162070-34-0

Usage

Uses

Used in Pharmaceutical Applications:
(5R,8S,10R)-2-Chloro-6-methyl-8-(1H-imidazol-1-ylmethyl)ergoline is used as a potential therapeutic agent for the treatment of neurological and psychiatric disorders. Its unique structure and pharmacological properties make it a candidate for developing novel treatments targeting various conditions.
Used in Research and Development:
In the field of neuroscience, (5R,8S,10R)-2-Chloro-6-methyl-8-(1H-imidazol-1-ylmethyl)ergoline serves as a valuable research tool. It can be utilized to study the mechanisms underlying neurological and psychiatric disorders, as well as to investigate the effects of ergoline derivatives on the central nervous system.
Used in Drug Synthesis:
As a derivative of ergoline, (5R,8S,10R)-2-Chloro-6-methyl-8-(1H-imidazol-1-ylmethyl)ergoline may also be used in the synthesis of other psychedelic drugs and compounds with potential therapeutic applications. Its unique structural features can be exploited to create new molecules with specific pharmacological profiles.
Used in Chemical and Pharmaceutical Industries:
(5R,8S,10R)-2-Chloro-6-methyl-8-(1H-imidazol-1-ylmethyl)ergoline is used as a key intermediate in the synthesis of various pharmaceutical products, particularly those targeting neurological and psychiatric disorders. Its unique properties make it a valuable component in the development of novel drugs with improved efficacy and safety profiles.

InChI:InChI=1/C19H21ClN4/c1-23-9-12(10-24-6-5-21-11-24)7-14-13-3-2-4-16-18(13)15(8-17(14)23)19(20)22-16/h2-6,11-12,14,17,22H,7-10H2,1H3/t12-,14?,17+/m0/s1

Upstream product

• 288-32-4 1H-imidazole 
• 74627-27-3 (5R,8R,10R)-2-chloro-6-methyl-8-ergolinylmethyl p-toluenesulfonate 
• 162070-44-2 Toluene-4-sulfonic acid (6aR,9S,10aR)-5-chloro-7-methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester 
• 3006-19-7 9,10-dihydrolysergic acid methyl ester 
• 5878-43-3 9,10-dihydrolysergic acid 
• 66835-16-3 ((6aR,9R,10aR)-5-Chloro-7-methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-yl)-methanol 
• 110883-13-1 methyl (5R,8R,10R)-2-chloro-6-methyl-8-ergolinecarboxylate 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of new (5R,8S,10R)-ergoline derivatives with antihypertensive of dopaminergic activity

A series of new (5R,8S,10R)-ergoline derivatives was synthesized, and their antihypertensive and dopaminergic activities were evaluated in conscious spontaneously hypertensive rats and in rats with unilateral 6-hydroxydopamine-induced lesions of the substantia nigra, respectively. (5R,8S,10R)-6-Methyl-8-ergolinemethanols, prepared from the corresponding ergolinecarboxylates, were converted to the tosylates, which were treated with various five-membered heterocycles containing nitrogen atoms to afford the new ergolines. (5R,8S,10R)-8-(1-Imidazolylmethyl)-6-methylergoline (5a, BAM-2101) and (5R,8S,10R)-2-bromo-6-methyl-8-(1,2,4-triazol-1-ylmethyl)ergoline (7c, BAM-2202) exhibited potent antihypertensive activities. The maximum falls of systolic blood presure after oral administration of 5a and 7c at 3 mg/kg were 95 and 132 mmHg, respectively, while those of cianergoline, bromocriptine mesylate, hydralazine, and nifedipine at the same dose were 40, 37, 47, and 49 mmHg, respectively. The durations of significant antihypertensive effects of these compounds except nifedipine were more than 7 h. None of the ergolines exhibited potent dopaminergic activity. Structure-activity relationships are discussed.

Synthesis and structure-activity relationships of new (5R,8R,10R)-ergoline derivatives with antihypertensive or dopaminergic activity

A series of new (5R,8R,10R)-ergoline derivatives was synthesized, and their antihypertensive and dopaminergic activities were tested in conscious spontaneously hypertensive rats and in rats with unilateral 6- hydroxydopamine-induced lesions of the substantia nigra. (5R,8R,10R)-6- Alkyl-8-ergolinemethanols, prepared from the corresponding ergolinecarboxylates, were converted to the tosylates, which were treated with various five-membered heterocycles containing nitrogen atoms to afford the new ergolines. (5R,8R,10R)-8-(1,2,4-Triazol-1-ylmethyl)-6-methylergoline (4s, maleate: BAM-1110) exhibited potent dopaminergic activity, about 18- fold greater than that of bromocriptine mesylate. (5R,8R,10R)-8-(1,2,4- Triazol-1-ylmethyl)-6-propylergoline (8b, fumarate: BAM-1602) showed extremely potent dopaminergic activity, being about 220 and 1.15 times more active than bromocriptine mesylate and pergolide mesylate, respectively. Several compounds exhibited potent antihypertensive activity. Structure- activity relationships for antihypertensive and dopaminergic activities are discussed.