LEFETAMINE

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 Search

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

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2571492
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2571492	Partial Agonist 290

Conditions

Condition	Modality	Targets	Highest Phase	Product
Drug addiction 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2571492	Primary		Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Treatment of polydrug-using opiate dependents during withdrawal: towards a standardisation of treatment.	2006 Nov 15	17107609
Toxicokinetics of lefetamine and derived diphenylethylamine designer drugs-Contribution of human cytochrome P450 isozymes to their main phase I metabolic steps.	2015 Nov 4	26276083

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

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