Page last updated: 2024-09-26

desmethylselegiline

Description

desmethylselegiline: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID200718
CHEMBL ID1276
SCHEMBL ID4543249
MeSH IDM0068954
PubMed CID185859
CHEMBL ID145089
CHEBI ID79968
SCHEMBL ID2477570
MeSH IDM0068954

Synonyms (59)

Synonym
n-desmethyl-selegiline
desmethyldeprenyl
desmethylselegiline
demethyl-deprenyl-dmd
demethyldeprenyl-selegiline
benzeneethanamine, alpha-methyl-n-2-propynyl-
1-phenyl-2-(n-2-propynyl)aminopropane
alpha-methyl-n-2-propynylbenzeneethanamine
di-n-propargylamphetamine
CHEMBL1276
1-phenyl-n-prop-2-ynylpropan-2-amine
AKOS012315520
FT-0665706
18913-84-3
FT-0673065
nordeprenyl
SCHEMBL4543249
n-(1-methyl-2-phenylethyl)-2-propyn-1-amine #
J-012201
n-propargylamphetamine
DTXSID30891483
benzeneethanamine, |a-methyl-n-2-propyn-1-yl-
EN300-146886
(1-phenylpropan-2-yl)(prop-2-yn-1-yl)amine
benzeneethanamine, alpha-methyl-n-2-propyn-1-yl-
(-)-n-demethyl deprenyl
CS-0068673
n-desmethyl selegiline-d5/ desmethyl deprenyl-d5
HY-119532
norselegiline
56862-28-3
LOPAC0_000461
NCGC00162161-01
NCGC00162161-02
chebi:79968 ,
CHEMBL145089
rnordeprenyl
n-[(2r)-1-phenylpropan-2-yl]prop-2-yn-1-amine
(2r)-1-phenyl-n-prop-2-ynylpropan-2-amine
unii-5f44wr1i53
5f44wr1i53 ,
n-((2r)-1-phenylpropan-2-yl)prop-2-yn-1-amine
AKOS006240224
CCG-204553
l-nordeprenyl
l-desmethyldeprenyl
n-desmethylselegiline
(-)-desmethylselegiline
(-)-n-desmethylselegiline
UUFAJPMQSFXDFR-LLVKDONJSA-N
((r)-1-methyl-2-phenyl-ethyl)-prop-2-ynyl-amine
selegiline hydrochloride impurity d [ep impurity]
benzeneethanamine, .alpha.-methyl-n-2-propyn-1-yl-, (.alpha.r)-
SCHEMBL2477570
[(2r)-1-phenylpropan-2-yl](prop-2-yn-1-yl)amine
Q27149135
SDCCGSBI-0050446.P002
desmethyl selegiline
DTXSID001315731

Drug Classes (1)

ClassDescription
amphetaminesAmines that constitute a class of central nervous system stimulants based on the structure of the parent amphetamine 1-phenylpropan-2-amine.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLS proteinHomo sapiens (human)Potency35.48130.35487.935539.8107AID624146
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency37.68580.035520.977089.1251AID504332
atrial natriuretic peptide receptor 1 precursorHomo sapiens (human)Potency8.49210.134610.395030.1313AID1347049
chromobox protein homolog 1Homo sapiens (human)Potency0.89130.006026.168889.1251AID488953
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Amine oxidase [flavin-containing] BRattus norvegicus (Norway rat)Activity0.00130.00080.00120.0014AID125378
Amine oxidase [flavin-containing] A Rattus norvegicus (Norway rat)Activity0.00120.00080.00110.0014AID125378; AID125701
Amine oxidase [flavin-containing] AMus musculus (house mouse)Activity0.00120.00060.00110.0014AID125378; AID125701
Amine oxidase [flavin-containing] BMus musculus (house mouse)Activity0.00110.00050.00100.0014AID125378; AID126675
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (27)

