U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H15N
Molecular Weight 101.19
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIISOPROPYLAMINE

SMILES

CC(C)NC(C)C

InChI

InChIKey=UAOMVDZJSHZZME-UHFFFAOYSA-N
InChI=1S/C6H15N/c1-5(2)7-6(3)4/h5-7H,1-4H3

HIDE SMILES / InChI

Description

Diisopropylamine (DIPA) is a secondary amine, which is used as a chemical intermediate, and catalyst for the synthesis of pesticides and pharmaceuticals. DIPA is primarily used as a precursor for the herbicides dilate and triallate, as well as certain sulfenamides used in the vulcanization of rubber. It is used for adjusting pH in cosmetic formulations, in colognes, and toilet cleaners. It is associated with tobacco either as a natural component of tobacco, pyrolysis product (in tobacco smoke), or additive for one or more types of tobacco products. When given intravenously to hypertensive patients, DIPA is known as an antihypertensive agent. DIPA exerts its action by lowering arterial blood pressure, reduction of stroke volume and cardiac output. DIPA reduced blood glucose concentrations in fasted mice and in fasted, glucose-loaded, or streptozotocin-diabetic rats. DADA (diisopropylamine dichloroacetate) was identified as an active domain of pangamic acid. DADA is a vasodilator of peripheral and cerebral arterioles. DADA also considered to aid in the detoxification of chemical and metallic metabolites, possibly by the formation of chelate-like compounds whose excretion by the kidneys is facilitated and increased. DADA increases oxygen utilization and cortical glucose uptake.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
50.9 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Rivaol
Primary
Rivaol

PubMed

Sample Use Guides

In Vivo Use Guide
60 mg/d, 120 mg/d
Route of Administration: Oral
In Vitro Use Guide
After Normal human keratinocytes (NHEK) were inoculated in a 24-well plate coated with collagen at 1x10^4 cells/ml/well and cultured under 5% CO2 at 37°C until the next day, diisopropylamine dichloroacetate (DADA) was added to each medium without EGF and BPE, followed by culturing for 4 days. The concentration of DADA in the medium was 1, 10, 30 and 100 ug/ml each. Addition of DADA to this basic medium enhanced cell growth, and its peak was shown at 10–30 ug/ml of DADA.