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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H19N
Molecular Weight 225.3288
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEFETAMINE

SMILES

CN(C)[C@H](CC1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=YEJZJVJJPVZXGX-MRXNPFEDSA-N
InChI=1S/C16H19N/c1-17(2)16(15-11-7-4-8-12-15)13-14-9-5-3-6-10-14/h3-12,16H,13H2,1-2H3/t16-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16991666 | https://www.ncbi.nlm.nih.gov/pubmed/26276083 | https://www.ncbi.nlm.nih.gov/pubmed/1417455

Lefetamine (L-SPA; L-1,2-diphenyl-l-dimethylaminoethane hydrochloride) is a synthetic compound with analgesic and anti-inflammatory action, introduced in clinical practice in Italy and Japan as ‘Santenol’. Santenol is available for oral (50 mg tablets1 and intramuscular (60 mg vials containing also lidocainel use. Animal studies have shown an analgesic effect and changes in EEG activity and O2 consumption of the nervous tissue. Lefetamine may be an opioid partial agonist. Lefetamine was first marketed in the 1940s as an opioid analgesic. Since withdrawal symptoms were observed during treatment, it became a controlled substance.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Treatment of polydrug-using opiate dependents during withdrawal: towards a standardisation of treatment.
2006 Nov 15
Toxicokinetics of lefetamine and derived diphenylethylamine designer drugs-Contribution of human cytochrome P450 isozymes to their main phase I metabolic steps.
2015 Nov 4
Patents

Patents

Sample Use Guides

In clinical trial patients were assigned to lefetamine treatment programme. After stabilization on admission with a sufficient lefetamine dosage (mean 450 mg/day) five of them underwent a progressive lefetamine withdrawal with increasing sedative-antimanic therapy (neuroleptics such as levopromazine, chlorpromazine or sodium valproatel.
Route of Administration: Oral
Incubation mixtures (final volume: 50 mkL) consisted of 90 mM phosphate buffer (pH 7.4), 5 mM Mg2+, 5 mM isocitrate, 1.2 mM NADP+, 0.5 U/mL isocitrate dehydrogenase, 200 U/mL superoxide dismutase, liver enzymes and the LEFETAMINE (up to 1000mkM), diluted in the phosphate buffer. Reactions were started by addition of the ice-cold microsomes and stopped with 50 mkL of an ice-cold mixture of acetonitrile, containing the IS (diphenhydramine, 10 mkM). The solutions were centrifuged for 2 min at 14,000 x g, 50 mkL of the supernatant was transferred to an autosampler vial and injected onto the LC–MSn system.
Name Type Language
LEFETAMINE
INN   MI   WHO-DD  
INN  
Official Name English
Lefetamine [WHO-DD]
Common Name English
(-)-N,N-DIMETHYL-1,2-DIPHENYLETHYLAMINE
Systematic Name English
lefetamine [INN]
Common Name English
LEFETAMINE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Fri Dec 15 16:39:20 GMT 2023 , Edited by admin on Fri Dec 15 16:39:20 GMT 2023
DEA NO. 1635
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Code System Code Type Description
INN
3457
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EPA CompTox
DTXSID7046833
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MERCK INDEX
m1201
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PRIMARY Merck Index
WIKIPEDIA
LEFETAMINE
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SMS_ID
100000082585
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NCI_THESAURUS
C81381
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CAS
7262-75-1
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DRUG CENTRAL
3316
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ChEMBL
CHEMBL2106355
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FDA UNII
4J9726V5Y9
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EVMPD
SUB08423MIG
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PUBCHEM
443970
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MESH
C011896
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