Assay IDTitleYearJournalArticle
AID229512Ratio of IC50 value against MAO-A to that of MAO-B.2002Journal of medicinal chemistry, Nov-21, Volume: 45, Issue:24
Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease.
AID126837In vitro inhibitory concentration against Monoamine oxidase B of rat brain homogenates; value ranges from 0.27-0.362002Journal of medicinal chemistry, Nov-21, Volume: 45, Issue:24
Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease.
AID125864In vitro inhibitory concentration against Monoamine oxidase A of rat brain homogenates; value ranges from 100-3402002Journal of medicinal chemistry, Nov-21, Volume: 45, Issue:24
Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347151Optimization of GU AMC qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347050Natriuretic polypeptide receptor (hNpr2) antagonism - Pilot subtype selectivity assay2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588378qHTS for Inhibitors of ATXN expression: Validation
AID1347058CD47-SIRPalpha protein protein interaction - HTRF assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347049Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot screen2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID504836Inducers of the Endoplasmic Reticulum Stress Response (ERSR) in human glioma: Validation2002The Journal of biological chemistry, Apr-19, Volume: 277, Issue:16
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.
AID1347045Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot counterscreen GloSensor control cell line2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347057CD47-SIRPalpha protein protein interaction - LANCE assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347405qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS LOPAC collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347059CD47-SIRPalpha protein protein interaction - Alpha assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347410qHTS for inhibitors of adenylyl cyclases using a fission yeast platform: a pilot screen against the NCATS LOPAC library2019Cellular signalling, 08, Volume: 60A fission yeast platform for heterologous expression of mammalian adenylyl cyclases and high throughput screening.
AID125701The ability of the compound(25 umol/kg/day) to inactivate monoamine oxidase A(MAO-A) was tested on brain mitochondrial membranes of mice, for 3 day.1996Journal of medicinal chemistry, Nov-22, Volume: 39, Issue:24
Synthesis and selective monoamine oxidase B-inhibiting properties of 1-methyl-1,2,3,6-tetrahydropyrid-4-yl carbamate derivatives: potential prodrugs of (R)- and (S)-nordeprenyl.
AID126675The ability of the compound(25 umol/kg/day) to inactivate monoamine oxidase B (MAO-B) was tested on brain mitochondrial membranes of mice, for 3 day.1996Journal of medicinal chemistry, Nov-22, Volume: 39, Issue:24
Synthesis and selective monoamine oxidase B-inhibiting properties of 1-methyl-1,2,3,6-tetrahydropyrid-4-yl carbamate derivatives: potential prodrugs of (R)- and (S)-nordeprenyl.
AID230685Ratio of activities of MAO-B / MAO-A1996Journal of medicinal chemistry, Nov-22, Volume: 39, Issue:24
Synthesis and selective monoamine oxidase B-inhibiting properties of 1-methyl-1,2,3,6-tetrahydropyrid-4-yl carbamate derivatives: potential prodrugs of (R)- and (S)-nordeprenyl.
AID235091Residual activity was obtained.1996Journal of medicinal chemistry, Nov-22, Volume: 39, Issue:24
Synthesis and selective monoamine oxidase B-inhibiting properties of 1-methyl-1,2,3,6-tetrahydropyrid-4-yl carbamate derivatives: potential prodrugs of (R)- and (S)-nordeprenyl.
AID125378The ability of the compound(25 umol/kg/day) to inactivate monoamine oxidase (MAO) was tested on brain mitochondrial membranes of mice, for 3 days.1996Journal of medicinal chemistry, Nov-22, Volume: 39, Issue:24
Synthesis and selective monoamine oxidase B-inhibiting properties of 1-methyl-1,2,3,6-tetrahydropyrid-4-yl carbamate derivatives: potential prodrugs of (R)- and (S)-nordeprenyl.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (53)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's18 (33.96)18.2507
2000's23 (43.40)29.6817
2010's7 (13.21)24.3611
2020's5 (9.43)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials12 (28.57%)5.53%
Trials0 (0.00%)5.53%
Reviews1 (2.38%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other29 (69.05%)84.16%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (2)

ArticleYear
Deprenyl and desmethylselegiline protect mesencephalic neurons from toxicity induced by glutathione depletion.
The Journal of pharmacology and experimental therapeutics, Volume: 284, Issue: 2
1998
L-(-)-desmethylselegiline, a metabolite of selegiline [L-(-)-deprenyl], protects mesencephalic dopamine neurons from excitotoxicity in vitro.
Journal of neurochemistry, Volume: 68, Issue: 1
1997
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (10)

