3524-20-7

Usage

Chemical class

pyrazole

Structure

pyrazole ring with an amino group at position 5 and a pentyl group attached at position 1

Type of compound

synthetic cannabinoid

Receptors

acts as a potent agonist at the CB1 and CB2 receptors

Identification

identified as an ingredient in synthetic cannabis products

Adverse effects

range of adverse effects, including agitation, hallucinations, and even fatalities

Classification

classified as a controlled substance in many countries.

Upstream product

• 110-62-3 pentanal 
• 353-07-1 3-hydrazinylpropanenitrile 
• 89158-20-3 3-[N'-Pent-(E)-ylidene-hydrazino]-propionitrile 

Downstream Products

• 103586-29-4 4-amino-7-oxo-1-pentyl-N-2-propenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide 
• 89865-49-6 benzylic ester of 4-Amino-6-methyl-1-pentyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid 
• 122359-11-9 4-Amino-1-pentyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid phenylamide 
• 103585-88-2 4-Amino-1-pentyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid benzylamide 
• 122359-16-4 4-Amino-6-methyl-1-pentyl-1H-pyrazolo[3,4-b]pyridine-5-carbonyl chloride 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of a series of anxioselective pyrazolopyridine ester and amide anxiolytic agents

A series of 1-substituted 4-amino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid esters and amides were synthesized and screened for anxiolytic activity in the shock-induced suppression of drinking (SSD) test. The compounds were also tested for their ability to displace [3H]flunitrazepam (FLU) from brain benzodiazepine (BZ) binding sites. Many compounds were active in these screens and, additionally, demonstrated a selectivity for the type 1 BZ (BZ1) receptor over the type 2 BZ (BZ2) receptor as indicated by Hill coefficients significantly less than unity and analysis of [3H]FLU binding results from different brain regions. Based on the results of structure-activity studies of these compounds, a hypothesis was proposed to explain the structural features necessary for optimal interaction with brain BZ receptors. A detailed pharmacological evaluation of one of the most potent behaviorally active compounds (27) demonstrated it to be BZ1 selective; also, in comparison to diazepam, 27 showed minimal sedative and alcohol interactive properties at therapeutically effective doses.

Process for preparing pyrazolopyridine compounds

Compounds of the formula (I): STR1 wherein R4 is hydrogen, D is oxygen or NR6, R1, R3, R6, R7 and R8 have defined values, and n is 1 or 2 are produced by internally cyclizing a compound of the formula (XV): STR2 wherein R19 is a value of R1 or hydrogen and, if R19 is hydrogen, reacting the cyclization product with R1 --Br and a weak base such as potassium carbonate.

Pyrazolo[3,4-b]pyridine carboxylic acid esters and their pharmaceutical use

Compounds of the formula (I): STR1 wherein R1, R3, R4, R5 and R6 have defined values and the N-oxides at the 7-position of the pyrazolo[3,4-b]pyridine ring system and the pharmaceutically-acceptable acid-addition salts thereof, processes for their preparation and use, pharmaceutical compositions, and intermediates for preparing said compounds of the formula (I). The compounds of formula (I) are central nervous system depressants, for example anxiolytic agents.

CNS-Depressant pyrazolopyridines

Compounds of the formula (I): STR1 wherein R1, R3, R4, R7 and R8 are as described herein, D is oxygen or NR6, n is 1 or 2 and the physiologically acceptable salts thereof useful in reducing anxiety in an animal such as man. The compounds are potent anxiolytics having reduced side effects compared to known anxiolytics. Also pharmaceutical compositions, intermediates and methods of treatment and synthesis are described.