Norephedrine

Details

• Internal ID: 47c393a9-d60c-441f-85d8-5f4061d42b72
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylpropanes
• IUPAC Name: (1S,2R)-2-amino-1-phenylpropan-1-ol
• SMILES (Canonical): CC(C(C1=CC=CC=C1)O)N
• SMILES (Isomeric): C[C@H]([C@H](C1=CC=CC=C1)O)N
• InChI: InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m1/s1
• InChI Key: DLNKOYKMWOXYQA-VXNVDRBHSA-N
• Popularity: 2,629 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21 g/mol
• Exact Mass: 151.099714038 g/mol
• Topological Polar Surface Area (TPSA): 46.30 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.07
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• phenylpropanolamine
• (+)-Norephedrine
• Rhindecon
• dl-Norephedrine
• Dexatrim
• Propagest
• Mucron
• d-Norephedrine
• (1S,2R)-2-amino-1-phenylpropan-1-ol
• Super Odrinex
• Propadrine
• 1r,2s-phenylpropylamine
• (+-)-Norephedrin
• dl-Phenylpropanolamine
• Cathinum [INN-Latin]
• (+)-phenylpropanolamine
• 37577-28-9
• dl-1-Phenyl-2-aminopropanol-1
• (1s,2r)-norephedrine
• 14838-15-4
• d-Phenylpropanolamine
• dl-2-Amino-1-hydroxy-1-phenylpropane
• CHEBI:36
• D-(+)-Norephedrine
• Phenylfenesin
• Cathina
• Minusine
• Fenilpropanolamina
• Norpseudoephedrine
• NSC9920
• Phenylpropanolamina
• (+)-Norephedrin
• Phenylpropanolaminum
• UNII-7875H6443P
• l-Nor-psi-ephedrin
• l-Nor-psi-ephedrine
• Cathina [INN-Spanish]
• 7875H6443P
• Phenylpropanolamine (VAN)
• PPA [Nasal Decongestant]
• Bencenometanol
• Fansia
• Phenylpropanolamine [INN:BAN]
• d-norisoephedrine
• Fugoa Depot
• HSDB 6485
• Benzenemethanol, alpha-(1-aminoethyl)-, (S-(R*,S*))-
• Phenylpropanolaminum [INN-Latin]
• Phenyldrine
• Phenylpropanolamina [INN-Spanish]
• Acutrim
• Codimal
• Contuss
• Guaipax
• Myminic
• Partuss
• Phenoxine
• Snaplets
• Conex
• Despec
• Gentab
• Nolex
• Rhymed
• Vanex
• NSC 9920
• EINECS 207-754-1
• EINECS 211-850-9
• EINECS 238-900-2
• Fansia (TN)
• Dura-Vent
• erythro-2-Amino-1-phenyl-1-propanol
• dl-alpha-(1-Aminoethyl)benzyl alcohol
• Fugoa
• Ami-Tex
• Benzyl alcohol, alpha-(1-aminoethyl)-
• BRN 2802895
• BRN 3196918
• dl-alpha-Hydroxy-beta-aminopropylbenzene
• (+/-)-Norephedrine
• TAVIST-D
• Norefedrina, (+-)-
• (+-)-Fenilpropanolamina
• Norephedrine, (.+.)-
• (+/-)-Norephedrin
• Prestwick_388
• (+/-)-Phenylpropanolamine
• Norephedrine (+-)-(8CI)
• Benzenemethanol, alpha-(1-aminoethyl)-, (R*,S*)-
• DEA No. 1230
• Benzenemethanol, alpha-(1-aminoethyl)-, (R*,S*)-(+-)-
• NSC-9920
• EINECS 253-014-6
• Norephedrine, (.+-.)-
• Propalin (TN)
• (1RS,2SR)-2-amino-1-phenyl-1-propanol
• D-threo-2-amino-1-hydroxy-1-phenylpropane
• Proin (TN)
• (R*,R*)-alpha-(1-Aminoethyl)benzyl alcohol
• L-(-)-Norephedrine
• L-Phenyl Propanolamine
• Benzenemethanol alpha-(1-aminoethyl)-(R* S*)-
• SpecPlus_000934
• (.+-.)-Norephedrine
• (R*,S*)-(+-)-alpha-(1-aminoethyl)benzyl alcohol
• Prestwick3_000324
• Spectrum2_000516
• Spectrum3_001706
• Spectrum4_001685
• Spectrum5_000330
• 1s,2r-phenylpropanolamine
• (alpha S)-alpha-[(1S)-1-Aminoethyl]benzenemethanol
• Benzenemethanol alpha-(1-aminoethyl)-(R*S*)-(+-)-
• DEA Code 1225
• D04KKT
• D09JXM
• WLN: ZY1&YQR
• (alpha S)-rel-alpha-[(1R)-1-Aminoethyl]benzenemethanol
• Benzenemethanol, .alpha.-(1-aminoethyl)-, (R*,R*)-
• Benzenemethanol, alpha-(1-aminoethyl)-, (S-(R*,R*))-
• 1 Bencenometanol, Alfa-[(1R)-aminoetil]-, (Alfa S)-rel-
• Constituent of "Khat" plant
• SCHEMBL26905
• (.+-.)-Phenylpropanolamine
• BSPBio_000327
• BSPBio_003292
• KBioGR_001950
• Benzenemethanol, .alpha.-(1-aminoethyl)-, (R*,S*)-(.+-.)-
• Benzenemethanol, .alpha.-(1-aminoethyl)-, (R*,S*)-(.+.)-
• Benzenemethanol, alpha-((1R)-1-aminoethyl)-, (alphaS)-rel-
• (+)-(1s,2r)-norephedrine
• (1s,2r)-(-)-norephedrine
• BIDD:GT0376
• DivK1c_007030
• SPECTRUM2300253
• SPBio_000471
