Ephedrine

pseudoephedrine

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ephedrine

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Ephedrine

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Pseudoephedrine

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Phenylpropanolmethylamine

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(1R,2S)-2-(Methylamino)-1-phenylpropan-1-ol

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(1S,2S)-2-(Methylamino)-1-phenylpropan-1-ol

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Pseudoephedrine

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Ephedrine

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Éphédrine

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Ephedrine

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Ephedrine

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Pseudoephedrine

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Ephedrine

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SMILES:CNC(C)C(O)C1=CC=CC=C1

InChI:InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3

InChI key:KWGRBVOPPLSCSI-UHFFFAOYSA-N

Synonyms:

Fedrin,Ephoxamin,d-Pseudoephedrine base,SR-01000075166-1,Ephedrol,SBI-0051498.P003,(1S,2S)-2-(Methylamino)-1-phenylpropan-1-ol, D-psi-2-Methylamino-1-phenyl-1-propanol,Balminil Decongestant Syrup,ephedrine-(racemic), Ephedremal,PDSP1_001347,Lopac0_000501, Ephendronal,AKOS016011257,1(-)ephedrine,Spectrum3_001771,BSPBio_003261,(1s, 2s) pseudoephedrine,HSDB 3177,299-42-3,PSEUDOEPHEDRINE [WHO-DD],DTXSID0023537,PSEUDOEPHEDRINE [MART.],Emerphed (ephedrine sulfate injection),(-)-alpha-(1-Methylaminoethyl)benzyl alcohol,CHEMBL1590,PSEUDOEPHEDRINE HYDROCHLORIDE IMPURITY A [EP IMPURITY],Ephedrine, L-(-)-, Pseudoefedrina [INN-Spanish],(I)-Ephedrin, Ephedrine [USAN:BAN], Zephrol, (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol,Ephedrine l-form,A820118,Acunaso (TN),BIDD:GT0817,(+) threo-2-(methylamino)-1-phenyl-1-propanol,(1S,2S)-(+)-Pseudoephedrine,Acunaso,CCG-204592,(1S,2S)-2-(methylamino)-1-phenyl-propan-1-ol, Ephedrine l-form,PDSP2_001327,7CUC9DDI9F, Efidac 24 PseudoephedrineHcl,Ephedrine (USP), Sudafed (TN),CHEBI:51209,EC 202-018-6,Ephedrine (TN), Eciphin,DEA Code 8113,BRD-K84175871-003-02-2,Ephedrin,KBio2_003926, Triaminic Infant Oral Decongestant Drops,I-Sedrin,299E423,(1R,2S)-2-Methylamino-1-phenyl-1-propanol, Alpha-(1-(Methylamino)ethyl)benzyl alcohol,NSC-170951,Ephedrital,AB00375843_06, (1S,2S)-(+)-Pseudoephedrine, L(-)-Ephedrine,Zephrol,NCGC00162174-01,1-Phenyl-1-hydroxy-2-methylaminopropane,Pseudoephedrine, Pseudoephedrine [INN:BAN],DB01364, Nasol, Triaminic AM Decongestant Formula,Efedrin,CS-4802,UNII-7CUC9DDI9F,Isoephedrine,Kratedyn,(1R,2S)-2-(methylamino)-1-phenylpropan-1-ol,C01575,GTPL556,trans-Ephedrine,SPBio_001365,alpha-[1-(Methylamino)ethyl]-benzenemethanol,Biophedrin,EINECS 206-080-5,(1S,2S) pseudoephedrine, (1R,2R)-Ephedrine,Pseudoephedrine (INN),(L)-EPHEDRINE,alpha-Hydroxy-beta-methylaminopropylbenzene,BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (S-(R*,R*))-,(-)-(1R,2S)-Ephedrine,(1S,2S)-2-(Methylamino)-1-phenyl-1-propanol,Neodurasina,l-alpha-(1-Methylaminoethyl)benzyl alcohol,Pseudoephedrinum [INN-Latin], CPDD 0049,Sal-Phedrine,(1S,2S)-(+)-Pseudoephedrine, 98%,L(+)-psi-Ephedrine,1-Sedrin, L-(+)-Ephedrine,PDSP2_001330,Ephedrine [USAN:BAN],Ephedsol, Sudafed Decongestant 12 Hour,Psi-ephedrin,EPHEDRINE [USP MONOGRAPH], Sanedrine,EPHEDRINUM, ANHYDROUS [WHO-IP LATIN], Efedrin,(1R,2S)-(-)-alpha-(1-Methylaminoethyl)benzenemethanol,EPHEDRINE [VANDF],Benzenemethanol, alpha-((1S)-1-(methylamino)ethyl)-, (alphaS)-,(1R,2S)-(-)-Ephedrine, 98%,NSC170951, Benzenemethanol, alpha-((1S)-1-(methylamino)ethyl)-, (alpha-S)-(9CI),IDI1_000451,Benzenemethanol, alpha-((1S)-1-(methylamino)ethyl)-, (alpha-S)-,2-Methylamino-1-phenyl-1-propanol, Pseudoephedrine (INN),EPHEDRINE [MART.], L-Ephedrine,Benzenemethanol, .alpha.-[(1S)-1-(methylamino)ethyl]-, (.alpha.R)-,Neodurasina (TN),(1R*,2S*)-2-methylamino-1-phenyl-1-propanol,Pseudoephedrine d-form, Dimetapp Decongestant Pediatric Drops,SBI-0051362.P003,d-psi-Ephedrine,DivK1c_000451,EPHEDRINE HYDROCHLORIDE IMPURITY B [EP IMPURITY], Ephedrital,1-(S),2-(R)-ERYTHRO-(+)-EPHEDRINE,SR-01000075166,1-alpha-(1-Methylaminoethyl)benzyl alcohol,Vencipon,Spectrum2_001303,Sudafed, Mandrin, Pseudoephedrine Ephedrine,AKOS025401512,L-(+)-Pseudoephedrine,(1s, 2s)-(+)-pseudoephedrine,Pseudoephedrinum,(1R,2S)-2-(methylamino)-1-phenyl-1-propanol,CHEBI:15407,(+) pseudoephedrine, (1S,2S)-Pseudoephedrine, polymer-bound,Ephedrine, anhydrous,(+)-psi-Ephedrine,Ephedrinum, anhydrous,(1R,2S)-2-methylamino-1-phenylpropan-1-ol,EPHEDRINE [MI],Pseudoephedrine Ephedrine, Sudafed Decongestant Extra Strength,KBioGR_001763,Nasol,(-)-Ephedrine,SCHEMBL4785,Spectrum_000878,PSEUDOEPHEDRINE [MI],(1R,2S)-(-)-2-(N-methylamino)-1-phenylpropan-1-ol,Benzenemethanol, alpha-((1S)-1-(methylamino)ethyl)-, (alphaR)-,Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (R-(R*,S*))-,d-Isoephedrine,(1R,2S)-2-(Methylamino)-1-phenylpropan-1-ol,Ephedral,NCGC00178180-01, Ephedsol,(R,S)-2-(Methylamino)-1-phenylpropan-1-ol, (1S,2S)-2-Methylamino-1-phenyl-1-propanol,(1S,2S)-2-methylamino-1-phenylpropan-1-ol, Ephedrine (USP),(.ALPHA.S)-.ALPHA.-((1R)-1-(METHYLAMINO)ETHYL)BENZENEMETHANOL,HSDB 3072,(+)-(1S,2S)-Pseudoephedrine, Ephedral,AI3-02761,(1R,2S)-(-)-2-Methylamino-1-phenyl-1-propanol,ZINC20259,Pseudoefedrina [INN-Spanish],(1R,2S)-1-phenyl-1-hydroxy-2-methylaminopropane,(1R,2S)-2-(methylamino)-1-phenyl-propan-1-ol, Pseudoephedrinum [INN-Latin], Ephedrosan,Isoephedrine, d-,Xenadrine, Fedrin,ZINC74836,PSEUDOEPHEDRINE [VANDF],(R-(R*,S*))-.ALPHA.-(1-(METHYLAMINO)ETHYL)BENZENEMETHANOL [WHO-IP], 1-EPHEDRINE,d-Pseudoephedrine,KBio3_002762,KBioSS_001358,J-500280, (+)-(1S,2S)-Pseudoephedrine, Dimetapp Decongestant,GTPL7286,Lopac-E-3250,EC 206-080-5,Manadrin,(-)-Ephedrine hemisulfate,(1S,2S)-2-Methylamino-1-phenylpropan-1-ol, (1S,2R)-Ephedrine,l-2-Methylamino-1-phenylpropanol,1-2-Methylamino-1-phenylpropanol,pseudophedrine sulphate,90-82-4,(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol,psi-Ephedrine, (+)-,l-Ephedrine,Sanedrine,Pseudoephedrine [INN:BAN],C02765,UNII-GN83C131XS,Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (S-(R*,R*))-,NCI-C55652,Pseudoefedrina,(S,S)-(+)-Pseudoephedrine solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material,(1S,2S)-Ephedrine,alpha-(1-(Methylamino)ethyl)benzenemethanol,HY-B1195, (+)-Ephedrin,Ephedrotal,alpha-Hydroxy-beta-methyl amine propylbenzene, Lexofedrin,PSEUDOEPHEDRINE,Mandrin,2-(Methylamino)-1-phenyl-1-propanol,DTXSID0022985,L(-)-Ephedrine,racephedrine,(1S,2S)-Pseudoephedrine,Ephendronal,PSEUDOEPHEDRINE [INN], Kratedyn,Besan, Ephedrine (TN),EPHEDRINE [WHO-DD],NCI60_002955,064P256,KBio1_000451,Pseudoephedrine, (+)-,PSEUDOEPHEDRINE [HSDB],Ephedrine,EPHEDRINE [HSDB],NSC 170951,DB00852,Pseudoephedrine (D),NCGC00162174-02,NSC 8971,NINDS_000451,KBio2_006494, (L)-EPHEDRINE,Eciphin, Pseudoephedrine d-form,1-Hydroxy-2-methylamino-1-phenylpropane,SCHEMBL4368, Ephedrotal,Pseudoephedrine polistirex, Vencipon,Spectrum5_000650,Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (-)-,BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (R-(R*,S*))-, Manadrin,alpha-(1-(Methylamino)ethyl)benzyl alcohol,Benzenemethanol, .alpha.-[(1S)-1-(methylamino)ethyl]-, (.alpha.S)-, L-(-)-Ephedrine,EPHEDRINE, ANHYDROUS [WHO-IP], (1S,2S)-Pseudoephedrine,NSC-8971, 1-Sedrin, Ephedrol,Ephedrosan,(1R,2S)-2-Methylamino-1-phenylpropan-1-ol,Pseudoephedrine, L-(+)-,Phenylpropanolmethylamine,D08449,EPHEDRINE [EP MONOGRAPH],CHEMBL211456,(+)-Pseudoephedrine,Spectrum4_001162,d-psi-2-Methylamino-1-phenyl-1-propanol,NCGC00015408-01,1-Phenyl-2-methylaminopropanol,Q219626,Q263958, Ephedrin,Lexofedrin,(+)-threo-Ephedrine,l-Erythro-2-(methylamino)-1-phenylpropan-1-ol,KBio2_001358,Norephedrine, N-methyl-,GN83C131XS, Drixoral Nasal Decongestant,Ephedremal,(1r, 2s)-(-)-ephedrine,EINECS 202-018-6, D-Ephedrine, Ephoxamin,D00124, I-Sedrin, Racephedrine,Psi-ephedrine,BENZENEMETHANOL, .ALPHA.-((1S)-1-(METHYLAMINO)ETHYL)-, (.ALPHA.S)-

Categories (non-exhaustive):

Substituted piperazine Substituted phenylmorpholine Substituted cathinone Methylphenidate analogue Aminorex analogue Imidazopyridine DOx Benzimidazole opioid Arylcyclohexylamine Xanthine Tryptamine Tropane Tricyclic Thiobarbiturate Cyclopyrrolone Pyrazolopyrimidine Substituted phenethylamine Lysergamide Diphenylbutylpiperidine Racetam Benzodiazepine Barbiturate Alkyl nitrite 25nb 2c Substituted amphetamine Naphthoylindole Phenylacetylindole Benzoylindole Cyclohexylphenol Check naphthoylpyrrole Naphthylmethylindene Tetramethylcyclopropanoylindoles Adamantoylindoles Indole3carboxylate ester Indazole3carboxamide Morphinan

Similarities

Being able to identify molecules that are similar to the one we study can allow to infer some of its properties. There are several ways of measuring the similarity between molecules, by their structure, effects, pharmacological interactions etc. In the following, you can find similar molecules according to various criterions and tools that we developed. To understand the limitations of these comparisons, it is crucial to always refer to the methodology that was used to measure those similarities. Please note: This information is provided solely for informational purposes and should not be interpreted as medical advice.

Similarity type

To measure structural similarity, we use the Mol2vec method, which is a neural network that processes molecules and transform them into points in spaces, such that molecules with chemically related substructures are transformed into points that are close in space.

