Synonym
SDB-001; SDB 001; SDB001; JWH 018 adamantyl carboxamide; JWH018; JWH-018; APICA; 2NE1;
IUPAC/Chemical Name
N-(1-Adamantyl)-1-pentyl-1H-indole-3-carboxamide
InChi Key
MDJYHWLDDJBTMX-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H32N2O/c1-2-3-6-9-26-16-21(20-7-4-5-8-22(20)26)23(27)25-24-13-17-10-18(14-24)12-19(11-17)15-24/h4-5,7-8,16-19H,2-3,6,9-15H2,1H3,(H,25,27)
SMILES Code
O=C(C1=CN(CCCCC)C2=C1C=CC=C2)NC34CC5CC(C4)CC(C5)C3
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, DMF, and ethanol
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
The endocannabinoid system consists of at least two cannabinoid (CB) receptors, namely, the CB1 and CB2 receptors. Stimulation of the CB1 receptor leads to modulation of feeding behavior, through a proposed mechanism of N-type and P/Q-type calcium channel blockade while activating the inwardly rectifying potassium channels, implicating an important role for CB1 receptor in obesity and metabolic disorders through release of neuromodulators. However, the usage of the drugs may have severe side effects on the CNS such as depression, anxiety, and suicidal thoughts. Selective CB2 agonists represent an attractive therapeutic strategy for the treatment of a variety of diseases such as MS without psychiatric side effects mediated by the CB1 receptor.
Biological target:
SDB-001 potently activates both the central CB1 and peripheral CB2 receptors (Ki = 9.0 and 2.94 nM, respectively).
In vitro activity:
SDB-001 produces neurotoxicity, and this study demonstrated that SDB-001 produced oxidative stress in human SH-SY5Y neuronal cells. SDB-001 significantly reduced glutathione reductase and catalase activities. SDB-001 treatment significantly decreased glutathione concentrations, significantly increased protein carbonylation, and significantly increased malondialdehyde concentrations.
Reference: Toxicol Res (Camb). 2020 Nov 4;9(6):734-740. https://pubmed.ncbi.nlm.nih.gov/33447358/
In vivo activity:
High doses of SDB-001 induced psychotic-like symptoms and altered neuroplasticity and the endocannabinoid system in male CD-1 mice. Repeated SDB-001 treatment resulted in psychomotor agitation, decreased social dominance, recognition memory, and prepulse inhibition. SDB-001 disrupted hippocampal LTP, reduced BDNF expression, synaptic NMDA receptor subunits, and PSD95 levels. SDB-001 decreased CB1 receptor density in the hippocampus and induced long-term changes in AEA and 2-AG levels.
Reference: Br J Pharmacol. 2023 Nov;180(21):2777-2801. https://pubmed.ncbi.nlm.nih.gov/37311647/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
30.0 |
82.30 |
|
| DMSO |
30.0 |
82.00 |
|
| Ethanol |
1.0 |
2.74 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
364.53
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Sezer Y, Jannuzzi AT, Huestis MA, Alpertunga B. In vitro assessment of the cytotoxic, genotoxic and oxidative stress effects of the synthetic cannabinoid JWH-018 in human SH-SY5Y neuronal cells. Toxicol Res (Camb). 2020 Nov 4;9(6):734-740. doi: 10.1093/toxres/tfaa078. PMID: 33447358; PMCID: PMC7786167.
2. Patton AL, Seely KA, Yarbrough AL, Fantegrossi W, James LP, McCain KR, Fujiwara R, Prather PL, Moran JH, Radominska-Pandya A. Altered metabolism of synthetic cannabinoid JWH-018 by human cytochrome P450 2C9 and variants. Biochem Biophys Res Commun. 2018 Apr 6;498(3):597-602. doi: 10.1016/j.bbrc.2018.03.028. Epub 2018 Mar 10. PMID: 29522717; PMCID: PMC6425723.
