TETRAHYDROPIPERINE

SKU: orb1301491

Description

TETRAHYDROPIPERINE

Research Area

Metabolism Research, Pharmacology & Drug Discovery

Key Properties

• CAS Number: 23434-88-0
• MW: 289.37
• Purity: 99.61%
• Formula: C₁₇H₂₃NO₃
• SMILES: O=C(CCCCc1ccc2OCOc2c1)N1CCCCC1
• Target: Cytochromes P450,TRP/TRPV Channel
• Solubility: DMSO:57 mg/mL (196.98 mM)

Bioactivity

• Target IC50:
  CYP450:23 µM |MOCD:25 µM|TRPV1:6.3 µM
• In Vivo:
  TETRAHYDROPIPERINE is an agonist of transient receptor potential vanilloid type 1 (TRPV1; EC50 = 6.3 μM). It inhibits the cytochrome P450 (CYP) isoform CYP1A1/arylhydrocarbon hydroxylase (AHH; IC50 = 23 μM) and 7-methoxycoumarin O-demethylase (MOCD) activity (IC50 = 25 μM) in rat liver microsomes.Tetrahydropiperine increases skin pigmentation in a mouse model of vitiligo when 100 μl of a 175 mM solution is administered topically, an effect that can be enhanced by subsequent suberythemal ultraviolet radiation (UVR).
• Animal Research:
  The test compounds were PIP [5-(3,4-methylenedioxyphenyl)-2,4-pentadienoylpiperidine], tetrahydropiperine [THP, 5-(3,4-methylenedioxyphenyl)-pentanoylpiperidine], a cyclohexyl analogue of piperine [CHP, 5-(3,4-methylenedioxyphenyl)-2,4-pentadienoylcyclohexylamine], and reduced CHP [rCHP, 5-(3,4-methylenedioxyphenyl)-2,4-pentanoylcyclohexylamine]. Sparsely pigmented, HRA/Skh-II mice were randomized to receive topical treatment with test compounds or vehicle twice a day for five days a week, with or without ultraviolet (UV) irradiation on 3 days a week. Treatment was either continuous or interrupted to evaluate fading and repigmentation. Skin inflammation and pigmentation were evaluated regularly during treatment. DOPA+ melanocytes were determined histologically at the termination of treatment.

Storage & Handling

• Storage: keep away from direct sunlight | Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Cosmoperine, Cytochrome P450, CYP450, CYP, CYP1A1, CYPs, aryl pentanamide, arylhydrocarbon, AHH, Inhibitor, inhibit, Htrpv1, hydroxylase, Piperine, TETRAHYDROPIPERINE, TRPChannel, TRPV Channel, TRP Channel, TRPVChannel

Compound Identifiers

PubChem CID

581676