37686-84-3

Basic information

• Product Name: S(+)-N,N-DIETHYL-N'([8ALPHA]-6-METHYLERGOLIN-8-YL)UREA
• Synonyms: S(+)-N,N-DIETHYL-N'([8ALPHA]-6-METHYLERGOLIN-8-YL)UREA;S(+)-TERGURIDE;S(+)-TERGURIDE (5R, 8S, 10R);R-(+)-TERGURIDE;TRANS-DIHYDROLISURIDE;1-((5r,8s,10r)-6-methyl-8-ergolinyl)-3,3-diethylurea;9,10-alpha-dihydrolisuride;dironyl
• CAS NO: 37686-84-3
• Molecular Formula: C₂₀H₂₈N₄O
• Molecular Weight: 340.46
• EINECS: 253-624-2
• Product Categories: Agonists;Heterocycles;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals
• Mol File: 37686-84-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 203-204° (dec); mp 205-207° (dec) (Cerny)
• Boiling Point: 476.25°C (rough estimate)
• Flash Point: 309.4°C
• Appearance: white/solid
• Density: 1.1056 (rough estimate)
• Vapor Pressure: 8.3E-14mmHg at 25°C
• Refractive Index: 1.6620 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble
• PKA: 13.60±0.20(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.
• CAS DataBase Reference: S(+)-N,N-DIETHYL-N'([8ALPHA]-6-METHYLERGOLIN-8-YL)UREA(CAS DataBase Reference)
• NIST Chemistry Reference: S(+)-N,N-DIETHYL-N'([8ALPHA]-6-METHYLERGOLIN-8-YL)UREA(37686-84-3)
• EPA Substance Registry System: S(+)-N,N-DIETHYL-N'([8ALPHA]-6-METHYLERGOLIN-8-YL)UREA(37686-84-3)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 36/37/39-45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: YS9378700
• Hazardous Substances Data: 37686-84-3(Hazardous Substances Data)

Usage

Description

S(+)-N,N-DIETHYL-N'([8ALPHA]-6-METHYLERGOLIN-8-YL)UREA, also known as Terguride, is a semi-synthetic ergoline derivative that functions as a partial dopamine D2 agonist and 5HT2B/2C receptor antagonist. It exhibits antiparkinsonian effects in MPTP-treated cynomolgus monkeys and has the ability to act as a partial agonist at the recruitment of β-arrestin2 to the D2 receptor. Additionally, Terguride has been found to ameliorate monocrotaline-induced pulmonary hypertension in rats.
Used in Pharmaceutical Industry:
S(+)-N,N-DIETHYL-N'([8ALPHA]-6-METHYLERGOLIN-8-YL)UREA is used as an anti-hyperprolactinemia agent for the treatment of conditions related to excessive prolactin levels in the body. Its mechanism of action involves the partial agonism of dopamine D2 receptors, which helps regulate prolactin secretion.

References

1) Akai et al. (1993), Effects of terguride, a partial D2 agonist, on MPTP-lesioned parkinsonian cynomolgus monkeys; Ann. Neurol., 133 507 2) Klewe et al. (2008), Recruitment of beta-arrestin2 to the dopamine D2 receptor: insights into anti-psychotic and anti-parkinsonian drug receptor signaling; Neuropharmacology, 54 1215 3) Dumitrascu et al. (2011), Terguride ameliorates monocrotaline-induced pulmonary hypertension in rats; Eur. Respir. J., 37 1104

InChI:InChI=1/C20H28N4O/c1-4-24(5-2)20(25)22-14-10-16-15-7-6-8-17-19(15)13(11-21-17)9-18(16)23(3)12-14/h6-8,11,14,16,18,21H,4-5,9-10,12H2,1-3H3,(H,22,25)/t14-,16+,18+/m0/s1

Upstream product

• 96860-91-2 1-<(5R,8S,10R)-6-cyano-8-ergolinyl>-3,3-diethylurea 
• 18016-80-3 lisuride 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 59043-22-0 8alpha-Amino-6-methylergoline 
• 106347-60-8 1-<(5R,8S,10R)-6-methyl-8-ergolinyl>-3,3-diethylurea dihydrogen citrate 

Downstream Products

• 178443-53-3 8α-[[2-(benzoylsulfanyl)acetyl]amino]-6-methylergoline 
• 178476-60-3 8α-[[2-(benzoylsulfanyl)propionyl]amino]-6-methylergoline 
• 77650-95-4 1-<(5R,8S,10R)-6-propyl-8-ergolinyl>-3,3-diethylurea 
• 122888-36-2 (6aR,9S,10aR)-9-(3,3-Diethyl-ureido)-7-methyl-6,6a,7,8,9,10-hexahydro-4H-indolo[4,3-fg]quinoline-10a-carboxylic acid phenylamide 
• 122888-33-9 (6aR,9S,10aR)-4-(tert-Butyl-dimethyl-silanyl)-9-(3,3-diethyl-ureido)-7-methyl-6,6a,7,8,9,10-hexahydro-4H-indolo[4,3-fg]quinoline-10a-carboxylic acid phenylamide 

Relevant articles and documents

Molecular structure of cis- and trans-tergurides

Four isomers of terguride, a semisynthetic ergot alkaloid derivative, have been prepared by catalytic hydrogenation of (5R.8S)- and (5S,8S)-lisuride [1,1-diethyl-3-(6-methyl-8-ergolenyl)urea]. Relative stereochemistry of the isomers is based on NMR and CD spectra. Absolute configuration of all the series has been confirmed by the X-ray crystal structure determination of (5R,8S,10S)-terguride 2-bromobenzoate [1,1-diethyl-3-(6-methyl-8-isoergolenyl)urea, cis-dihydrolisuride].

Process for the production ergoline derivatives

Ergoline derivatives of general Formula I STR1 wherein C8 C9 and C9 C10 are both CC-single bonds or one is a C=C-double bond, R6 is C1-4 alkyl, R8 is methyl, hydroxymethyl, carbonylmethoxy, ureido or N,N-diethylureido, each in the α- or β-position, and R is hydrogen or nitro, are prepared by dehydrogenation of corresponding 2,3-dihydroergoline derivatives using an electrophilic reagent in an apolar solvent and a base.

SOLVOLYSIS OF SOME 1-(8α-ERGOLINYL)-3,3-DIETHYLUREAS AND THEIR SALTS

Nine salts of 1-(8α-ergolinyl)-3,3-diethylurea (II) were prepared and their solubility in water and the stability of the aqueous solutions at 60 and 100 deg C were studied.The main product of hydrolysis is 6-methyl-8α-aminoergoline IV.The urethan VII is formed in the ethanolic solution.Both decomposition products are also formed under long-term storage at +5 deg C.The course of hydrolysis of N-propyl homologue III is similar.The decomposition of 9,10-didehydro derivative I is much slower under the conditions used.