3. Bilel S, Zamberletti E, Caffino L, Tirri M, Mottarlini F, Arfè R, Barbieri M, Beggiato S, Boccuto F, Bernardi T, Casati S, Brini AT, Parolaro D, Rubino T, Ferraro L, Fumagalli F, Marti M. Cognitive dysfunction and impaired neuroplasticity following repeated exposure to the synthetic cannabinoid JWH-018 in male mice. Br J Pharmacol. 2023 Nov;180(21):2777-2801. doi: 10.1111/bph.16164. Epub 2023 Jul 13. PMID: 37311647.
4. Izquierdo-Luengo C, Ten-Blanco M, Ponce-Renilla M, Perezzan R, Pereda-Pérez I, Berrendero F. Adolescent exposure to the Spice/K2 cannabinoid JWH-018 impairs sensorimotor gating and alters cortical perineuronal nets in a sex-dependent manner. Transl Psychiatry. 2023 May 25;13(1):176. doi: 10.1038/s41398-023-02469-4. PMID: 37225721; PMCID: PMC10209055.
In vitro protocol:
1. Sezer Y, Jannuzzi AT, Huestis MA, Alpertunga B. In vitro assessment of the cytotoxic, genotoxic and oxidative stress effects of the synthetic cannabinoid JWH-018 in human SH-SY5Y neuronal cells. Toxicol Res (Camb). 2020 Nov 4;9(6):734-740. doi: 10.1093/toxres/tfaa078. PMID: 33447358; PMCID: PMC7786167.
2. Patton AL, Seely KA, Yarbrough AL, Fantegrossi W, James LP, McCain KR, Fujiwara R, Prather PL, Moran JH, Radominska-Pandya A. Altered metabolism of synthetic cannabinoid JWH-018 by human cytochrome P450 2C9 and variants. Biochem Biophys Res Commun. 2018 Apr 6;498(3):597-602. doi: 10.1016/j.bbrc.2018.03.028. Epub 2018 Mar 10. PMID: 29522717; PMCID: PMC6425723.
In vivo protocol:
1. Bilel S, Zamberletti E, Caffino L, Tirri M, Mottarlini F, Arfè R, Barbieri M, Beggiato S, Boccuto F, Bernardi T, Casati S, Brini AT, Parolaro D, Rubino T, Ferraro L, Fumagalli F, Marti M. Cognitive dysfunction and impaired neuroplasticity following repeated exposure to the synthetic cannabinoid JWH-018 in male mice. Br J Pharmacol. 2023 Nov;180(21):2777-2801. doi: 10.1111/bph.16164. Epub 2023 Jul 13. PMID: 37311647.
2. Izquierdo-Luengo C, Ten-Blanco M, Ponce-Renilla M, Perezzan R, Pereda-Pérez I, Berrendero F. Adolescent exposure to the Spice/K2 cannabinoid JWH-018 impairs sensorimotor gating and alters cortical perineuronal nets in a sex-dependent manner. Transl Psychiatry. 2023 May 25;13(1):176. doi: 10.1038/s41398-023-02469-4. PMID: 37225721; PMCID: PMC10209055.
1: Banister SD, Wilkinson SM, Longworth M, Stuart J, Apetz N, English K, Brooker L, Goebel C, Hibbs DE, Glass M, Connor M, McGregor IS, Kassiou M. The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse. ACS Chem Neurosci. 2013 Jul 17;4(7):1081-92. doi: 10.1021/cn400035r. Epub 2013 Apr 17. PubMed PMID: 23551277; PubMed Central PMCID: PMC3715837.
1: Shi Y, Duan YH, Ji YY, Wang ZL, Wu YR, Gunosewoyo H, Xie XY, Chen JZ, Yang F, Li J, Tang J, Xie X, Yu LF. Amidoalkylindoles as Potent and Selective Cannabinoid Type 2 Receptor Agonists with in Vivo Efficacy in a Mouse Model of Multiple Sclerosis. J Med Chem. 2017 Aug 3. doi: 10.1021/acs.jmedchem.7b00724. [Epub ahead of print] PubMed PMID: 28726401.
