D-161

D-161
Identifiers
  • 4-((((3S,6S)-6-Benzhydryltetrahydro-2H-pyran-3-yl)amino)methyl)phenol
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC25H27NO2
Molar mass373.496 g·mol−1
3D model (JSmol)
  • Oc2ccc(cc2)CNC(CC3)COC3C(c1ccccc1)c4ccccc4
  • InChI=1S/C25H27NO2/c27-23-14-11-19(12-15-23)17-26-22-13-16-24(28-18-22)25(20-7-3-1-4-8-20)21-9-5-2-6-10-21/h1-12,14-15,22,24-27H,13,16-18H2/t22-,24-/m0/s1
  • Key:CFCFEXCFOQWYQK-UPVQGACJSA-N
  (verify)

D-161 is a chemical known in research circles as a triple reuptake inhibitor. Although this compound has lent support to the inclusion of dopamine in the monoamine hypothesis of depression, D-161 has not been tested in clinical trials.

A more recent study was reported.

A couple of patents are also disclosed.

Synthesis

The synthesis of this agent has been reported.

References

  1. ↑ Dutta AK, Ghosh B, Biswas S, Reith ME (July 2008). "D-161, a novel pyran-based triple monoamine transporter blocker: behavioral pharmacological evidence for antidepressant-like action". European Journal of Pharmacology. 589 (1–3): 73–9. doi:10.1016/j.ejphar.2008.05.008. PMID 18561912.
  2. ↑ Sharma, H., Santra, S., Debnath, J., Antonio, T., Reith, M., Dutta, A. (January 2014). "Flexible and biomimetic analogs of triple uptake inhibitor 4-((((3S,6S)-6-benzhydryltetrahydro-2H-pyran-3-yl)amino)methyl)phenol: Synthesis, biological characterization, and development of a pharmacophore model". Bioorganic & Medicinal Chemistry. 22 (1): 311–324. doi:10.1016/j.bmc.2013.11.017. ISSN 0968-0896. PMC 3913050. Retrieved 6 December 2025.
  3. ↑ Aloke K. Dutta, WO2005105075 (Wayne State University).
  4. ↑ Aloke K. Dutta, US8017791 (2011 to Wayne State University).
  5. ↑ Zhang, S., Fernandez, F., Hazeldine, S., Deschamps, J., Zhen, J., Reith, M. E. A., Dutta, A. K. (1 July 2006). "Further Structural Exploration of Trisubstituted Asymmetric Pyran Derivatives (2 S ,4 R ,5 R )-2-Benzhydryl-5-benzylamino-tetrahydropyran-4-ol and Their Corresponding Disubstituted (3 S ,6 S ) Pyran Derivatives: A Proposed Pharmacophore Model for High-Affinity Interaction with the Dopamine, Serotonin, and Norepinephrine Transporters". Journal of Medicinal Chemistry. 49 (14): 4239–4247. doi:10.1021/jm0601699.
  6. ↑ Gopishetty, B., Hazeldine, S., Santra, S., Johnson, M., Modi, G., Ali, S., Zhen, J., Reith, M., Dutta, A. (28 April 2011). "Further Structure−Activity Relationship Studies on 4-((((3 S ,6 S )-6-Benzhydryltetrahydro-2 H -pyran-3-yl)amino)methyl)phenol: Identification of Compounds with Triple Uptake Inhibitory Activity as Potential Antidepressant Agents". Journal of Medicinal Chemistry. 54 (8): 2924–2932. doi:10.1021/jm200020a. PMC 3085959.