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

Terguride (37686-84-3) is a semi-synthetic ergoline derivative which acts as a partial dopamine D2 agonist and 5HT2B/2C receptor antagonist. Displays antiparkinsonian effects in MPTP-treated cynomolgus monkeys.1?Partial agonist at recruitment of β-arrestin2 to the D2 receptor.2 Terguride ameliorates monocrotaline-induced pulmonary hypertension in rats.3

Uses

An ergot alkaloid derivative that acts as a partial dopamine D2-receptor agonist. An anti-hyperprolactinemia agent.

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

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

Downstream Products

• 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 
• 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 
• 178476-60-3 8α-[[2-(benzoylsulfanyl)propionyl]amino]-6-methylergoline 
• 178443-53-3 8α-[[2-(benzoylsulfanyl)acetyl]amino]-6-methylergoline 
• 77650-95-4 1-<(5R,8S,10R)-6-propyl-8-ergolinyl>-3,3-diethylurea 

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.

Method for treatment of endometritis in mammalian females

This invention relates to a method for the treatment of endometritis (chronic and/or acute puerperal inflammations) in mammalian females comprising the administration of 1-(8-alpha-ergolinyl)-3,3-diethylurea derivatives of Formula I STR1 in which R1 represents an alkyl group containing 1 to 3 carbon atoms, R2 represents a hydrogen atom or an alkyl group containing 1 to 3 carbon atoms, and X represents a hydrogen atom or a double bond between the carbon atoms at positions 9 and 10. The compound according to Formula I, or a pharmaceutically acceptable acid addition salt thereof, is the physiologically active component of the therapeutic composition and method. The compound may be combined with a pharmaceutically acceptable diluent, vehicle, excipient, auxiliary, or carrier. The invention is particularly advantageous in veterinary medicine, when applied to the treatment of farm animals, such a cows.