests.
2009-03
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-formyl-benzoato-κO)nickel(II).
2009-02-25
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-formyl-benzoato-κO)manganese(II).
2009-02-25
A conserved molecular framework for compound leaf development.
2008-12-19
A cross-species transcriptomics approach to identify genes involved in leaf development.
2008-12-05
A developmental framework for dissected leaf formation in the Arabidopsis relative Cardamine hirsuta.
2008-09
Diaquabis(4-bromo-benzoato-κO)-bis(N,N'-diethyl-nicotinamide-κN)zinc(II).
2008-08-30
Mental state decoding v. mental state reasoning as a mediator between cognitive and social function in psychosis.
2008-07
Consistent geographic structure among multiple nuclear sequences and cpDNA polymorphisms of Cardamine nipponica Franch. et Savat. (Brassicaceae).
2008-07
[Role of 5-HT(2A) receptor in increase in respiratory-related rhythmic discharge activity by nikethamide in neonatal rat transverse medullary slices].
2008-04-25
[GABA A receptor participates in respiratory enhancement induced by nikethamide in neonatal rats].
2008-03
Diaqua-bis(4-chloro-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)manganese(II).
2008-02-29
The correct interpretation and lectotypification of the name Cardamine fallax (Brassicaceae).
2007-09
Interactions among genes in the ErbB-Neuregulin signalling network are associated with increased susceptibility to schizophrenia.
2007-06-28
Hybridization between two polyploid Cardamine (Brassicaceae) species in North-western Spain: discordance between morphological and genetic variation patterns.
2007-06
Butterfly seed predation: effects of landscape characteristics, plant ploidy level and population structure.
2007-05
Impact of foliar herbivory on the development of a root-feeding insect and its parasitoid.
2007-05
Origin of the disjunct tetraploid Cardamine amporitana (Brassicaceae) assessed with nuclear and chloroplast DNA sequence data.
2004-08
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:46:45 GMT 2025
Edited
by admin
on Mon Mar 31 17:46:45 GMT 2025
Record UNII
368IVD6M32
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARDITONIC
Preferred Name English
NIKETHAMIDE
INN   EP  
Official 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 Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
WHO-VATC QR07AB02
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
NCI_THESAURUS C47795
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
WHO-ATC R07AB52
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
Code System Code Type Description
NSC
130820
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
EPA CompTox
DTXSID9046524
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
MESH
D009552
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
DRUG BANK
DB13655
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
CAS
59-26-7
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
SMS_ID
100000091927
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
NCI_THESAURUS
C76625
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
WIKIPEDIA
NIKETHAMIDE
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
PUBCHEM
5497
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-418-5
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
MERCK INDEX
m7897
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY Merck Index
RXCUI
7424
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY RxNorm
EVMPD
SUB09286MIG
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
INN
403
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
ChEMBL
CHEMBL2104607
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
DRUG CENTRAL
3383
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
FDA UNII
368IVD6M32
Created by admin on Mon Mar 31 17:46:45 GMT 2025 , Edited by admin on Mon Mar 31 17:46:45 GMT 2025
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY