2-Methylamino-1-phenyl-propan-1-ol

ID: ALA211456

Cas Number: 299-42-3

PubChem CID: 9294

Product Number: R472385, Order Now?

Max Phase: Approved

First Approval: 2016

Molecular Formula: C10H15NO

Molecular Weight: 165.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (-)-ephedrine | Ephedrine | Ephedrine, anhydrous | Ephedrinum, anhydrous | L-ephedrine | Xenadrine | NSC-170951 | NSC-8971 | Ephedrine|l-Ephedrine|(-)-Ephedrine|299-42-3|Ephedrin|L(-)-Ephedrine|Lexofedrin|Ephedrol|Mandrin|Sanedrine|Fedrin|I-Sedrin|1-Sedrin|Ephedrine l-form|(1R,2S)-2-(methylamino)-1-phenylpropan-1-ol|Xenadrine|Norephedrine, N-methyl-|Ephedrine, anhydrous|Ephedrital|Ephedrosan|Ephedrotal|Ephedsol|Ephendronal|Ephoxamin|Kratedyn|Manadrin|Vencipon|Efedrin|Zephrol|Nasol|Ephedrine, L-(Show More⌵

Synonyms from Alternative Forms(32): (-)-Ephedrine Hemisulfate | Ephedrine Sulfate | Ephedrine sulphate | Ephedrini sulfas | Akovaz | Corphedra | Emerphed | Expansyl | Franol plus | Franol-plus | Ephedrine hydrochloride | (-)-ephedrine hydrochloride | Ephedrine hcl | Ephedrini hydrochloridum | L-ephedrine hydrochloride | NSC-759611 | Amesec | Asmapax | Bronchipax | C.a.m. | Do-do | Ephed hcl | Ephed in nor saline | Expurhin | Franol | Haymine | Rezipres | Secron | Tabasan | Taumasthman | Tedral | Tedral sa

Canonical SMILES:  CN[C@@H](C)[C@H](O)c1ccccc1

Standard 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

Standard InChI Key:  KWGRBVOPPLSCSI-WPRPVWTQSA-N

Molfile:  

     RDKit          2D

 12 12  0  0  1  0  0  0  0  0999 V2000
   -0.2708   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3500    0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208    0.1375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5500   -1.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    1.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7958    1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708    2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125    1.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  3  4  1  1
  1  5  1  1
  6  2  2  0
  7  2  1  0
  8  4  1  0
  9  3  1  0
 10  6  1  0
 11  7  2  0
 12 11  1  0
 10 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA211456

   EPHEDRINE

2. Alternative Forms:

   

   ALA211456

   EPHEDRINE HEMISULFATE
3. 

   ALA211456

   EPHEDRINE SULFATE
4. 

   ALA211456

   (1R,2S)-(−)-Ephedrine hydrochloride

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 165.24

Molecular Weight (Monoisotopic): 165.1154

AlogP: 1.33

#Rotatable Bonds: 3

Polar Surface Area: 32.26

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: 9.52

CX LogP: 1.32

CX LogD: -0.78

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.71

Np Likeness Score: 0.43

References

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3. Shimojima Y, Shirai T, Baba T, Hayashi H..  (1985)  1H-2-Benzopyran-1-one derivatives, microbial products with pharmacological activity. Conversion into orally active derivatives with antiinflammatory and antiulcer activities.,  28  (1): [PMID:3965711] [10.1021/jm00379a002]

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13. Settimo L, Bellman K, Knegtel RM..  (2013)  Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.,  [PMID:24249037] [10.1007/s11095-013-1232-z]

14. Settimo L, Bellman K, Knegtel RM..  (2013)  Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.,  [PMID:24249037] [10.1007/s11095-013-1232-z]

15. PubChem BioAssay data set, 

16. Hava M, Bernstein J, Smissman EE, El-Antably S..  (1976)  A conformational study of beta-phenethanolamine receptor sites. 8. Pharmacological study of 3-isopropylamino-2-phenyl-trans-2-decalols.,  19  (1): [PMID:1246053] [10.1021/jm00223a011]

17. Scherrer RA, Howard SM..  (1977)  Use of distribution coefficients in quantitative structure-activity relationships.,  20  (1): [PMID:13215] [10.1021/jm00211a010]

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19. Russo CM, Adhikari AA, Wallach DR, Fernandes S, Balch AN, Kerr WG, Chisholm JD..  (2015)  Synthesis and initial evaluation of quinoline-based inhibitors of the SH2-containing inositol 5'-phosphatase (SHIP).,  25  (22): [PMID:26453006] [10.1016/j.bmcl.2015.09.034]

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22. Chen M, Suzuki A, Thakkar S, Yu K, Hu C, Tong W..  (2016)  DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.,  21  (4): [PMID:26948801] [10.1016/j.drudis.2016.02.015]

23. Unpublished dataset, 

24. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

25. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

26. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

27. Unpublished dataset, 

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Source

Source(9):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• AstraZeneca Deposited Data
• Withdrawn Drugs
• WHO Anatomical Therapeutic Chemical Classification
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6