Legal statuses

For each country, we look for references and regulations related to this molecule, of to families of compounds that this molecule belongs to.

Disclaimer: The information provided on this website regarding the legal references of molecules is for informational purposes only and does not constitute legal advice. While we strive to keep the information up-to-date and accurate, laws and regulations may change over time. Therefore, we cannot guarantee the completeness, accuracy, or applicability of the information provided. It is important to always refer to the original legal texts and consult with a qualified legal professional before making any decisions based on the information provided on this website.

Always double check the sources provided, there can be classification errors. Our system may also have missed certain references. : This molecule was added in the legislation: This molecule was removed from the legislation

Country:

Type of legislation

Narcotics

2021-05-23

Molecule mentionned as "phénéthylamines et des alpha-méthylphénéthylamines"

Psychotropes

The system hasn't detected any mention of this drug in France as a Psychotropes but you should always double check by yourself.

Molecule properties

Using the KGPT Deep Learning model, we predict several property of the molecule. Predictions are grouped by the dataset that was used to get those prediction. Along with each prediction, we provide a plot that shows the distribution of predicted values on the train/test/val dataset. This gives an estimate of the reliability of the model.

Description: A dataset focused on predicting the inhibitory effects of molecules on the enzyme beta-secretase 1 (BACE1). BACE1 inhibition is a potential target for Alzheimer's disease treatment.

Class

TrainValTest

2.88-3.70-1.36

Description: A dataset providing insights on the ability of molecules to penetrate the blood-brain barrier. Crucial for understanding the potential of molecules as central nervous system drugs.

p_np

TrainValTest

-2.24-3.290.40

Description: This dataset deals with the FDA approval status and clinical trial toxicity of molecules. Important for understanding the safety and regulatory status of compounds.

CT_TOX

TrainValTest

-0.49-0.78-0.91

FDA_APPROVED

TrainValTest

0.53-1.27-0.50

Description: A dataset that predicts the solubility of molecules in water. Solubility is an essential property influencing bioavailability and the potential formulation of a drug.

logSolubilitylog(mol/L)

1.10

TrainValTest

Description: This dataset is centered on predicting the free energy when a molecule is dissolved in water. The energy changes can affect molecular interactions in biological systems.

freesolvkcal/mol

-2.20

TrainValTest

Description: A dataset predicting the lipophilicity of molecules. Lipophilicity is a crucial factor affecting the distribution, metabolism, and excretion of drugs in the body.

lipoAlogP

-2.26

TrainValTest

Description: This dataset gives insights into the metabolic stability of molecules. High metabolic stability often results in a longer half-life, influencing drug dosage and frequency.

low

TrainValTest

-0.17-3.50-2.88

high

TrainValTest

0.72-3.55-0.49

27 entries

12 entries

617 entries

Affinities

Binding affinities with a list of 61 predefined docking sites. Those affinities are used to compute the interactions similarities.

Interaction of this molecule with metabolism

We use a Deep Learning model to predict the interactions of this molecule with metabolism. Refer to the source to understand the methodology.

Reactions that metabolize this molecule

Alkyl-OH-glucuronidation BTMR0165

Enzymes: 2.4.1.17

Reagents

Metabolite: InChI=1S/C16H23...

Sulfation of secondary alcohol BTMR0502

Enzymes: 2.8.2.2

Reagents

Metabolite: InChI=1S/C10H15...

O-Hydroxylation of monosubstituted benzene BTMR1034

Enzymes: CYP1A2 CYP2C8 CYP2C9 CYP2C19 CYP3A4

Reagents

2-[1-Hydroxy-2-(methylamino)propyl]phenol

Oxidation of secondary alcohol to ketone BTMR0079

Enzymes: CYP1A2 CYP2C9 CYP2C19

Reagents

Methcathinone

Hydroxylation of benzene on carbon para to electron donating group BTMR1047

Enzymes: CYP1A2 CYP2C8 CYP2C9 CYP2D6 CYP3A4

Reagents

Oxilofrine

Hydroxylation of terminal methyl BTMR1061

Enzymes: CYP1A2 CYP2A6 CYP2B6 CYP2C8 CYP2C9 CYP2C19 CYP2D6 CYP2E1 CYP3A4

Reagents

Metabolite: InChI=1S/C10H15...

Terminal desaturation BTMR1190

Enzymes: CYP1A2 CYP2A6 CYP2C9 CYP2D6 CYP3A4

Reagents

InChI=1S/C10H13NO/c1...

