| Identification | Back Directory | [Name]
1-pentyl-1H-indole-3-carboxylic acid | [CAS]
727421-73-0 | [Synonyms]
PB-22 3-carboxyindol metabolite
1-pentylindole-3-carboxylic acid
PB-22 3-carboxyindole metabolite
1-pentyl-1H-indole-3-carboxylic acid
1H-Indole-3-carboxylic acid, 1-pentyl-
PB-22 3-carboxyindole metabolite solution | [Molecular Formula]
C14H17NO2 | [MDL Number]
MFCD05859192 | [MOL File]
727421-73-0.mol | [Molecular Weight]
231.29 |
| Chemical Properties | Back Directory | [Boiling point ]
418.3±18.0 °C(Predicted) | [density ]
1.12±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS(pH7.2) (1:1): 0.5 mg/ml; Ethanol: 10 mg/ml | [form ]
A crystalline solid | [pka]
4.01±0.10(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Uses]
PB-22 is an analog of the potent synthetic cannabinoid, JWH 018 , which differs by having 8-hydroxyquinoline replacing the naphthalene group of JWH 018. PB-22 3-carboxyindole metabolite is expected to be a metabolite of PB-22 that would be detectable both in serum and urine. The physiological and toxicological properties of this compound are not known. This product is intended for forensic and research applications. | [Synthesis]
Step 1. Compound 34 (2.34 g, 9.44 mmol) was dissolved in 45 mL of ethanol and 5 mL of aqueous solution of KOH (85%, 1.87 g, 28.33 mmol) was added slowly and dropwise. The reaction mixture was stirred at room temperature overnight. Subsequently, KOH (85%, 1 g) was added additionally and the mixture was heated to 75 °C and maintained for 4 hours. Upon completion of the reaction, the reaction solution was acidified with 1 M HCl (2 x 25 mL) and extracted with ether (3 x 25 mL). The organic phases were combined and residual water and ethanol were removed under reduced pressure using acetonitrile as an azeotrope (about 4 times). Further concentration under reduced pressure afforded 1-pentyl-1H-indole-3-carboxylic acid (2.11 g, 92% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.27-8.20 (m, 1H), 7.93 (s, 1H), 7.42-7.37 (m, 1H), 7.33-7.28 (m, 2H), 4.17 (t, J = 7.2 Hz, 2H), 1.94-1.85 (m, 2H), 1.38-1.30 ( m, 4H), 0.90 (t, J = 6.9Hz, 3H). | [References]
[1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5086 - 5098 |
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