Molecule

(+)-Norephedrine

AlkaPlorer ID: AK008658

Synonym: 'Norephedrine', '', 'pseudonorephedrine', 'Mucorama', 'DL-Phenylpropanolamine', 'L-Phenyl Propanolamine', 'd-Norephedrine', 'Obestat', '(+)-Norephedrine', 'norpseudoephedrine', '(+)-Norpseudoephedrine', 'Prestwick_388', 'Propadrine', 'Nobese', 'Cathine', 'Hydriatine', 'L-NOREPHEDRINE', 'D-Cathine', 'DL-Norephedrine'

IUPAC Name: [(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]azanium

Structure

SMILES: C[C@H]([NH3+])[C@H](O)C1=CC=CC=C1

InChI: InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/p+1/t7-,9-/m0/s1

InChIKey: DLNKOYKMWOXYQA-CBAPKCEASA-O

Reference

Simultaneous determination of and var. alkaloids by ion-pair chromatography

PubChem CID: 6931753

LOTUS: LTS0188366

SuperNatural Ⅲ: SN0068969-02

NPASS: NPC290515

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Eulophia spectabilis	Eulophia	Orchidaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Ephedra distachya	Ephedra	Ephedraceae	Ephedrales	Gnetopsida	Streptophyta	Viridiplantae	Eukaryota
Bupleurum sibiricum	Bupleurum	Apiaceae	Apiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Ephedra gerardiana	Ephedra	Ephedraceae	Ephedrales	Gnetopsida	Streptophyta	Viridiplantae	Eukaryota
Thymus vulgaris	Thymus	Lamiaceae	Lamiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Ephedra intermedia	Ephedra	Ephedraceae	Ephedrales	Gnetopsida	Streptophyta	Viridiplantae	Eukaryota
Berberis empetrifolia	Berberis	Berberidaceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Ephedra sinica	Ephedra	Ephedraceae	Ephedrales	Gnetopsida	Streptophyta	Viridiplantae	Eukaryota
Ephedra equisetina	Ephedra	Ephedraceae	Ephedrales	Gnetopsida	Streptophyta	Viridiplantae	Eukaryota
Thymus quinquecostatus	Thymus	Lamiaceae	Lamiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Allium atroviolaceum	Allium	Amaryllidaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Stylissa massa	Stylissa	Axinellidae	Axinellida	Demospongiae	Porifera	Metazoa	Eukaryota

Properties Information

Molecule Weight: 152.21699999999998

TPSA？: 47.870000000000005

MolLogP？: 0.3503999999999995

Number of H-Donors: 2

Number of H-Acceptors: 1

RingCount: 1

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bos taurus	Phenylethanolamine N-methyltransferase	Km	1310000.0	nM	10.1021/jm00118a021
Canis lupus familiaris	Canis familiaris	ED20	330.0	nM kg-1	10.1021/jm025550h
Canis lupus familiaris	Canis familiaris	ED5	1100.0	nM kg-1	10.1021/jm025550h
Homo sapiens	Adrenergic receptors; alpha-1 A & B	Selectivity	1.0	None	10.1021/jm025550h
Homo sapiens	Alpha-1a adrenergic receptor	EC50	230000.0	nM	10.1021/jm025550h
Homo sapiens	Alpha adrenergic receptor (1a and 1d)	Selectivity	0.3	None	10.1021/jm025550h
Homo sapiens	Alpha adrenergic receptor (1a and 1d)	Selectivity	1.0	None	10.1021/jm025550h
Homo sapiens	Solute carrier organic anion transporter family member 1B1	Inhibition	97.41	%	10.1124/mol.112.084152
Homo sapiens	Solute carrier organic anion transporter family member 1B3	Inhibition	87.0	%	10.1124/mol.112.084152
Mesocricetus auratus	Alpha-1b adrenergic receptor	Ki	9600.0	nM	10.1021/jm025550h
Oryctolagus cuniculus	Oryctolagus cuniculus	Efficacy	68.0	%	10.1021/jm025550h
Rattus norvegicus	Alpha-1a adrenergic receptor	Ki	9800.0	nM	10.1021/jm025550h
Rattus norvegicus	Alpha-1b adrenergic receptor	EC50	280000.0	nM	10.1021/jm025550h
Rattus norvegicus	Alpha-1d adrenergic receptor	EC50	58000.0	nM	10.1021/jm025550h
Rattus norvegicus	Alpha-1d adrenergic receptor	Ki	8400.0	nM	10.1021/jm025550h
Rattus norvegicus	Rattus norvegicus	Efficacy	34.0	%	10.1021/jm025550h
Rattus norvegicus	Rattus norvegicus	Efficacy	91.0	%	10.1021/jm025550h
Rattus norvegicus	Serotonin (5-HT) receptor	pA2	nan	None	10.1021/jm00177a017
None	ADMET	Ratio	0.017	None	10.1021/jm00118a021
None	ADMET	Vmax	0.22	nM/mg*min	10.1021/jm00118a021
None	Hepatotoxicity	Hepatotoxicity	nan	None	10.1021/tx900326k
None	Unchecked	Ratio	0.4	None	10.1021/jm025550h

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT013667	C[C@H](N)C(=O)c1ccccc1>>C[C@H](N)[C@H](O)c1ccccc1	RXN-9339
AKRT013681	C[C@H](N)Cc1ccccc1>>C[C@H](N)[C@H](O)c1ccccc1	RXN-19390
AKRT014582	C[SAH].C[C@H](N)[C@H](O)c1ccccc1>>CN[C@@H](C)[C@H](O)c1ccccc1	RXN-9341