N-Dealkylation of acyclic secondary amine BTMR1140

Enzymes: CYP1A2 CYP2B6 CYP2C8 CYP2C9 CYP2C19 CYP2D6 CYP3A4

Reagents

Phenylacetylcarbinol

N-Dealkylation of acyclic secondary amine BTMR1140

Enzymes: CYP1A2 CYP2B6 CYP2C8 CYP2C9 CYP2C19 CYP2D6 CYP3A4

Reagents

Methylamine

[14C]methylamine

N-Dealkylation of acyclic secondary amine BTMR1140

Enzymes: CYP1A2 CYP2B6 CYP2C8 CYP2C9 CYP2C19 CYP2D6 CYP3A4

Reagents

Phenylpropanolamine

Norephedrine

Cathine

(-)-Norephedrine

Norephedrine

(1S)-2-amino-1-phenylpropan-1-ol

Phenylpropanolamine

L-Norpseudoephedrine

Cathine

Phenylpropanolamine

Reactions that metabolism produce from this molecule

N-Dealkylation of acyclic tertiary amine BTMR1142

Enzymes: CYP1A2 CYP2A6 CYP2B6 CYP2C8 CYP2C9 CYP2C19 CYP2D6 CYP2E1 CYP3A4

Products

Methylephedrine

N-Methylpseudoephedrine

N-Methylephedrine

N-Dealkylation of acyclic tertiary amine BTMR1142

Enzymes: CYP1A2 CYP2A6 CYP2B6 CYP2C8 CYP2C9 CYP2C19 CYP2D6 CYP2E1 CYP3A4

Products

Etafedrine

Hydrolysis of carboxylic acid ester BTMR0143

Enzymes: 3.1.1.1

Products

O-Acetylephedrine

O-Acetylpseudoephedrine

3'-Dehydroxylation of substituted benzene BTMR1314

Enzymes: Unspecified bacterial dehydroxylase

Products

m-Hydroxyephedrine

N-Dealkylation of acyclic tertiary amine BTMR1142

Enzymes: CYP1A2 CYP2A6 CYP2B6 CYP2C8 CYP2C9 CYP2C19 CYP2D6 CYP2E1 CYP3A4

Products

Cinnamedrine

4'-Dehydroxylation of substituted benzene BTMR1012

Enzymes: Unspecified bacterial dehydroxylase

Products

Oxilofrine

Reduction of carbonyl BTMR0368

Enzymes: 1.1.1.184

Products

Methcathinone

Hydroxylation of non-terminal aliphatic carbon adjacent to aromatic ring BTMR1077

Enzymes: CYP1A2 CYP2C8 CYP2C9 CYP2D6 CYP3A4

Products

Ephedrine

pseudoephedrine

ephedrine

Ephedrine

Pseudoephedrine

Phenylpropanolmethylamine

(1R,2S)-2-(Methylamino)-1-phenylpropan-1-ol

(1S,2S)-2-(Methylamino)-1-phenylpropan-1-ol

Pseudoephedrine

Ephedrine

Éphédrine

Ephedrine

Ephedrine

Pseudoephedrine

Ephedrine

Similarities

Legal statuses

Molecule properties

Advanced insights

Affinities

Interaction of this molecule with metabolism

Metabolite: InChI=1S/C16H23...

Metabolite: InChI=1S/C10H15...

2-[1-Hydroxy-2-(methylamino)propyl]phenol

Methcathinone

Methcathinone

Methcathinone

Oxilofrine

Oxilofrine

Oxilofrine

Metabolite: InChI=1S/C10H15...

InChI=1S/C10H13NO/c1...

Phenylacetylcarbinol

Methylamine

Methylamine

[14C]methylamine

Phenylpropanolamine

Norephedrine

Cathine

(-)-Norephedrine

Norephedrine

(1S)-2-amino-1-phenylpropan-1-ol

Phenylpropanolamine

Phenylpropanolamine

L-Norpseudoephedrine

Cathine

Phenylpropanolamine

Methylephedrine

N-Methylpseudoephedrine

N-Methylpseudoephedrine

N-Methylephedrine

Etafedrine

Etafedrine

O-Acetylephedrine

O-Acetylpseudoephedrine

m-Hydroxyephedrine

Cinnamedrine

Oxilofrine

Oxilofrine

Oxilofrine

Methcathinone

Methcathinone

Methcathinone

Methamphetamine

methamphetamine

MA

Methamphetamine

Méthamphétamine

Methamphetamine

Methamphetamine

Levomethamphetamine