ArticleYear
Pharmacokinetics of selegiline, R-methamphetamine, R-amphetamine, and desmethylselegiline in oral fluid after a single oral administration of selegiline.
Drug testing and analysis, Volume: 11, Issue: 6
2019
Pharmacokinetic studies of (-)-deprenyl and some of its metabolites in mouse.
Journal of neural transmission. Supplementum, Issue: 72
2007
Effect of concomitant hormone replacement therapy containing estradiol and levonorgestrel on the pharmacokinetics of selegiline.
European journal of clinical pharmacology, Volume: 58, Issue: 4
2002
Selegiline pharmacokinetics are unaffected by the CYP3A4 inhibitor itraconazole.
European journal of clinical pharmacology, Volume: 57, Issue: 1
2001
Dose linearity study of selegiline pharmacokinetics after oral administration: evidence for strong drug interaction with female sex steroids.
British journal of clinical pharmacology, Volume: 47, Issue: 3
1999
Pharmacokinetic evaluation of a selegiline pulsatile oral delivery system.
Biopharmaceutics & drug disposition, Volume: 18, Issue: 8
1997
Integrated pharmacokinetic and metabolic modeling of selegiline and metabolites after transdermal administration.
Biopharmaceutics & drug disposition, Volume: 18, Issue: 7
1997
Pharmacokinetics and bioequivalence of the main metabolites of selegiline: desmethylselegiline, methamphetamine and amphetamine after oral administration of selegiline.
International journal of clinical pharmacology and therapeutics, Volume: 35, Issue: 1
1997
Lack of pharmacokinetic interaction between the selective dopamine agonist cabergoline and the MAO-B inhibitor selegiline.
Journal of neural transmission. Supplementum, Volume: 45
1995
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (7)

ArticleYear
Pharmacokinetic studies of (-)-deprenyl and some of its metabolites in mouse.
Journal of neural transmission. Supplementum, Issue: 72
2007
Dose linearity study of selegiline pharmacokinetics after oral administration: evidence for strong drug interaction with female sex steroids.
British journal of clinical pharmacology, Volume: 47, Issue: 3
1999
Pharmacokinetic evaluation of a selegiline pulsatile oral delivery system.
Biopharmaceutics & drug disposition, Volume: 18, Issue: 8
1997
Desmethylselegiline, a metabolite of selegiline, is an irreversible inhibitor of monoamine oxidase type B in humans.
Journal of clinical pharmacology, Volume: 37, Issue: 7
1997
Pharmacokinetics and bioequivalence of the main metabolites of selegiline: desmethylselegiline, methamphetamine and amphetamine after oral administration of selegiline.
International journal of clinical pharmacology and therapeutics, Volume: 35, Issue: 1
1997
Absorption and presystemic metabolism of selegiline hydrochloride at different regions in the gastrointestinal tract in healthy males.
Pharmaceutical research, Volume: 13, Issue: 10
1996
Bioequivalence evaluation of two preparations containing the highly variable compound selegiline (L-deprenyl).
International journal of clinical pharmacology and therapeutics, Volume: 34, Issue: 10
1996
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (8)

ArticleYear
A phase 1 trial of pharmacologic interactions between transdermal selegiline and a 4-hour cocaine infusion.
BMC clinical pharmacology, Aug-01, Volume: 9
2009
Protective effects of selegiline and desmethylselegiline against N-methyl-D-aspartate-induced rat retinal damage.
European journal of pharmacology, Jan-01, Volume: 458, Issue: 1-2
2003
Stereoselective analyses of selegiline metabolites: possible urinary markers for selegiline therapy.
Forensic science international, Apr-26, Volume: 101, Issue: 2
1999
Dose linearity study of selegiline pharmacokinetics after oral administration: evidence for strong drug interaction with female sex steroids.
British journal of clinical pharmacology, Volume: 47, Issue: 3
1999
Pharmacokinetic evaluation of a selegiline pulsatile oral delivery system.
Biopharmaceutics & drug disposition, Volume: 18, Issue: 8
1997
Absorption and presystemic metabolism of selegiline hydrochloride at different regions in the gastrointestinal tract in healthy males.
Pharmaceutical research, Volume: 13, Issue: 10
1996
An enzymatic assay for the MAO-B inhibitor selegiline in plasma.
Journal of pharmaceutical and biomedical analysis, Volume: 12, Issue: 7
1994
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Interactions (1)

ArticleYear
Dose linearity study of selegiline pharmacokinetics after oral administration: evidence for strong drug interaction with female sex steroids.
British journal of clinical pharmacology, Volume: 47, Issue: 3
1999
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]