Draft:U-32,802A
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| Identifiers | |
|---|---|
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| Chemical and physical data | |
| Formula | C22H23F2NO |
| Molar mass | 355.429 g·mol−1 |
| 3D model (JSmol) | |
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U-32,802A is an antipsychotic tranquilizer of the butyrophenone class. It was developed by Daniel Lednicer at Upjohn Pharmaceuticals in the early part of the 1970’s. Whereas related agents are based on a 4-aryl-piperidine central ring system, U-32,802A is an 4-aryl-cyclohexylamine, which might be expected to offer a unique pharmacological profile. Based on the available pharmacological data, U-32,802A was hypothesized to act primarily at the presynaptic organelles for storage of monoamines in a way similar to tetrabenazine.[1][2][3]
Synthesis
[edit]The chemical synthesis of U-32,802A was disclosed in a pair of patents>[4][5]
- 4-Fluorophenylmagnesium bromide [352-13-6] (1)
- 4-Hydroxycyclohexanone [13482-22-9] (2)
- 1-(4-Fluorophenyl)-1,4-cyclohexanediol, PC21528214 (3)
- 4-(4-fluorophenyl)-4-hydroxycyclohexan-1-one [36716-69-5] (4)
- 4-(4-fluorophenyl)cyclohex-3-en-1-one [36716-73-1] (5)
- 4-(p-Fluorophenyl)-3-cyclohexen-1-ol, PC21534465 (6)
- mesyl (7)
- azide (8)
- 4-(4-Fluorophenyl)cyclohex-3-en-1-amine [764586-33-6] (9)
- 1-(4-Chloro-1,1-dimethoxybutyl)-4-fluorobenzene [57390-39-3] (10)
References
[edit]- ^ Lahti RA, Lednicer D (June 1974). "Effect of a butyrophenone derivative, U-32,802A, on brain biogenic amines". Biochemical Pharmacology. 23 (12): 1701–5. doi:10.1016/0006-2952(74)90397-9. PMID 4842658.
- ^ Fuenmayor LD, Vogt M (October 1979). "The influence of cerebral 5-hydroxytryptamine on catalepsy induced by brain-amine depleting neuroleptics or by cholinomimetics". British Journal of Pharmacology. 67 (2): 309–18. doi:10.1111/j.1476-5381.1979.tb08681.x. PMC 2043889. PMID 40649.
- ^ Fuenmayor LD, Vogt M (September 1979). "Production of catalepsy and depletion of brain monoamines by a butyrophenone derivative". British Journal of Pharmacology. 67 (1): 115–22. doi:10.1111/j.1476-5381.1979.tb16114.x. PMC 2043615. PMID 574039.
- ^ D Lednicer, GB1327691 (1973 to Pharmacia and Upjohn Co).
- ^ Daniel Portage Mich Lednicer (V St A), GB1311580 (1973 to Pharmacia and Upjohn Co).