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

Details

Stereochemistry RACEMIC
Molecular Formula C7H15NO3
Molecular Weight 161.1989
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARNITINE

SMILES

C[N+](C)(C)CC(O)CC([O-])=O

InChI

InChIKey=PHIQHXFUZVPYII-UHFFFAOYSA-N
InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C7H15NO3
Molecular Weight 161.1989
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

L-carnitine (L-beta-hydroxy-gamma-N,N,N-trimethylaminobutyric acid) is conditionally necessary for mitochondrial transport and metabolism of long-chain fatty acids, and thus for myocardial energetic metabolism. D-carnitine is not biologically active and might interfere with proper utilization of the L isomer, and so there are claims that the racemic mixture (DL-carnitine) should be avoided. The pharmacological effects of carnitine are stereospecific: L-carnitine was effective in various animal and clinical studies, while D- and DL-carnitine was found to be ineffective or even toxic to some cells and tissues, such as muscle cells and the myocardium. DL-carnitine caused symptoms of myasthenia and cardiac arrhythmias, which disappeared after L-carnitine administration.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Carnitine protection against adriamycin-induced cardiomyopathy in rats.
1986 Feb 10
Carnitine deficiency associated with long-term pivampicillin treatment: the effect of a replacement therapy regime.
1992 Nov
Effect of L-carnitine supplementation on acute valproate intoxication.
1996 Jul
Attenuation of levodopa-induced dyskinesia by normalizing dopamine D3 receptor function.
2003 Jun
Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3.
2004 May
Lethal cardiomyopathy in epidermolysis bullosa associated with amitriptyline.
2005 Aug
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Involvement of recognition and interaction of carnitine transporter in the decrease of L-carnitine concentration induced by pivalic acid and valproic acid.
2006 Aug
Mechanism of the inhibitory effect of zwitterionic drugs (levofloxacin and grepafloxacin) on carnitine transporter (OCTN2) in Caco-2 cells.
2006 Nov
L-carnitine mediates protection against DNA damage in lymphocytes of aged rats.
2009 Apr
Carnitine deficiency: a possible risk factor in paracetamol hepatotoxicity.
2009 Feb
Inactivation by omeprazole of the carnitine transporter (OCTN2) reconstituted in liposomes.
2009 May 15
Vincristine-induced peripheral neuropathy in a neonate with congenital acute lymphoblastic leukemia.
2010 Apr
Inhibition of gene expression of heart fatty acid binding protein and organic cation/carnitine transporter in doxorubicin cardiomyopathic rat model.
2010 Aug 25
Valproate-induced hyperammonemic encephalopathy, rapidly improved by i.v. carnitine and glucose/thiamine.
2010 Jun
Selective regulation of cardiac organic cation transporter novel type 2 (OCTN2) in dilated cardiomyopathy.
2011 Jun
The protection role of heat shock protein 70 (HSP-70) in the testes of cadmium-exposed rats.
2012
Inhibition of mitochondrial carnitine/acylcarnitine transporter by H(2)O(2): molecular mechanism and possible implication in pathophysiology.
2013 Apr 25
Patents

Sample Use Guides

in rat: supplemented with dl-carnitine (DLC) (1.2 mmol . kg-1. d-1)
Route of Administration: Oral
Using rat phrenic nerve diaphragm preparations indirectly and directly stimulated with high rate pulses, D-carnitine (30 and 60 micro M), L-carnitine (60 micro M) and DL-carnitine (60 micro M) were shown to induce tetanic fade (D-carnitine = 19.7 +/- 3.1%, N = 6; L-carnitine = 16.6 +/- 2.4%, N = 6; DL-carnitine = 14.9 +/- 2.1%, N = 6) without any reduction of maximal tetanic tension. It was shown, that tetanic fade induced by L- and DL-carnitine was antagonized by choline (60 micro M).
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:44:22 UTC 2023
Edited
by admin
on Wed Jul 05 22:44:22 UTC 2023
Record UNII
S7UI8SM58A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARNITINE
INCI   INN   MART.   VANDF   WHO-DD  
INN   INCI  
Official Name English
CARNITINE, DL-
Common Name English
CARNITINE [MART.]
Common Name English
CARNITINE DL-FORM [MI]
Common Name English
DL-CARNITINE
Common Name English
CARNITINE [INCI]
Common Name English
CARNITINE [VANDF]
Common Name English
Carnitine [WHO-DD]
Common Name English
carnitine [INN]
Common Name English
(3-CARBOXY-2-HYDROXYPROPYL)TRIMETHYLAMMONIUM HYDROXIDE INNER SALT
Common Name English
NSC-757390
Code English
Classification Tree Code System Code
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CFR 21 CFR 862.1055
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Code System Code Type Description
SMS_ID
100000090457
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
PRIMARY
CHEBI
39547
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
PRIMARY
INN
4083
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
PRIMARY
RXCUI
2106
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C82599
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
PRIMARY
EVMPD
SUB06134MIG
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
PRIMARY
FDA UNII
S7UI8SM58A
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
PRIMARY
PUBCHEM
288
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
PRIMARY
CAS
461-06-3
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
SUPERSEDED
CHEBI
17126
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
PRIMARY
CHEBI
16347
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL172513
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
PRIMARY
MESH
D002331
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
PRIMARY
WIKIPEDIA
CARNITINE
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
PRIMARY
EPA CompTox
DTXSID3022744
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
CONCEPT Dietary Supplement
CHEBI
3424
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
PRIMARY
MERCK INDEX
M3119
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
PRIMARY Merck Index
NSC
757390
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
PRIMARY
CAS
406-76-8
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
PRIMARY
DAILYMED
S7UI8SM58A
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Km
ENANTIOMER -> RACEMATE
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY