Chemistry:HP-505
From HandWiki
Short description: Chemical compound
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| Formula | C18H19NO |
| Molar mass | 265.356 g·mol−1 |
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HP-505 is a triple reuptake inhibitor that was investigated by Hoechst-Roussel Pharmaceuticals.[1] In mice, HP-505 was a potent inhibitor of tetrabenazine-induced ptosis which may indicate antidepressant activity.[2]
Pharmacology
| 5-HT | NE | DA | NE:5-HT | DA:5-HT |
|---|---|---|---|---|
| 0.19 ± 0.04 | 0.34 ± 0.1 | 0.66 ± 0.15 | 1.8 | 3.5 |
The inhibitory effect of HP-505 on serotonin reuptake is approximately 1.8 and 3.5 times stronger than on norepinephrine and dopamine, respectively.[1] Subsequent investigations have found that HP-505 acts on presynaptic dopamine transporters and is devoid of anticholinergic effects.[3]
Synthesis
The N-methylated analog is called HP-365 [59142-29-9].
An older synthesis is available, although more modern methods exist now:[4]
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HP-365 patent:[5]
References
- ↑ 1.0 1.1 1.2 "Effect of antidepressant agents on beta-adrenergic receptor and neurotransmitter regulatory systems". Pharmacology, Biochemistry, and Behavior 12 (6): 943–948. June 1980. doi:10.1016/0091-3057(80)90457-8. PMID 6105676.
- ↑ "Synthesis of spiro[isobenzofuran-1(3H),4'-piperidines] as potential central nervous system agents. 2. Compounds containing a heteroatom attached to nitrogen". Journal of Medicinal Chemistry 20 (4): 610–612. April 1977. doi:10.1021/jm00214a039. PMID 850252.
- ↑ "Spiroisobenzofuran Piperidine Derivatives. Interaction with Pre- and Post-Synaptic Dopaminergic Sites". Catecholamines: Basic and Clinical Frontiers. Pergamon. 1979. pp. 514–516. doi:10.1016/B978-1-4832-8363-0.50158-0. ISBN 978-1-4832-8363-0.
- ↑ "Novel Spiropiperidines as Highly Potent and Subtype Selective σ-Receptor Ligands. Part 1". Journal of Medicinal Chemistry 45 (2): 438–448. 1 January 2002. doi:10.1021/jm010992z. ISSN 0022-2623.
- ↑ Victor J. Bauer & Raymond W. Kosley, Jr., U.S. Patent 3,959,475 (1976 to CNA Holdings LLC).
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