2-Amino-1-phenyl-1-propanol

Details

• Internal ID: 85679a97-c420-4add-a10d-591259f3ed53
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylpropanes
• IUPAC Name: 2-amino-1-phenylpropan-1-ol
• SMILES (Canonical): CC(C(C1=CC=CC=C1)O)N
• SMILES (Isomeric): CC(C(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
• InChI Key: DLNKOYKMWOXYQA-UHFFFAOYSA-N
• Popularity: 2,005 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): 46.20 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.07
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 2-Amino-1-phenyl-1-propanol
• (1S,2R)-(+)-Norephedrine
• 48115-38-4
• 2-amino-1-phenylpropan-1-ol
• alpha-(1-aminoethyl)benzyl alcohol
• Propadrine
• NSC-120735
• UNII-683H0R9659
• 2-Amino-2-methyl-1-phenylethanol
• 2-Amino-1-hydroxy-1-phenylpropane
• beta-Hydroxy-alpha-methylphenethylamine
• Benzenemethanol, alpha-(1-aminoethyl)-
• Benzenemethanol, .alpha.-(1-aminoethyl)-
• 683H0R9659
• 14838-15-4
• Bencenometanol
• Phenylfenesin
• Cathina
• Minusine
• Rinexin
• Fansia
• d-norisoephedrine
• Fenilpropanolamina
• Norpseudoephedrine
• Phenylpropanolamina
• (+)-Norephedrin
• Phenylpropanolaminum
• l-Nor-psi-ephedrin
• d-Phenylpropanolamine
• l-Nor-psi-ephedrine
• 37577-28-9
• D-(+)-Norephedrine
• TAVIST-D
• Cathina [INN-Spanish]
• Norefedrina, (+-)-
• (+-)-Fenilpropanolamina
• Norephedrine, (.+.)-
• Phenylpropanolamine (VAN)
• PPA [Nasal Decongestant]
• Norpseudoephedrine, (+)-
• (+/-)-Phenylpropanolamine
• Norephedrine (+-)-(8CI)
• Phenylpropanolamine [INN:BAN]
• CHEMBL136560
• HSDB 6485
• Phenylpropanolaminum [INN-Latin]
• 2-Amino-1-phenyl-1-propanol #
• Phenylpropanolamina [INN-Spanish]
• NSC 9920
• NSC-9920
• EINECS 207-754-1
• EINECS 211-850-9
• EINECS 238-900-2
• EINECS 253-014-6
• Benzenemethanol, .alpha.-[(1R)-1-aminoethyl]-, (.alpha.R)-rel-
• erythro-2-Amino-1-phenyl-1-propanol
• dl-alpha-(1-Aminoethyl)benzyl alcohol
• Benzyl alcohol, alpha-(1-aminoethyl)-
• BRN 2802895
• BRN 3196918
• dl-alpha-Hydroxy-beta-aminopropylbenzene
• (1RS,2SR)-2-amino-1-phenyl-1-propanol
• D-threo-2-amino-1-hydroxy-1-phenylpropane
• Norephedrine, (+)
• Norephedrine, (-)
• (R*,R*)-alpha-(1-Aminoethyl)benzyl alcohol
• Benzenemethanol alpha-(1-aminoethyl)-(R* S*)-
• (R*,S*)-(+-)-alpha-(1-aminoethyl)benzyl alcohol
• Benzenemethanol, alpha-(1-aminoethyl)-, (R*,S*)-
• 1-phenyl-2-aminopropanol
• (alpha S)-alpha-[(1S)-1-Aminoethyl]benzenemethanol
• Benzenemethanol alpha-(1-aminoethyl)-(R*S*)-(+-)-
• (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-
• Benzenemethanol, .alpha.-(1-aminoethyl)-, [R-(R*,S*)]-
• SCHEMBL98589
• Benzenemethanol, .alpha.-(1-aminoethyl)-, (R*,S*)-(.+-.)-
• Benzenemethanol, .alpha.-(1-aminoethyl)-, (R*,S*)-(.+.)-
• Norephedrine, (.+/-.)-
• CHEMBL61006
• DivK1c_000795
• bencenometanol,. Alfa .-(1-aminoetil)-, (R *, S *)-(+-)-
• Benzenemethanol, .alpha.-[(1R)-1-aminoethyl]-, (.alpha.S)-rel-
• 2-amino-1-phenylpropane-1-ol
• (1s, 2r)-(+)-norephedrine
• 2-Amino-1-phenyl-propan-1-ol
• (1 S,2R)-(+)-norephedrine
• KBio1_000795
• DTXSID70859305
• NINDS_000795
• (1S, 2R )-(+)-norephedrine
• (+)2-Amino-1-phenyl-propan-1-ol
• BDBM50022722
• NSC120735
• AKOS015891154
• IDI1_000795
• Pseudonorephedrine, (+) [cathine, (+)]
• Pseudonorephedrine, (-) [cathine, (-)]
• (1R, 2R)-2-Amino-1-phenyl-propan-1-ol
• (1R, 2S)-2-Amino-1-phenyl-propan-1-ol
• (1S, 2R)-2-Amino-1-phenyl-propan-1-ol
• (1S, 2S)-2-Amino-1-phenyl-propan-1-ol
• L001077
• Benzenemethanol, .alpha.-(1-aminoethyl)-, (R*,S*)-(.+/-.)-

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:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1867	P08913	Alpha-2a adrenergic receptor	275.42 nM	Ki	PMID: 15163201

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 equisetina
• Ephedra intermedia
• Ephedra sinica
• Thymus quinquecostatus
• Thymus vulgaris

Cross-Links

• PubChem: 4786
• NPASS: NPC164514
• ChEMBL: CHEMBL61006
• LOTUS: LTS0258991
• wikiData: Q97786582