Page last updated: 2024-11-08

norpseudoephedrine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

norpseudoephedrine: major metabolite of diethylpropion in man under acidic urine conditions; RN given refers to cpd without isomeric designation; [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cathine : An amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1S,2S-stereoisomer). [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]

Cross-References

ID SourceID
PubMed CID441457
CHEMBL ID1412041
CHEBI ID4109
SCHEMBL ID34132
MeSH IDM0046817

Synonyms (96)

Synonym
benzenemethanol, .alpha.-[(1s)-1-aminoethyl]-, (.alpha.s)-
benzenemethanol, .alpha.-(1-aminoethyl)-, [s-(r*,r*)]-
norpseudoephedrine, (+)-
einecs 253-014-6
brn 2802895
(r*,r*)-alpha-(1-aminoethyl)benzyl alcohol
norpseudoephedrine
cathinum [inn-latin]
threo-1-phenyl-1-hydroxy-2-aminopropane
racemic norpseudoephedrine
cathina [inn-spanish]
minusine
l-nor-psi-ephedrin [german]
threo-2-amino-1-hydroxy-1-phenylpropane
l-nor-psi-ephedrine
exponcit
benzenemethanol, alpha-((1r)-1-aminoethyl)-, (alphar)-rel-
benzenemethanol, alpha-((1s)-1-aminoethyl)-, (alphas)-
einecs 207-754-1
benzenemethanol, alpha-(1-aminoethyl)-, (r*,r*)-
dea no. 1230
cathine [inn]
cas-154-41-6
NCGC00016416-01
cathine (inn)
D07627
PDSP2_001337
37577-28-9
C08300
cathine
492-39-7
d-cathine
(+)-norpseudoephedrine
d-nor-psi-ephedrine
katine
d-norpseudoephedrine
pseudonorephedrine
psi-norephedrine
DB01486
PDSP1_001353
(1s,2s)-(+)-norpseudoephedrine
(1s,2s)-2-amino-1-phenylpropan-1-ol
36393-56-3
(1s,2s)-2-amino-1-phenyl-propan-1-ol
A823766
dl-nor-psi-ephedrine
niosh/rc9110000
RC91100000 ,
norpseudoephedrine, (+-)-
threo-2-amino-1-phenylpropan-1-ol
phenylpropanolamine d-threo-form
(1s,2s)-pseudonorephedrine
chebi:4109 ,
CHEMBL1412041
.omega.-norephedrine
norpseudoephedrine, d-
l-nor-psi-ephedrin
unii-27a0hlc3hh
27a0hlc3hh ,
4-13-00-01874 (beilstein handbook reference)
unii-e1l4zw2f8o
e1l4zw2f8o ,
constituent of khat plant
cathina
cathinum
bdbm50405615
d-phenylpropanolamine
(+)-norephedrin
d-(+)-norpseudoephedrine
AKOS015891205
catina
norpseudoephedrine [mi]
cathine [mart.]
benzenemethanol, .alpha.-(1-aminoethyl)-, (s-(r*,r*))-
(1s,2s)-2-amino-1-phenyl-1-propanol
benzenemethanol, .alpha.-((1s)-1-aminoethyl)-, (.alpha.s)-
phenylpropanolamine d-threo-form [mi]
cathine [who-dd]
d-(+)-norephedrine
SCHEMBL34132
J-500428
(+)-pseudonorephedrine
d-norpseudoephedrin
nor-psi-ephedrine
cathin
2-amino-1-phenyl-1-propanol, (+)- #
(+/-)-norpseudoephedrine
cathine, (+/-)-
benzenemethanol, .alpha.-((1r)-1-aminoethyl)-, (.alpha.r)-rel-
(1s,2s)-(+)-norpseudoephedrine, >=98.0% (nt)
d-norpseudoephedrine (d-cathine)
Q423797
AS-30504
DTXSID20889399
DTXSID50889347
492-39-7 (free base)

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"3 mg cathine), but no suspected unexpected serious adverse reactions were noted."( Efficacy and Safety of Cathine (Nor-Pseudoephedrine) in the Treatment of Obesity: A Randomized Dose-Finding Study.
Blüher, M; Chen-Stute, A; Hastreiter, L; Hauner, H; Scholze, J; Werdier, D, 2017
)
0.46

