70434-82-1

Usage

Uses

Used in Pharmaceutical Industry:
CP 47,497 is used as a cannabinoid receptor ligand for its potent binding affinity to the central cannabinoid (CB1) receptor. This characteristic makes it a valuable compound for research and development in the field of cannabinoid-based therapies.
Used in Medical Research:
CP 47,497 is used as a research tool for studying the effects of cannabinoid receptor activation on various physiological processes. Its high affinity for the CB1 receptor allows scientists to investigate the potential therapeutic applications of cannabinoid-based treatments for a range of medical conditions, including pain management, neurodegenerative diseases, and mood disorders.
Used in Pain Management:
CP 47,497 is used as an analgesic agent due to its equivalent potency to Δ9-THC in pain relief. This property makes it a potential candidate for the development of novel pain management therapies, particularly for conditions that are not adequately addressed by current treatments.
Used in Neurodegenerative Disease Research:
CP 47,497 is used as a research compound to explore the potential neuroprotective effects of cannabinoid receptor activation in neurodegenerative diseases such as Alzheimer's, Parkinson's, and multiple sclerosis. Its ability to modulate CB1 receptor activity may provide insights into the development of new therapeutic strategies for these conditions.
Used in Mood Disorder Research:
CP 47,497 is used as a research tool to investigate the role of the endocannabinoid system in mood regulation and the potential therapeutic applications of cannabinoid-based treatments for mood disorders such as depression and anxiety. Its interaction with the CB1 receptor may help to elucidate the underlying mechanisms involved in mood regulation and contribute to the development of more effective treatments for these conditions.

Biological Activity

Potent CB 1 receptor agonist (K i = 2.2 nM). Display 3-28-fold > potency than Δ 9 -THC . Exhibits analgesic, motor depressant, anticonvulsant and hypothermic effects in vivo .

InChI:InChI=1/C21H34O2/c1-4-5-6-7-13-21(2,3)17-11-12-19(20(23)15-17)16-9-8-10-18(22)14-16/h11-12,15-16,18,22-23H,4-10,13-14H2,1-3H3/t16-,18+/m1/s1

Synthetic route

(Z)-3-<2-(benzyloxy)-4-(1,1-dimethylheptyl)phenyl>cyclohexanol (70434-49-0) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal In ethanol under 760 Torr; for 2h;	77%
With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal

cyclohexenone (930-68-7) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: CuI / tetrahydrofuran / 0.5 h / -3 °C 2: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 3: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme
Multi-step reaction with 3 steps 1: (i) Mg, (ii) CuI, (iii) /BRN= 1280477/ 2: sodium tetrahydroborate 3: hydrogen; sodium hydrogencarbonate / palladium on activated charcoal View Scheme
Multi-step reaction with 3 steps 1: (i) Mg, (ii) CuI, (iii) /BRN= 1280477/ 2: sodium tetrahydroborate 3: hydrogen; sodium hydrogencarbonate / palladium on activated charcoal View Scheme

1-bromo-2-benzyloxy-4-(1,1-dimethylheptyl)benzene (70120-16-0) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: Mg / tetrahydrofuran / 20 h / Heating 2: CuI / tetrahydrofuran / 0.5 h / -3 °C 3: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 4: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme
Multi-step reaction with 3 steps 1: (i) Mg, (ii) CuI, (iii) /BRN= 1280477/ 2: sodium tetrahydroborate 3: hydrogen; sodium hydrogencarbonate / palladium on activated charcoal View Scheme
Multi-step reaction with 3 steps 1: (i) Mg, (ii) CuI, (iii) /BRN= 1280477/ 2: sodium tetrahydroborate 3: hydrogen; sodium hydrogencarbonate / palladium on activated charcoal View Scheme

3-<2-(benzyloxy)-4-(1,1-dimethylheptyl)phenyl>cyclohexanone (70434-13-8) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 2: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate 2: hydrogen; sodium hydrogencarbonate / palladium on activated charcoal View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate 2: hydrogen; sodium hydrogencarbonate / palladium on activated charcoal View Scheme

