83002-04-4

Basic information

• Product Name: 5-(1,1-DIMETHYLHEPTYL)-2-[5-HYDROXY-2-(3-HYDROXYPROPYL)CYCLOHEXYL]PHENOL
• Synonyms: CP 55,940;(-)-CIS-3-[2-HYDROXY-4-(1,1-DIMETHYLHEPTYL)PHENYL]-TRANS-4-(3-HYDROXYPHENYL) CYCLOHEXANOL;(-)-CIS-3-[2-HYDROXY-4-(1,1-DIMETHYLHEPTYL)PHENYL]-TRANS-4-(3-HYDROXYPROPYL)CYCLOHEXANOL;5-(1,1-DIMETHYLHEPTYL)-2-[5-HYDROXY-2-(3-HYDROXYPROPYL)CYCLOHEXYL]PHENOL;(-)-Cis-3-[2-Hydroxy-4-(1,1-Di;(1R)-3β-[2-Hydroxy-4-(1,1-dimethylheptyl)phenyl]-4α-(3-hydroxypropyl)cyclohexane-1β-ol;3β-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-4α-(3-hydroxypropyl)cyclohexan-1β-ol;2-[5-hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-Methyloctan-2-yl)phenol
• CAS NO: 83002-04-4
• Molecular Formula: C24H40O3
• Molecular Weight: 376.57
• Product Categories: Cannabinoid receptor;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pfizer Compounds;Pharmaceuticals
• Mol File: 83002-04-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 65-68 °C
• Boiling Point: 494.4 °C at 760 mmHg
• Flash Point: 209.2 °C
• Appearance: /solid
• Density: 1.026 g/cm³
• Vapor Pressure: 1.36E-10mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: 2-8°C
• Solubility: DMSO: 15 mg/mL, soluble
• PKA: 10.25±0.40(Predicted)
• CAS DataBase Reference: 5-(1,1-DIMETHYLHEPTYL)-2-[5-HYDROXY-2-(3-HYDROXYPROPYL)CYCLOHEXYL]PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(1,1-DIMETHYLHEPTYL)-2-[5-HYDROXY-2-(3-HYDROXYPROPYL)CYCLOHEXYL]PHENOL(83002-04-4)
• EPA Substance Registry System: 5-(1,1-DIMETHYLHEPTYL)-2-[5-HYDROXY-2-(3-HYDROXYPROPYL)CYCLOHEXYL]PHENOL(83002-04-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 83002-04-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 83002-04-4 differently. You can refer to the following data:
1. CP 55,940 is a cannabinoid agonist which is considerably more potent than Δ9-THC in both behavioral tests and receptor binding assays. Displays high and roughly equal affinity for both central and peripheral cannabinoid receptors (Ki = 0.6 - 5.0 and 0.7 - 2.6 nM at CB1 and CB2 respectively; EC50 values are 0.2, 0.3 and 5 nM at CB1, CB2 and GRP55 respectively). Controlled substance.
2. (+)-CP 55940 is the enantiomer of (C781415), a cannabinoid agonist. Both CP 55,940 and (+)-CP 55940 bind to CB receptors but only CP-55,940 elicits a biological response via the receptors. However, ( +)-CP 55940 shows the same antinociceptive effects as its enantiomer.
3. CP-55940 has been used as a cannabinoid agonists in Chinese hamster ovary (CHO) expressing cannabinoid receptor 2(CB2).

Biological Activity

Cannabinoid agonist which is considerably more potent than Δ 9 -THC in both behavioral tests and receptor binding assays. Displays high and roughly equal affinity for both central and peripheral cannabinoid receptors (K i = 0.6-5.0 and 0.7-2.6 nM at CB 1 and CB 2 respectively; EC 50 values are 0.2, 0.3 and 5 nM at CB 1 , CB 2 and GRP55 respectively). Also available as part of the Cannabinoid Receptor Agonist Tocriset? .

Biochem/physiol Actions

CP-55940 is a nonclassical cannabinoids (NCCs), which lack the tetrahydropyran ring. CP-55940, a derivative of CP-47,497 is enantioselective. Due to its amphipathic nature, CP-55940 tethers in biological membrane making it favourable for the cannabinoid receptor interaction. CP-55940 belongs to the cyclohexylphenol category and modulates the brain lipidome leading to dysregulation especially during adolescence. It inhibits capsaicin-evoked sensitization of nociceptive and spinal dorsal horn neurons.