• bencenometanol,. Alfa .-(1-aminoetil)-, (R *, S *)-(+-)-
• Benzenemethanol, .alpha.-[(1R)-1-aminoethyl]-, (.alpha.R)-rel-
• Benzenemethanol, .alpha.-[(1R)-1-aminoethyl]-, (.alpha.S)-rel-
• PHENYLPROPANOLAMINE, D-
• BPBio1_000361
• CHEMBL2092846
• DTXSID4023466
• KBio1_001974
• KBio3_002512
• Phenylpropanolamine (Norephedrine)
• DTXSID301313960
• PHENYLPROPANOLAMINE, (+)-
• (1S,2R)-(+)-Phenylpropanolamine
• 700-65-2
• (1S,2R)-PHENYLPROPANOLAMINE
• norpseudoephedrine, (R*,S*)-isomer
• BDBM50405613
• CCG-39586
• PDSP1_001348
• PDSP2_001332
• AKOS027322360
• (1S,2R)-(+)-Norephedrine, 98%
• SDCCGMLS-0066900.P001
• Benzenemethanol, (R*,S*)-(.+-.)-
• L-.alpha.-(1-Aminoethyl)benzyl alcohol
• NCGC00178157-01
• NCGC00178157-02
• DL-.alpha.-(1-aminoethyl)benzyl alcohol
• LS-97285
• LS-97462
• norpseudoephedrine, (S-(R*,R*))-isomer
• ULR
• Benzyl alcohol, .alpha.-(1-amino-ethyl)
• (1S,2R)-2-AMINO-1-PHENYLPROPANOL
• LS-176795
• AB00375975
• N0631
• DL-.alpha.-hydroxy-.beta.-aminopropylbenzene
• (1S,2R)-(+)-2-Amino-1-phenyl-1-propanol
• C02343
• AB00375975_05
• Q413147
• J-501786
• (1r,2s)-2-hydroxy-2-phenyl-1-methyl-1-aminoethane
• BRD-K27853494-001-02-5
• BRD-K27853494-003-04-7
• BENZENEMETHANOL, .ALPHA.-((1R)-1-AMINOETHYL)-, (.ALPHA.S)-
• 27818-48-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9940	99.40%
Caco-2	+	0.8230	82.30%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Lysosomes	0.7779	77.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9700	97.00%
OATP1B3 inhibitior	+	0.9672	96.72%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9277	92.77%
P-glycoprotein inhibitior	-	0.9898	98.98%
P-glycoprotein substrate	-	0.9566	95.66%
CYP3A4 substrate	-	0.8163	81.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5398	53.98%
CYP3A4 inhibition	-	0.9261	92.61%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9909	99.09%
CYP inhibitory promiscuity	-	0.9096	90.96%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	+	0.5189	51.89%
Carcinogenicity (trinary)	Non-required	0.6955	69.55%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.5969	59.69%
Skin corrosion	+	0.6347	63.47%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8453	84.53%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.5823	58.23%
skin sensitisation	-	0.6653	66.53%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	-	0.6222	62.22%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	III	0.8360	83.60%
Estrogen receptor binding	-	0.9615	96.15%
Androgen receptor binding	-	0.8441	84.41%
Thyroid receptor binding	-	0.8574	85.74%
Glucocorticoid receptor binding	-	0.8410	84.10%
Aromatase binding	-	0.9400	94.00%
PPAR gamma	-	0.8746	87.46%
Honey bee toxicity	-	0.9742	97.42%
Biodegradation	-	1.0000	100.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	-	0.8504	85.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.69%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.42%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	91.65%	90.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.04%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.88%	95.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	89.35%	94.08%
CHEMBL3492	P49721	Proteasome Macropain subunit	85.06%	90.24%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.08%	91.11%
CHEMBL3902	P09211	Glutathione S-transferase Pi	82.80%	93.81%
CHEMBL4208	P20618	Proteasome component C5	82.54%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.38%	85.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.00%	93.56%

Plants that contains it

• Catha edulis
• Ephedra distachya
• Ephedra equisetina
• Ephedra intermedia
• Ephedra minuta
• Ephedra sinica
• Thymus quinquecostatus
• Thymus vulgaris

Cross-Links

• PubChem: 26934
• NPASS: NPC226096
• LOTUS: LTS0093784
• wikiData: Q413147