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 ( + / - )

Description

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.

CNS Activity

Approval Year

2009
334
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

Patents

05385829
14
06566552
3
JP2002544218A
14
JP2007308379A
3
JP2008520236A
3
JP2010142237A
3
JP2010163465A
3
JP2010227113A
6
JP2010254717A
3
JP2011088912A
3
JPH00279967A
3
JPH00324010A
3
JPH00361499A
3
JPH00523190A
3
JPH01213259A
3
JPH0269188A
3
JPH0427395A
3
JPH05103596A
3
JPH05194206A
3
JPH05221940A
3
JPH07119A
3
JPH0767674A
3
JPH0892181A
3
JPH09176005A
3
JPS57126420A
3
JPS59192095A
3
JPS61242585A
3
JPS62275689A
3

Sample Use Guides

In Vivo Use Guide
in rat: supplemented with dl-carnitine (DLC) (1.2 mmol . kg-1. d-1)
Route of Administration: Oral
In Vitro Use Guide
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
LOINC 53096-4
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 2047-9
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 22695-1
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 2048-7
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 88008-8
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 55200-0
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 17867-3
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 14285-1
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 34259-2
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 2042-0
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 24453-3
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 53235-8
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 44710-2
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 38481-8
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 14288-5
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 88007-0
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 54442-9
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
FDA ORPHAN DRUG 780220
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 38480-0
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 53071-7
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 53233-3
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 53234-1
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 48430-3
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 14287-7
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 43576-8
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 16556-3
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 53112-9
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 45192-2
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 2045-3
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 53238-2
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 24448-3
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
CFR 21 CFR 862.1055
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 2046-1
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 88024-5
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 22704-1
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 18363-2
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 88011-2
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 53072-5
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 30193-7
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 16555-5
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 2043-8
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 53054-3
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 43186-6
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 88025-2
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 53171-5
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 53236-6
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 13718-2
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 59206-3
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
FDA ORPHAN DRUG 599517
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 24451-7
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 34257-6
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 88006-2
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 40869-0
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 2044-6
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 24452-5
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 14286-9
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 16553-0
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 10561-9
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 32281-8
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 26788-0
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 32613-2
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 34258-4
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 53095-6
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 53053-5
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 10877-9
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 17866-5
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 88014-6
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
LOINC 13719-0
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 26757-5
Created by admin on Wed Jul 05 22:44:22 UTC 2023 , Edited by admin on Wed Jul 05 22:44:22 UTC 2023
LOINC 53162-4
Created by admin on Wed Jul 05 22:44:23 UTC 2023 , Edited by admin on Wed Jul 05 22:44:23 UTC 2023
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
Structure of LEVOCARNITINE
ENANTIOMER -> RACEMATE
Structure of CARNITINE OROTATE
SALT/SOLVATE -> PARENT
Structure of CARNITINE CHLORIDE
SALT/SOLVATE -> PARENT
OCTN-2
TRANSPORTER -> SUBSTRATE
Km
Structure of CARNITINE, (+)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of (2-OXOPROPYL)TRIMETHYLAMMONIUM
METABOLITE -> PARENT
Related Record Type Details
Structure of CARNITINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966