InChI:InChI=1/C24H40O3/c1-4-5-6-7-14-24(2,3)19-11-13-21(23(27)16-19)22-17-20(26)12-10-18(22)9-8-15-25/h11,13,16,18,20,22,25-27H,4-10,12,14-15,17H2,1-3H3/t18-,20-,22-/m1/s1

Upstream product

• 591-31-1 3-methoxy-benzaldehyde 
• 106591-04-2 1-(3-methoxyphenyl)heptan-1-ol 
• 100863-37-4 1-(3-methoxyphenyl)heptan-1-one 
• 111-25-1 1-bromo-hexane 
• 1374219-26-7 O-(1S,2S)-2-[2-methoxy-4-(2-methyloctan-2-yl)phenyl]-4-oxocyclohexyl S-methyl carbonodithioate 
• 1374219-25-6 O-(7S,8S)-7-[2-methoxy-4-(2-methyloctan-2-yl)phenyl]-1,4-dioxaspiro[4.5]decan-8-yl S-methyl carbonodithioate 
• 1374219-10-9 (7S,8S)-7-(2-methoxy-4-(2-methyloctan-2-yl)phenyl)-1,4-dioxaspiro[4.5]decan-8-ol 
• 1374219-11-0 C₂₄H₃₆O₄ 
• 1374219-24-5 7-(2-methoxy-4-(2-methyloctan-2-yl)phenyl)-1,4-dioxaspiro[4.5]dec-6-en-8-one 
• 1374219-14-3 7-iodo-1,4-dioxaspiro[4.5]dec-6-en-8-one 
• 1374219-15-4 2-methoxy-4-(2-methyloctan-2-yl)phenylboronic acid 
• 4683-24-3 1,4-dioxa-spiro[4.5]dec-6-en-8-one 
• 87613-50-1 3-(1,1-dimethylheptyl)-5-methoxyphenol 
• 181764-33-0 1-bromo-4-(1,1-dimethylheptyl)-2-methoxybenzene 

Relevant articles and documents

Enantioselective synthesis of (-)-CP-55940 via ruthenium-catalyzed asymmetric hydrogenation of ketones

A new and efficient catalytic asymmetric synthesis of the potent cannabinoid receptor agonist (-)-CP-55940 has been developed by using ruthenium-catalyzed asymmetric hydrogenation of racemic α-aryl ketones via dynamic kinetic resolution (DKR) as a key step. With RuCl2-SDPs/ diamine [SDPs=7,7'-bis(diarylphophino)-1,1'-spirobiindane] catalysts the asymmetric hydrogenation of racemic α-arylcyclohexanones via DKR provided the corresponding cis-β-arylcyclohexanols in high yields with up to 99.3% ee and >99:1 cis-selectivities. Both ethylene ketal group at the cyclohexane ring and ortho-methoxy group at the phenyl ring of the substrates 6 have little effect on the selectivity and reactivity of the hydrogenations. Based on this highly efficient asymmetric ketone hydrogenation, (-)-CP-55940 was synthesized in 13 steps (the longest linear steps) in 14.6% overall yield starting from commercially available 3-methoxybenzaldehyde and 1,4-cyclohexenedione monoethylene acetal. Copyright

2-Hydroxy-4-(substituted) phenyl cycloalkanes and derivatives

Compounds having the formula STR1 R1 is hydrogen, benzyl or an ester moiety; Y is --CH(R2 ")CH(R2)-- or--CH(R3)CH2 --; R2 " is hydrogen or methyl; R2 is OH or X-substituted (C1-6)alkyl; R3 is OH, cyano or X-substituted (C1-3) alkyl; X is --OR6, --SR6, --S(O)R6, --S(O)2 R6, --NR6 R7, --COOR7, --CONR7 R8 or oxo; with the proviso that when X is --NR6 R7, --COOR7 or --CONR7 R8, said group is located on the terminal carbon atom of R2 or R3 ; R6 is hydrogen, (C1-6)alkyl or acetyl; each of R7 and R8 is hydrogen or (C1-6)alkyl; s is an integer of 1 or 2; with the proviso that when R6 is acetyl, R7 is hydrogen and X is other than S(O)R6 or S(O)2 R6 ; Z--W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain, and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.