1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic acid amide

ID: ALA60724

Chembl Id: CHEMBL60724

Cas Number: 112794-29-3

PubChem CID: 4962026

Max Phase: Preclinical

Molecular Formula: C10H12N2O

Molecular Weight: 176.22

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  NC(=O)C1Cc2ccccc2CN1

Standard InChI:  InChI=1S/C10H12N2O/c11-10(13)9-5-7-3-1-2-4-8(7)6-12-9/h1-4,9,12H,5-6H2,(H2,11,13)

Standard InChI Key:  JFMNKDRNEZZRBW-UHFFFAOYSA-N

Alternative Forms

Associated Targets(Human)

PNMT Tchem Phenylethanolamine N-methyltransferase (540 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

PNMT Phenylethanolamine N-methyltransferase (752 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra2c Adrenergic receptor alpha-2 (3313 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra2a Alpha-2a adrenergic receptor (204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 176.22Molecular Weight (Monoisotopic): 176.0950AlogP: 0.19#Rotatable Bonds: 1
Polar Surface Area: 55.12Molecular Species: NEUTRALHBA: 2HBD: 2
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 7.56CX LogP: 0.45CX LogD: 0.07
Aromatic Rings: 1Heavy Atoms: 13QED Weighted: 0.64Np Likeness Score: 0.15

References

1. Grunewald GL, Dahanukar VH, Teoh B, Criscione KR..  (1999)  3,7-Disubstituted-1,2,3,4-tetrahydroisoquinolines display remarkable potency and selectivity as inhibitors of phenylethanolamine N-methyltransferase versus the alpha2-adrenoceptor.,  42  (11): [PMID:10354406] [10.1021/jm9807252]
2. Grunewald GL, Sall DJ, Monn JA..  (1988)  Synthesis and evaluation of 3-substituted analogues of 1,2,3,4-tetrahydroisoquinoline as inhibitors of phenylethanolamine N-methyltransferase.,  31  (4): [PMID:3351861] [10.1021/jm00399a024]
3. Lu J,Bart AG,Wu Q,Criscione KR,McLeish MJ,Scott EE,Grunewald GL.  (2020)  Structure-Based Drug Design of Bisubstrate Inhibitors of Phenylethanolamine N-Methyltransferase Possessing Low Nanomolar Affinity at Both Substrate Binding Domains.,  63  (22): [PMID:33147410] [10.1021/acs.jmedchem.0c01475]

Source