42971-15-3

Usage

Family

Benzodioxole

Structure

Complex, aromatic

Natural Occurrence

Found in various plant species such as basil, nutmeg, and bay leaves

Usage

Commonly used in the fragrance and flavor industry due to its sweet, spicy, and slightly woody scent

Health Concerns

Identified as a potential carcinogen with toxic effects on the liver and potential to cause cancer

Industry Efforts

Efforts are being made to find safer alternatives for its various industrial applications

Downstream Products

• 2565-01-7 nantenine 
• 1207542-48-0 (R)-(-)-nantenine 

Relevant academic research and scientific papers

Evaluation of structural effects on 5-HT2A receptor antagonism by aporphines: Identification of a new aporphine with 5-HT2A antagonist activity

A set of aporphine analogs related to nantenine was evaluated for antagonist activity at 5-HT2A and α1A adrenergic receptors. With regards to 5-HT2A receptor antagonism, a C2 allyl group is detrimental to activity. The chiral center of nantenine is not important for 5-HT2A antagonist activity, however the N6 nitrogen atom is a critical feature for 5-HT2A antagonism. Compound 12b was the most potent 5-HT2A aporphine antagonist identified in this study and has similar potency to previously identified aporphine antagonists 2 and 3. The ring A and N6 modifications examined were detrimental to α1A antagonism. A slight eutomeric preference for the R enantiomer of nantenine was observed in relation to α1A antagonism.

Synthetic studies and pharmacological evaluations on the MDMA ('Ecstasy') antagonist nantenine

The naturally occurring aporphine alkaloid nantenine, has been shown to antagonize behavioral and physiological effects of MDMA in mice. We have synthesized (±)-nantenine via an oxidative cyclization reaction with PIFA and evaluated its binding profile against a panel of CNS targets. To begin to understand the importance of the chiral center of nantenine with regards to its capacity to antagonize the effects of MDMA in vivo, (R)- and (S)-nantenine were prepared and evaluated in a food-reinforced operant task in rats. Pretreatment with either nantenine enantiomer (0.3 mg/kg ip) completely blocked the behavioral suppression induced upon administration of 3.0 mg/kg MDMA. (±)-Nantenine displayed high affinity and selectivity for the α1A adrenergic receptor among several other receptors suggesting that this α1 subtype may be significantly involved in the anti-MDMA effects of the enantiomers.