Ephedrine

Details

• Internal ID: 6e8ecd26-8f63-4173-9504-4e682c9e3eab
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylpropanes
• IUPAC Name: (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
• SMILES (Canonical): CC(C(C1=CC=CC=C1)O)NC
• SMILES (Isomeric): C[C@@H]([C@@H](C1=CC=CC=C1)O)NC
• InChI: InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1
• InChI Key: KWGRBVOPPLSCSI-WPRPVWTQSA-N
• Popularity: 15,636 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23 g/mol
• Exact Mass: 165.115364102 g/mol
• Topological Polar Surface Area (TPSA): 32.30 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• l-Ephedrine
• (-)-Ephedrine
• 299-42-3
• Ephedrin
• L(-)-Ephedrine
• Lexofedrin
• Ephedrol
• Mandrin
• Sanedrine
• Fedrin
• I-Sedrin
• 1-Sedrin
• Biophedrin
• Ephedral
• Ephedremal
• Ephedrital
• Ephedrosan
• Ephedrotal
• Ephedsol
• Ephendronal
• Ephoxamin
• Kratedyn
• Manadrin
• Vencipon
• Eciphin
• Efedrin
• Zephrol
• Nasol
• Sal-Phedrine
• Ephedrine l-form
• (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
• Xenadrine
• Norephedrine, N-methyl-
• Ephedrine [USAN:BAN]
• Ephedrine, anhydrous
• Ephedrine, L-(-)-
• (L)-EPHEDRINE
• HSDB 3072
• l-2-Methylamino-1-phenylpropanol
• l-alpha-(1-Methylaminoethyl)benzyl alcohol
• NSC 8971
• EINECS 206-080-5
• racephedrine
• Ephedrine (TN)
• UNII-GN83C131XS
• Ephedrine (USP)
• l-Erythro-2-(methylamino)-1-phenylpropan-1-ol
• NSC 170951
• 1-Phenyl-2-methylaminopropanol
• Ephedrinum, anhydrous
• GN83C131XS
• CHEBI:15407
• AI3-02761
• 1-2-Methylamino-1-phenylpropanol
• (-)-alpha-(1-Methylaminoethyl)benzyl alcohol
• 2-Methylamino-1-phenyl-1-propanol
• NSC-8971
• NSC-170951
• (1R,2S)-1-phenyl-1-hydroxy-2-methylaminopropane
• 1-Hydroxy-2-methylamino-1-phenylpropane
• 1-Phenyl-1-hydroxy-2-methylaminopropane
• alpha-Hydroxy-beta-methylaminopropylbenzene
• NCI-C55652
• 1-alpha-(1-Methylaminoethyl)benzyl alcohol
• alpha-(1-(Methylamino)ethyl)benzenemethanol
• alpha-Hydroxy-beta-methyl amine propylbenzene
• DTXSID0022985
• (1R,2S)-2-methylamino-1-phenylpropan-1-ol
• Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (R-(R*,S*))-
• EC 206-080-5
• (1R,2S)-2-(methylamino)-1-phenyl-propan-1-ol
• Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (-)-
• EPHEDRINE (MART.)
• EPHEDRINE [MART.]
• Cenafed
• Decofed
• Genaphed
• Maxenal
• Myfedrine
• Robidrine
• Pseudo
• Pedia Care
• EPHEDRINE (EP MONOGRAPH)
• EPHEDRINE [EP MONOGRAPH]
• EPHEDRINE (USP MONOGRAPH)
• EPHEDRINE [USP MONOGRAPH]
• (-)-Ephedrine hemisulfate
• NSC8971
• Benzenemethanol, alpha-((1S)-1-(methylamino)ethyl)-, (alphaR)-
• Drixoral N.D.
• Benylin Decongestant
• Sudafed Decongestant
• Benzenemethanol, .alpha.-[(1S)-1-(methylamino)ethyl]-, (.alpha.R)-
• Efidac/24
• Pseudo-12
• (+-)-Ephedrine
• Pseudo 60's
• (-)-(1R,2S)-Ephedrine
• Eltor 120
• 1-EPHEDRINE
• C(O)(C(C)NC)c1ccccc1
• Ephedrine Erythro Isomer
• 649031_ALDRICH
• Erythro Isomer of Ephedrine
• Efedrina
• NSC170951
• 1(-)ephedrine
• EPHEDRINE [MI]
• EPHEDRINE [HSDB]
• EPHEDRINE [VANDF]
• DEA Code 8113
• D0LG8E
• (1R,2S)-2-methylamino-1-phenyl-propan-1-ol
• EPHEDRINE [WHO-DD]
• SCHEMBL4785
• Ephedrine [(-)-ephedrine]
• Lopac0_000501
• GTPL556
• (1r, 2s)-(-)-ephedrine
• CHEMBL211456
• DTXCID402985
• -(1R,2S)-(-)-ephedrine
• HY-B1195
• PDSP2_001327
• PDSP2_001330
• (1R,2S)-(-)-Ephedrine, 98%
• AKOS016011257
• Emerphed (ephedrine sulfate injection)
• EPHEDRINE, ANHYDROUS [WHO-IP]
• CCG-204592
• CS-4802
• DB01364
• NCGC00162174-01
• NCGC00162174-02
• LS-63964
• SBI-0051362.P003
• EPHEDRINUM, ANHYDROUS [WHO-IP LATIN]
• (1R,2S)-2-Methylamino-1-phenyl-1-propanol
• C01575
• D00124
• (1R*,2S*)-2-methylamino-1-phenyl-1-propanol