Pharmacokinetics

ExcerptReferenceRelevance
" The data were evaluated using computerized pharmacokinetic compartmental analysis."( Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves.
Harder, S; Kauert, GF; Niess, C; Schramm, M; Toennes, SW, 2003
)
0.32
" Compared with single-herb extracts, alkaloids in plasma (except methylephedrine, benzoylmesaconine and benzoylhypaconine) showed slower elimination (the mean residence time or half-life was longer), although the maximum plasma concentration and area under the plasma concentration curve values decreased."( Simultaneous quantification and pharmacokinetics of alkaloids in Herba Ephedrae-Radix Aconiti Lateralis extracts.
Huo, H; Li, H; Luo, J; Song, S; Tang, Q; Xing, X,
)
0.13

Dosage Studied

ExcerptRelevanceReference
" Thus, different dose-response curves were generated depending upon whether cathine or vehicle was administered the day before testing."( Discriminative stimulus properties of (+)cathine, an alkaloid of the khat plant.
Pehek, EA; Schechter, MD, 1990
)
0.28
" Prior reserpinization did not significantly shift the cumulative dose-response curves for l-NOR and PPA."( Cardiovascular differences between phenylpropanolamine and its related norephedrine isomers in the rat.
Kiritsy, PJ; Maher, TJ; Moya-Huff, FA, 1987
)
0.27
"Although there is a rich body of research available regarding the effect of acute and chronic khat dosing in animal models, research on the behavioral and cognitive effects of khat in human subjects is not extensive and several of the available studies have been done only in the context of observational and single-case studies."( Khat use and neurobehavioral functions: suggestions for future studies.
Al'Absi, M; Hoffman, R, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
central nervous system stimulantAny drug that enhances the activity of the central nervous system.
psychotropic drugA loosely defined grouping of drugs that have effects on psychological function.
[role 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]

Drug Classes (2)

ClassDescription
amphetaminesAmines that constitute a class of central nervous system stimulants based on the structure of the parent amphetamine 1-phenylpropan-2-amine.
phenethylamine alkaloid
[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 (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Ferritin light chainEquus caballus (horse)Potency0.25125.623417.292931.6228AID485281
hypoxia-inducible factor 1, alpha subunit (basic helix-loop-helix transcription factor)Homo sapiens (human)Potency6.30960.00137.762544.6684AID914; AID915
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency0.12590.251215.843239.8107AID504327
lamin isoform A-delta10Homo sapiens (human)Potency7.94330.891312.067628.1838AID1487
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Phenylethanolamine N-methyltransferaseBos taurus (cattle)Ki3,700.00000.00312.329310.0000AID156054
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
methylationPhenylethanolamine N-methyltransferaseBos taurus (cattle)
epinephrine biosynthetic processPhenylethanolamine N-methyltransferaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (1)

Processvia Protein(s)Taxonomy
phenylethanolamine N-methyltransferase activityPhenylethanolamine N-methyltransferaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID781325pKa (acid-base dissociation constant) as determined by Liao ref: J Chem Info Model 20092014Pharmaceutical research, Apr, Volume: 31, Issue:4
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.
AID156054In vitro binding affinity of compound towards bovine adrenal phenylethanolamine N-methyl-transferase (PNMT)1988Journal of medicinal chemistry, Oct, Volume: 31, Issue:10
Stereochemical aspects of phenylethanolamine analogues as substrates of phenylethanolamine N-methyltransferase.
AID1442400Induction of stimulus generalization in Sprague-Dawley rat trained to discriminate rac-cathinone assessed as appropriate responding level to training drug by two lever method2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (119)

TimeframeStudies, This Drug (%)All Drugs %
pre-199043 (36.13)18.7374
1990's21 (17.65)18.2507
2000's19 (15.97)29.6817
2010's31 (26.05)24.3611
2020's5 (4.20)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 36.37

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index36.37 (24.57)
Research Supply Index4.90 (2.92)
Research Growth Index4.53 (4.65)
Search Engine Demand Index53.49 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (36.37)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (4.72%)5.53%
Reviews6 (4.72%)6.00%
Case Studies8 (6.30%)4.05%
Observational0 (0.00%)0.25%
Other107 (84.25%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]