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Details

Stereochemistry ACHIRAL
Molecular Formula C18H29NO3
Molecular Weight 307.4278
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDROCAPSAICIN

SMILES

COC1=C(O)C=CC(CNC(=O)CCCCCCC(C)C)=C1

InChI

InChIKey=XJQPQKLURWNAAH-UHFFFAOYSA-N
InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)

HIDE SMILES / InChI

Description

Dihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers. Like capsaicin, it contributes to the spicy taste of chili peppers, although it is less potent than capsacian. Dihydrocapsaicin has been shown to induce hypothermia in rats, a property which may help protect victims of stroke and cardiac arrest.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Twenty healthy subjects ingested a single dose of Capsimax capsaicinoid supplement after 12 hours of fasting. The supplement contains 100 mg of encapsulated beadlets, standardized to 2% capsaicinoids, of which 1.2-1.35% was capsaicin, 0.6-0.8% was dihydrocapsaicin, and 0.1-0.2% was nordihydrocapsaicin. Fasting blood samples were collected during each visit; 30 minutes following a rest period and before supplement intake (Pre); 2 hours post intake (2 hr); one minute following the cessation of 30 minutes of exercise performed at 65% of maximal heart rate reserve (2.5 hr); and 90 minutes following the cessation of exercise (4 hr). Heart rate (HR), systolic (SBP) and diastolic (DBP) blood pressure were recorded at all times. Blood glycerol was higher with Capsimax than for placebo at 4 hr and FFA was higher with Capsimax than for placebo at 2 hr.
Route of Administration: Oral
In Vitro Use Guide
Human lung carcinoma cell line (A549) was maintained on DMEM supplemented with 9% heat-inactivated fetal bovine serum and 10 micro-g/mL gentamicin. The cells were grown at 37 deg-C in a 5% CO2 atmosphere. Cells were treated with increasing concentrations (100, 200, 300, and 400 micro-M) of dihydrocapsaicin dissolved in DMSO, fo 6, 12, 24, or 48 hours. After exposures, the culture mediums were collected and processed for metabolite analysis. The viability of cultured cells was determined by the MTT-reduction method. Dihydrocapsaicin decreased cell viability in a dose- and time-dependent way. The concentration corresponding to the EC50 was about 400 micro-M. The decrease in the viability by dihydrocapsaicin reached 50% within 6 hours.