• (1R,2S)-2-(methylamino)-1-phenyl-1-propanol
• AB00375843_06
• A820118
• Q219626
• SR-01000075166
• (1R,2S)-(-)-2-Methylamino-1-phenyl-1-propanol
• J-500280
• SR-01000075166-1
• (1R,2S)-(-)-2-(N-methylamino)-1-phenylpropan-1-ol
• (1R,2S)-(-)-alpha-(1-Methylaminoethyl)benzenemethanol
• (R-(R*,S*))-alpha-(1-(Methylamino)ethyl)benzenemethanol
• (alpha R)-alpha-[(1S)-1-(Methylamino)ethyl]benzenemethanol
• Bencenometanol, Alfa-[(1S)-1-(metilamino) etil]-, (Alfa R)-
• PSEUDOEPHEDRINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]
• Benzenemethanol, .alpha.-[1-(methylamino)ethyl]-,[R-(R*,S*)]-
• BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (R-(R*,S*))-
• (R-(R*,S*))-.ALPHA.-(1-(METHYLAMINO)ETHYL)BENZENEMETHANOL [WHO-IP]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9845	98.45%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Lysosomes	0.5451	54.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9566	95.66%
OATP1B3 inhibitior	+	0.9659	96.59%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9237	92.37%
P-glycoprotein inhibitior	-	0.9741	97.41%
P-glycoprotein substrate	-	0.9308	93.08%
CYP3A4 substrate	-	0.7817	78.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6099	60.99%
CYP3A4 inhibition	-	0.9431	94.31%
CYP2C9 inhibition	-	0.7209	72.09%
CYP2C19 inhibition	-	0.5737	57.37%
CYP2D6 inhibition	+	0.5846	58.46%
CYP1A2 inhibition	-	0.5595	55.95%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.9070	90.70%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6242	62.42%
Carcinogenicity (trinary)	Non-required	0.7401	74.01%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9696	96.96%
Skin irritation	-	0.5871	58.71%
Skin corrosion	-	0.5499	54.99%
Ames mutagenesis	-	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7640	76.40%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.6651	66.51%
skin sensitisation	-	0.7718	77.18%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6496	64.96%
Acute Oral Toxicity (c)	III	0.8940	89.40%
Estrogen receptor binding	-	0.9205	92.05%
Androgen receptor binding	-	0.8448	84.48%
Thyroid receptor binding	-	0.8826	88.26%
Glucocorticoid receptor binding	-	0.9120	91.20%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	-	0.9004	90.04%
Honey bee toxicity	-	0.9411	94.11%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	-	0.8469	84.69%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	398.1 nM	Potency	via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	631 nM	Potency	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	125.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.30%	90.17%
CHEMBL2581	P07339	Cathepsin D	92.40%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.30%	95.56%
CHEMBL4208	P20618	Proteasome component C5	85.66%	90.00%
CHEMBL3902	P09211	Glutathione S-transferase Pi	85.00%	93.81%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.58%	85.14%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.03%	94.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.32%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.94%	94.62%
CHEMBL2535	P11166	Glucose transporter	82.59%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	81.47%	94.73%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	80.16%	89.23%

Plants that contains it

• Carapichea ipecacuanha
• Ephedra distachya
• Ephedra distachya subsp. helvetica
• Ephedra equisetina
• Ephedra fragilis
• Ephedra intermedia
• Ephedra przewalskii
• Ephedra sinica
• Festuca pratensis
• Hamelia patens
• Pinellia ternata
• Sophora flavescens
• Thymus quinquecostatus
• Thymus vulgaris

Cross-Links

• PubChem: 9294
• NPASS: NPC226778
• LOTUS: LTS0276367
• wikiData: Q219626