4-(2-aminopropyl)phenol

ID: ALA1546

Chembl Id: CHEMBL1546

Cas Number: 103-86-6

PubChem CID: 3651

Max Phase: Approved

First Approval: 1969

Molecular Formula: C9H13NO

Molecular Weight: 151.21

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dl-4-hydroxyamphetamine | Dl-p-hydroxyamphetamine | Norveritol | P-hydroxyamphetamine | Phenol, p-(2-aminopropyl)- | Pulsoton | Racemic p-hydroxyamphetamine | NSC-170995 | 4-(2-Aminopropyl)phenol|hydroxyamphetamine|103-86-6|Hydroxyamfetamine|4-Hydroxyamphetamine|Norveritol|Paredrine|Pulsoton|p-HYDROXYAMPHETAMINE|Norpholedrine|Oxamphetamine|Oksamfetamin|Oxamfetamin|Oxamphetaminium|Paredrinex|Nov-Pholedrin|Phenol, 4-(2-aminopropyl)-|Paradrine|Pedrolon|Phenol,4-(2-aminopropyl)-|Phenol, p-(2-aminoprShow More⌵

Synonyms from Alternative Forms(9): Hyroxyamfetamine hydrobromide | Hydroxyamfetamine hbr | Hydroxyamfetamine hydrobromide | Hydroxyamphetamine hbr | Hydroxyamphetamine hydrobromide | Oxamphetamine hydrobromide | Phenol, 4-(2-aminopropyl)-, hbr | NSC-61065 | Paredrine

Canonical SMILES:  CC(N)Cc1ccc(O)cc1

Standard InChI:  InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3

Standard InChI Key:  GIKNHHRFLCDOEU-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1546

   HYDROXYAMPHETAMINE

2. Alternative Forms:

   

   ALA1546

   Hydroxyamphetamine hydrobromide

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: No

Chirality: No

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 151.21

Molecular Weight (Monoisotopic): 151.0997

AlogP: 1.28

#Rotatable Bonds: 2

Polar Surface Area: 46.25

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.48

CX Basic pKa: 9.80

CX LogP: 1.00

CX LogD: -0.97

Aromatic Rings: 1

Heavy Atoms: 11

QED Weighted: 0.67

Np Likeness Score: 0.58

References

1. Kuglstatter A, Stahl M, Peters JU, Huber W, Stihle M, Schlatter D, Benz J, Ruf A, Roth D, Enderle T, Hennig M..  (2008)  Tyramine fragment binding to BACE-1.,  18  (4): [PMID:18226904] [10.1016/j.bmcl.2008.01.032]

2. Lewin AH, Miller GM, Gilmour B..  (2011)  Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class.,  19  (23): [PMID:22037049] [10.1016/j.bmc.2011.10.007]

3. Rice KC, Shiotani S, Creveling CR, Jacobson AE, Klee WA..  (1977)  N-(2,4,5-Trihydroxyphenehtyl)normetazocine, a potential irreversible inhibitor of the narcotic receptor.,  20  (5): [PMID:16133] [10.1021/jm00215a011]

4. Glennon RA..  (2017)  The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.,  60  (7): [PMID:28244748] [10.1021/acs.jmedchem.7b00085]

5. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

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

7. 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]

8. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(4):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6