(3S,8R)-8-Methyl-3-phenyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester

ID: ALA1790051

Chembl Id: CHEMBL1790051

PubChem CID: 56681668

Max Phase: Preclinical

Molecular Formula: C16H22ClNO2

Molecular Weight: 259.35

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: WIN-35065-2 | CHEMBL1790051|WIN-35065-2

Canonical SMILES:  COC(=O)[C@@H]1C2CC[C@H](C[C@@H]1c1ccccc1)N2C.Cl

Standard InChI:  InChI=1S/C16H21NO2.ClH/c1-17-12-8-9-14(17)15(16(18)19-2)13(10-12)11-6-4-3-5-7-11;/h3-7,12-15H,8-10H2,1-2H3;1H/t12-,13-,14?,15+;/m1./s1

Standard InChI Key:  LTKIILYBJZQLLW-QNIIYNMLSA-N

Associated Targets(Human)

SLC6A3 Tclin Dopamine transporter (10535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A4 Tclin Monoamine transporters; serotonin & dopamine (417 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A4 Tclin Serotonin transporter (12625 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Slc6a3 Dopamine transporter (6071 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc6a2 Norepinephrine transporter (2222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc6a4 Serotonin transporter (6087 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc6a3 Monoamine transporters; Norepininephrine & dopamine (561 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc6a4 Monoamine transporters; serotonin & dopamine (1148 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A3 Dopamine transporter (17 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bos taurus (956 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Gabrp GABA-A receptor; anion channel (5731 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: 259.35Molecular Weight (Monoisotopic): 259.1572AlogP: 2.43#Rotatable Bonds: 2
Polar Surface Area: 29.54Molecular Species: BASEHBA: 3HBD:
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 9.27CX LogP: 2.51CX LogD: 0.64
Aromatic Rings: 1Heavy Atoms: 19QED Weighted: 0.76Np Likeness Score: 0.65

References

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21. Jiang S, Chang AC, Abraham P, Kuhar MJ, Carroll FI..  (1998)  Synthesis and transporter binding properties of (R)-2 beta, 3 beta- and (R)-2 alpha, 3 alpha-diaryltropanes.,  (24): [PMID:9934496] [10.1016/s0960-894x(98)00673-8]
22. Blough BE, Abraham P, Mills AC, Lewin AH, Boja JW, Scheffel U, Kuhar MJ, Carroll FI..  (1997)  3 Beta-(4-ethyl-3-iodophenyl)nortropane-2 beta-carboxylic acid methyl ester as a high-affinity selective ligand for the serotonin transporter.,  40  (24): [PMID:9397165] [10.1021/jm970492z]
23. Kelkar SV, Izenwasser S, Katz JL, Klein CL, Zhu N, Trudell ML..  (1994)  Synthesis, cocaine receptor affinity, and dopamine uptake inhibition of several new 2 beta-substituted 3 beta-phenyltropanes.,  37  (23): [PMID:7966147] [10.1021/jm00049a004]
24. Carroll FI, Kotian P, Dehghani A, Gray JL, Kuzemko MA, Parham KA, Abraham P, Lewin AH, Boja JW, Kuhar MJ..  (1995)  Cocaine and 3 beta-(4'-substituted phenyl)tropane-2 beta-carboxylic acid ester and amide analogues. New high-affinity and selective compounds for the dopamine transporter.,  38  (2): [PMID:7830281] [10.1021/jm00002a020]
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26. Holmquist CR, Keverline-Frantz KI, Abraham P, Boja JW, Kuhar MJ, Carroll FI..  (1996)  3 alpha-(4'-substituted phenyl)tropane-2 beta-carboxylic acid methyl esters: novel ligands with high affinity and selectivity at the dopamine transporter.,  39  (21): [PMID:8863789] [10.1021/jm960515u]
27. Holmquist CR, Keverline-Frantz KI, Abraham P, Boja JW, Kuhar MJ, Carroll FI..  (1996)  3 alpha-(4'-substituted phenyl)tropane-2 beta-carboxylic acid methyl esters: novel ligands with high affinity and selectivity at the dopamine transporter.,  39  (21): [PMID:8863789] [10.1021/jm960515u]
28. Lomenzo SA, Izenwasser S, Katz JL, Terry PD, Zhu N, Klein CL, Trudell ML..  (1997)  Synthesis, structure, dopamine transporter affinity, and dopamine uptake inhibition of 6-alkyl-3-benzyl-2-[(methoxycarbonyl)methyl]tropane derivatives.,  40  (26): [PMID:9435910] [10.1021/jm970549h]
29. Chen Z, Izenwasser S, Katz JL, Zhu N, Klein CL, Trudell ML..  (1996)  Synthesis and dopamine transporter affinity of 2-(methoxycarbonyl)-9-methyl-3-phenyl-9-azabicyclo[3.3.1]nonane derivatives.,  39  (24): [PMID:8941387] [10.1021/jm960507d]
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34. Carroll FI, Lewin AH, Boja JW, Kuhar MJ..  (1992)  Cocaine receptor: biochemical characterization and structure-activity relationships of cocaine analogues at the dopamine transporter.,  35  (6): [PMID:1552510] [10.1021/jm00084a001]
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36. Carroll FI, Lewin AH, Boja JW, Kuhar MJ..  (1992)  Cocaine receptor: biochemical characterization and structure-activity relationships of cocaine analogues at the dopamine transporter.,  35  (6): [PMID:1552510] [10.1021/jm00084a001]
37. Carroll FI, Lewin AH, Boja JW, Kuhar MJ..  (1992)  Cocaine receptor: biochemical characterization and structure-activity relationships of cocaine analogues at the dopamine transporter.,  35  (6): [PMID:1552510] [10.1021/jm00084a001]
38. Carroll FI, Blough BE, Nie Z, Kuhar MJ, Howell LL, Navarro HA..  (2005)  Synthesis and monoamine transporter binding properties of 3beta-(3',4'-disubstituted phenyl)tropane-2beta-carboxylic acid methyl esters.,  48  (8): [PMID:15828814] [10.1021/jm040185a]
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