105579-48-4

Basic information

• Product Name: (8beta,10xi)-6-methyl-8-(1H-tetrazol-1-ylmethyl)ergoline
• CAS NO: 105579-48-4
• Molecular Formula: C₁₇H₂₀N₆
• Molecular Weight: 308.3809
• Mol File: 105579-48-4.mol

Chemical Properties

• Boiling Point: 549.3°C at 760 mmHg
• Flash Point: 286°C
• Density: 1.51g/cm³
• Vapor Pressure: 4.06E-12mmHg at 25°C
• Refractive Index: 1.815
• CAS DataBase Reference: (8beta,10xi)-6-methyl-8-(1H-tetrazol-1-ylmethyl)ergoline(CAS DataBase Reference)
• NIST Chemistry Reference: (8beta,10xi)-6-methyl-8-(1H-tetrazol-1-ylmethyl)ergoline(105579-48-4)
• EPA Substance Registry System: (8beta,10xi)-6-methyl-8-(1H-tetrazol-1-ylmethyl)ergoline(105579-48-4)

Safety Data

• Hazardous Substances Data: 105579-48-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(8beta,10xi)-6-methyl-8-(1H-tetrazol-1-ylmethyl)ergoline is used as a research compound for exploring its potential pharmacological properties and applications in the development of new drugs. Its unique structure and the presence of a tetrazole group make it an interesting candidate for studying its interactions with various biological targets.
Used in Central Nervous System Studies:
As a member of the ergoline alkaloid family, (8beta,10xi)-6-methyl-8-(1H-tetrazol-1-ylmethyl)ergoline is used as a research tool to investigate its effects on the central nervous system. This may lead to a better understanding of its potential therapeutic applications in treating neurological disorders or conditions related to the central nervous system.
Used in Medicinal Chemistry:
(8beta,10xi)-6-methyl-8-(1H-tetrazol-1-ylmethyl)ergoline is used as a starting material or a structural template in the design and synthesis of new compounds with diverse biological activities. Its unique features and the presence of a tetrazole group make it a valuable asset in the field of medicinal chemistry, where it can be used to develop novel therapeutic agents with improved efficacy and selectivity.
Used in Chemical Synthesis:
(8beta,10xi)-6-methyl-8-(1H-tetrazol-1-ylmethyl)ergoline can be used as a synthetic intermediate or a building block in the preparation of other complex organic molecules. Its structural features, including the tetrazole group, can be exploited to synthesize a variety of compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 288-94-8 1H-tetrazole 
• 58752-31-1 6-methyl-8β-tosyloxymethyl-ergoline 
• 18051-16-6 9,10-dihydrolysergol 
• 5878-43-3 9,10-dihydrolysergic acid 
• 3006-19-7 9,10-dihydrolysergic acid methyl ester 
• 288-94-8 2H-tetrazole 
• 96737-35-8 6-methyl-8α-(toluene-4-sulfonyloxymethyl)-ergoline 

Relevant articles and documents

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.

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.

Ergoline derivatives and acid addition salts thereof

Novel ergoline derivatives and acid addition salts thereof are disclosed. These ergoline derivatives possess excellent anti-hypertensive activity, vasodilating activity, anti-ulcer activity, gastric secretion inhibitory activity, brain metabolism improving activity, anti-depressive activity and dopamine-like activity, and, therefore, are useful for prevention and treatment of various diseases such as hypertension, a wide variety of vein disorders, peptic ulcer, brain absormality, depression, Parkinson's disease, high prolactin blood disease, etc.