TETRAHYDROPIPERINE

SKU: orb1301491

Description

TETRAHYDROPIPERINE

Research Area

Metabolism Research, Pharmacology & Drug Discovery

Images & Validation

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Key Properties

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

Bioactivity

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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

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Storage	-20°C
Expiration Date	12 months from date of receipt.
Disclaimer	For research use only

Alternative Names

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

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Compound Identifiers

PubChem CID

581676 ↗

Key Properties

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No computed properties available.

Protocol Information

Find More Protocols

Purity:	>98% (HPLC)
CAS Number:	23434-88-0
MW:	289.37
Formula:	C₁₇H₂₃NO₃

TETRAHYDROPIPERINE

Description

Research Area

Images & Validation

Key Properties

Bioactivity

Storage & Handling

Alternative Names

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