Ajulemic acid (also known as lenabasum) is a cannabinoid CB2 receptor agonist with the potential for treatment of skin-predominant dermatomyositis. Ajulemic acid is a synthetic cannabinoid derivative of the non-psychoactive THC metabolite 11-nor-9-carboxy-THC that shows useful analgesic and anti-inflammatory effects without causing a subjective 'high'. It is being developed for the treatment of neuropathic pain and inflammatory conditions such as arthritis. It does not however share the anti-emetic effects of other cannabinoids but may be useful for treating pain and chronic inflammatory conditions where nausea is not present.
Physicochemical Properties
| Molecular Formula | C25H36O4 |
| Molecular Weight | 400.55094 |
| Exact Mass | 400.261 |
| CAS # | 137945-48-3 |
| PubChem CID | 3083542 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.085g/cm3 |
| Boiling Point | 495.7ºC at 760mmHg |
| Flash Point | 158.5ºC |
| Vapour Pressure | 1.2E-10mmHg at 25°C |
| Index of Refraction | 1.535 |
| LogP | 6.315 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 29 |
| Complexity | 620 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | CCCCCCC(C1=CC(O)=C2[C@@H]3CC(C(=O)O)=CC[C@H]3C(OC2=C1)(C)C)(C)C |
| InChi Key | YCHYFHOSGQABSW-RTBURBONSA-N |
| InChi Code | InChI=1S/C25H36O4/c1-6-7-8-9-12-24(2,3)17-14-20(26)22-18-13-16(23(27)28)10-11-19(18)25(4,5)29-21(22)15-17/h10,14-15,18-19,26H,6-9,11-13H2,1-5H3,(H,27,28)/t18-,19-/m1/s1 |
| Chemical Name | (6aS,10aS)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-9-carboxylic acid |
| Synonyms | CPL-7075; CT-3; DMH-THC-11-OIC; HU-239; IP-751; JBT-101; DMHTHC-11OIC; AB-III-56, HU-239, IP-751, CPL 7075, CT-3, Resunab; lenabasum; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | Ajulemic acid, also known as IP 751, is a synthetic analogue of the metabolite Δ9-tetrahydrocannabinol. It is a cannabinoid receptor agonist with anti-inflammatory qualities and a Kis of 5.7 nM and 56.1 nM for hCB1 and hCB2 receptors, respectively, as well as an EC50 of 11.6 nM and 13.4 nM [1]. |
| ln Vivo | In a rat neuropathic pain model, IP 751 (0.1–1 mg/kg, oral) caused dose-dependent hyperalgesia reversal, with a maximum reversal rate of 63% and an ED50 value of 0.5 mg/kg; in a rat inflammatory pain model, the maximum reversal rate was 57% and the ED50 value was 0.7 mg/kg. With ED50 values of 5.3 mg/kg, 2.3 mg/kg, and 4.3 mg/kg in the rotarod, catalepsy, and tail flick tests, respectively, IP 751 (1, 3, and 10 mg/kg, orally) demonstrated less potency in the quadruplet test compared to the chronic pain model. |
| References |
[1]. Antihyperalgesic properties of the cannabinoid CT-3 in chronic neuropathic and inflammatory pain states in the rat. Pain. 2005 Jul;116(1-2):129-37. |
| Additional Infomation |
Ajulemic acid has been used in trials studying the treatment of Cystic Fibrosis, Dermatomyositis, and Diffuse Cutaneous Systemic Sclerosis. Ajulemic acid has been reported in Cannabis sativa with data available. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4966 mL | 12.4828 mL | 24.9657 mL | |
| 5 mM | 0.4993 mL | 2.4966 mL | 4.9931 mL | |
| 10 mM | 0.2497 mL | 1.2483 mL | 2.4966 mL |