83002-04-4 Usage
Description
5-(1,1-DIMETHYLHEPTYL)-2-[5-HYDROXY-2-(3-HYDROXYPROPYL)CYCLOHEXYL]PHENOL is a complex organic compound with a unique molecular structure. It is characterized by a phenol core with various substituents, including a 1,1-dimethylheptyl group and a hydroxylated cyclohexyl group with a hydroxypropyl side chain. 5-(1,1-DIMETHYLHEPTYL)-2-[5-HYDROXY-2-(3-HYDROXYPROPYL)CYCLOHEXYL]PHENOL has potential applications in various fields due to its unique chemical properties.
Uses
Used in Pharmaceutical Industry:
5-(1,1-DIMETHYLHEPTYL)-2-[5-HYDROXY-2-(3-HYDROXYPROPYL)CYCLOHEXYL]PHENOL is used as a cannabinoid agonist for its high affinity and potency in binding to both central and peripheral cannabinoid receptors (CB1 and CB2). It is considerably more potent than Δ9-THC in behavioral tests and receptor binding assays, making it a valuable compound for the development of new therapeutic agents targeting the endocannabinoid system.
Used in Research Applications:
In research settings, 5-(1,1-DIMETHYLHEPTYL)-2-[5-HYDROXY-2-(3-HYDROXYPROPYL)CYCLOHEXYL]PHENOL is used as a tool compound to study the effects and mechanisms of action of cannabinoid receptors. It has been utilized in Chinese hamster ovary (CHO) cells expressing cannabinoid receptor 2 (CB2) to investigate the role of CB2 receptors in various biological processes.
Used in Drug Development:
5-(1,1-DIMETHYLHEPTYL)-2-[5-HYDROXY-2-(3-HYDROXYPROPYL)CYCLOHEXYL]PHENOL is also used in the development of new drugs targeting the endocannabinoid system. Its high potency and selectivity for cannabinoid receptors make it a promising candidate for the treatment of various disorders, including pain, inflammation, and neurodegenerative diseases.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 83002-04-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,3,0,0 and 2 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 83002-04:
(7*8)+(6*3)+(5*0)+(4*0)+(3*2)+(2*0)+(1*4)=84
84 % 10 = 4
So 83002-04-4 is a valid CAS Registry Number.
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
83002-04-4Relevant articles and documents
Enantioselective synthesis of (-)-CP-55940 via ruthenium-catalyzed asymmetric hydrogenation of ketones
Cheng, Li-Jie,Xie, Jian-Hua,Wang, Li-Xin,Zhou, Qi-Lin
, p. 1105 - 1113 (2012/05/21)
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
-
, (2008/06/13)
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.
