The enantiomeric purity of this compound is not a product specification determined for batch release. However, the range of optical rotation value needed for batch release, as indicated in the lot specific Certificate of Analysis, is very close to the published literature value for the (-) enantiomer (Org Lett. 2005 Sep 15;7(19):4181-3).
C1112
CP-55940
>98% (HPLC), powder
Synonym(s):
5-(1,1-Dimethylheptyl)-2-[5-hydroxy-2-(3-hydroxypropyl)cyclohexyl]phenol
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About This Item
Empirical Formula (Hill Notation):
C24H40O3
CAS Number:
Molecular Weight:
376.57
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.
Recommended Products
Quality Level
Assay
>98% (HPLC)
form
powder
optical activity
[α]/D -24 to -30°, c = 0.2 in chloroform-d
drug control
regulated under CDSA - not available from Sigma-Aldrich Canada
storage condition
desiccated
solubility
DMSO: 15 mg/mL
H2O: slightly soluble
storage temp.
2-8°C
SMILES string
CCCCCCC(C)(C)c1ccc([C@@H]2C[C@H](O)CC[C@H]2CCCO)c(O)c1
InChI
1S/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
InChI key
YNZFFALZMRAPHQ-SYYKKAFVSA-N
Gene Information
human ... CNR1(1268) , CNR2(1269)
rat ... Cnr1(25248)
Application
CP-55940 has been used as a cannabinoid agonists in Chinese hamster ovary (CHO) expressing cannabinoid receptor 2(CB2).[1]
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.[2] CP-55940 belongs to the cyclohexylphenol category and modulates the brain lipidome leading to dysregulation especially during adolescence.[3] It inhibits capsaicin-evoked sensitization of nociceptive and spinal dorsal horn neurons.[4]
CP-55940 is a selective cannabinoid receptor agonist.
Features and Benefits
This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Certificates of Analysis (COA)
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Customers Also Viewed
Cannabinoid agonist, CP 55,940, prevents capsaicin-induced sensitization of spinal cord dorsal horn neurons
Johanek LM and Simone DA
Journal of Neurophysiology, 93(2), 989-997 (2005)
Broad and Region-Specific Impacts of the Synthetic Cannabinoid CP 55,940 in Adolescent and Adult Female Mouse Brains
Leishman E, et al.
Frontiers in Molecular Neuroscience, 11, 436-436 (2018)
David R Maguire et al.
Psychopharmacology, 235(8), 2357-2365 (2018-06-04)
Cannabinoid receptor agonists such as delta-9-tetrahydrocannabinol (Δ9-THC) enhance the antinociceptive potency of mu opioid receptor agonists such as morphine, indicating that opioid/cannabinoid mixtures might be effective for treating pain. However, such enhancement will be beneficial only if cannabinoids do not
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The conformational properties of the highly selective cannabinoid receptor ligand CP-55,940
Xie XQ, et al.
The Journal of Biological Chemistry, 271(18), 10640-10647 (1996)
Articles
A large variety of cannabinoid drug standards, along with an HPLC method with the Supelco Ascentis® Express RP-Amide column, are presented in this article.
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Can you please specify whether C1112 (CP 55,940) is a +, a -, or +/- (racemic) enantiomer?
1 answer-
Helpful?
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Could you please specify whether C1112 (CP 55,940) is a +, a -, or +/- (racemic) enantiomer? Thank you!
1 answer-
The enantiomeric purity of this compound is not a product specification determined for batch release. However, the range of optical rotation required for batch release, as indicated in the lot-specific Certificate of Analysis, is very close to the published literature value for the (-) enantiomer.
Org Lett. 2005 Sep 15;7(19):4181-3.
Helpful?
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