2-(3-hydroxyphenyl)-2-methyloctane (70120-12-6) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
Multi-step reaction with 6 steps 1: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 2: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 3: Mg / tetrahydrofuran / 20 h / Heating 4: CuI / tetrahydrofuran / 0.5 h / -3 °C 5: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 6: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

2-(4-bromo-3-hydroxyphenyl)-2-methyloctane (70120-14-8) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 2: Mg / tetrahydrofuran / 20 h / Heating 3: CuI / tetrahydrofuran / 0.5 h / -3 °C 4: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 5: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

2-(3-benzyloxyphenyl)-2-methylpropionaldehyde (70120-09-1) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions

Yield

Multi-step reaction with 8 steps 1: 57 percent / DMSO, NaOH / 4 h / 15 °C 2: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 3: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 4: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 5: Mg / tetrahydrofuran / 20 h / Heating 6: CuI / tetrahydrofuran / 0.5 h / -3 °C 7: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 8: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

2-<3-(benzyloxy)phenyl>-2-methylpropionitrile (70120-08-0) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions

Yield

Multi-step reaction with 9 steps 1: 1.) diisobutylaluminium hydride (DIBAL), 2.) aq. H2SO4 / 1.) THF, hexane, 25 deg C, 2 h, 2.) THF, hexane, 25 deg C, 2 h 2: 57 percent / DMSO, NaOH / 4 h / 15 °C 3: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 4: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 5: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 6: Mg / tetrahydrofuran / 20 h / Heating 7: CuI / tetrahydrofuran / 0.5 h / -3 °C 8: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 9: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

1-(benzyloxy)-3-(1,1-dimethyl-2-heptenyl)benzene (70120-10-4) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions

Yield

Multi-step reaction with 7 steps 1: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 2: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 3: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 4: Mg / tetrahydrofuran / 20 h / Heating 5: CuI / tetrahydrofuran / 0.5 h / -3 °C 6: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 7: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

pentyltriphenylphosphonium bromide (21406-61-1) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions

Yield

Multi-step reaction with 8 steps 1: 57 percent / DMSO, NaOH / 4 h / 15 °C 2: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 3: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 4: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 5: Mg / tetrahydrofuran / 20 h / Heating 6: CuI / tetrahydrofuran / 0.5 h / -3 °C 7: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 8: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

C22H29BrMgO → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: CuI / tetrahydrofuran / 0.5 h / -3 °C 2: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 3: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

Upstream product

• 70434-49-0 (Z)-3-<2-(benzyloxy)-4-(1,1-dimethylheptyl)phenyl>cyclohexanol 
• 70120-16-0 1-bromo-2-benzyloxy-4-(1,1-dimethylheptyl)benzene 
• 70120-09-1 2-(3-benzyloxyphenyl)-2-methylpropionaldehyde 
• 70120-08-0 2-<3-(benzyloxy)phenyl>-2-methylpropionitrile 
• 70120-10-4 1-(benzyloxy)-3-(1,1-dimethyl-2-heptenyl)benzene 
• 21406-61-1 pentyltriphenylphosphonium bromide 
• 70120-14-8 2-(4-bromo-3-hydroxyphenyl)-2-methyloctane 
• 70120-12-6 2-(3-hydroxyphenyl)-2-methyloctane 
• 70434-13-8 3-<2-(benzyloxy)-4-(1,1-dimethylheptyl)phenyl>cyclohexanone 
• 930-68-7 cyclohexenone 

Relevant academic research and scientific papers

A Cannabinoid Derived Prototypical Analgesic

The synthesis and analgesic testing of 3-cyclohexanol (1) are described.Prior (SAR) studies led us to conclude that the pyran ring of 9-nor-9β-hydroxyhexahydrocannabinol (HHC) was not necessary for the expression of biological activity in this series of cannabinoids.Analysis of models and the use of molecular mechanics calculations suggested that a simpler compound, such as 1, would possess the biological activity of HHC.Compound 1 was prepared in nine steps from acetonitrile (2).Biological testing in five models of pain shows that compound 1 and morphine are equally potent as analgesics and demonstrates that the pyran ring of HHC is not necessary for biological activity.Further simplification of 1 was pursued by the synthesis of 4--2-pentanol (17), but this derivative exhibits significantly reduced analgesic activity.