138625-85-1

Basic information

• Product Name: 1H-1,4-Diazepine-6-methanol, hexahydro-1-methyl-4-(phenylmethyl)-
• CAS NO: 138625-85-1
• Molecular Formula: C14H22N2O
• Molecular Weight: 234.341
• Mol File: 138625-85-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1H-1,4-Diazepine-6-methanol, hexahydro-1-methyl-4-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-1,4-Diazepine-6-methanol, hexahydro-1-methyl-4-(phenylmethyl)-(138625-85-1)
• EPA Substance Registry System: 1H-1,4-Diazepine-6-methanol, hexahydro-1-methyl-4-(phenylmethyl)-(138625-85-1)

Safety Data

• Hazardous Substances Data: 138625-85-1(Hazardous Substances Data)

Usage

Class of compound

Benzodiazepines

Derivative of

Diazepam (Valium)

Properties

Sedative, anxiolytic, muscle relaxant

Mechanism of action

Enhances the effects of gamma-aminobutyric acid (GABA) in the central nervous system

Uses

Treatment of anxiety, insomnia, and as a premedication prior to surgical procedures

Administration

Orally or intravenously under medical supervision

Precautions

Potential for abuse and dependence

Upstream product

• 166047-27-4 1-benzyl-4-methylhexahydro-1H-1,4-diazepine-6-carboxylic acid 
• 56904-09-7 N-methyl-2-(benzylamino)ethylamine 
• 138625-84-0 methyl 1-benzyl-4-methylhexahydro-1H-1,4-diazepine-6-carboxylate 

Downstream Products

• 173599-95-6 (1-benzyl-4-methylhexahydro-1H-1,4-diazepin-6-yl)acetonitrile 
• 173599-96-7 6-(2-aminoethyl)-1-benzyl-4-methylhexahydro-1H-1,4-diazepine 
• 173599-94-5 6-aminomethyl-1-benzyl-4-methylhexahydro-1H-1,4-diazepine 
• 138625-86-2 6-chloromethyl-1-benzyl-4-methylhexahydro-1H-1,4-diazepine 
• 173599-93-4 N-<(1-benzyl-4-methylhexahydro-1H-1,4-diazepin-6-yl)methyl>phthalimide 

Relevant articles and documents

Development of potent serotonin-3 (5-HT3) receptor antagonists. II. Structure-activity relationships of N-(1-benzyl-4-methylhexahydro-1H-1,4- diazepin-6-yl)carboxamides

Our studies on 4-amino-5-chloro-2-ethoxybenzamides led to the discovery that the N-(1,4-dimethylhexahydro-1H-1,4-diazepin-6-yl)benzamide 9 and the 1- benzyl-4-methylhexahydro-1H-1,4-diazepine analogue 10 are potent serotonin-3 (5-HT3) receptor antagonists. Structure-activity relationship (SAR) studies on the influence of the aromatic nucleus of 9 and 10 upon inhibition of the von Bezold-Jarisch reflex in rats are described. Heteroaromatic rings such as pyrrole, thiophene, furan, pyridine, pyridaziae, 1,2-benzisoxazole, indole, quinoline, and isoquinoline rings showed weak 5-HT3 receptor antagonistic activity. Within this series, use of the 1H-indazole ring as an aromatic moiety led to a substantial increase of the activity; the 1H- indazolylcarboxamides 54, 57, 97, and 102 showed potent 5-HT3 receptor antagonistic activity. The optimal compound identified via extensive SAR studies was N-(1-benzyl-4-methylhexahydro-1H-1,4-diazepin-6-yl)-1H-indazole- 3-carboxamide (54), whose effect was superior to that of the corresponding benzamide 10 and essentially equipotent to those of ondansetron (1) and granisetron (4).