Home > Name List By other > (6aR,9R,10aR)-9-(methylsulfanylmethyl)-7-propyl-6,6a,8,9,10, 10a-hexahydro-4H-indolo[4,3-fg]quinoline

CAS No 66104-22-1 , (6aR,9R,10aR)-9-(methylsulfanylmethyl)-7-propyl-6,6a,8,9,10,
10a-hexahydro-4H-indolo[4,3-fg]quinoline

  • Name: (6aR,9R,10aR)-9-(methylsulfanylmethyl)-7-propyl-6,6a,8,9,10,
    10a-hexahydro-4H-indolo[4,3-fg]quinoline
  • Synonyms: Pergolide (INN);Permax; 66104-22-1;(6aR,9R,10aR)-9-(methylsulfanylmethyl)-7-propyl-6,6a,8,9,10,
    10a-hexahydro-4H-indolo[4,3-fg]quinoline; Pergolidum [INN-Latin]; Pergolidum; Pergolida; Permax (TN); Pergolida [INN-Spanish];
  • CAS Registry Number:
  • Melting Point: 207.5 ºC
  • Flash Point: 491.3 °C at 760 mmHg
  • Boiling Point: 491.3 °C at 760 mmHg
  • Density: 1.124 g/cm3
  • Flash Point: 491.3 °C at 760 mmHg
  • Molecular Weight: 314.48814
  • InchiKey: YEHCICAEULNIGD-MZMPZRCHSA-N
  • InChI: InChI=1S/C19H26N2S/c1-3-7-21-11-13(12-22-2)8-16-15-5-4-6-17-19(15)14(10-
    20-17)9-18(16)21/h4-6,10,13,16,18,20H,3,7-9,11-12H2,1-2H3/t13-,16-,
    18-/m1/s1
  • Molecular Formula: C19H26N2S
  • Molecular Structure:CAS No:66104-22-1 (6aR,9R,10aR)-9-(methylsulfanylmethyl)-7-propyl-6,6a,8,9,10,<br />10a-hexahydro-4H-indolo[4,3-fg]quinoline

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References of (6aR,9R,10aR)-9-(methylsulfanylmethyl)-7-propyl-6,6a,8,9,10,
10a-hexahydro-4H-indolo[4,3-fg]quinoline
Title: Pergolide
CAS Registry Number: 66104-22-1
CAS Name: (8b)-8-[(Methylthio)methyl]-6-propylergoline
Synonyms: D-6-n-propyl-8b-methylmercaptomethylergoline
Manufacturers' Codes: LY-141B
Molecular Formula: C19H26N2S
Molecular Weight: 314.49
Percent Composition: C 72.56%, H 8.33%, N 8.91%, S 10.20%
Literature References: D1/D2 dopaminergic agonist that also decreases plasma prolactin concentrations. Prepn: E. C. Kornfeld, N. J. Bach, US 4166182 (1979 to Lilly). Industrial synthesis: W. Cabri et al., Org. Process Res. Dev. 10, 198 (2006). Dopaminergic effects in rats: R. W. Fuller et al., Life Sci. 24, 375 (1979); T. T. Yen et al., ibid. 25, 209 (1979). Clinical pharmacology: L. Lemberger, R. E. Crabtree, Science 205, 1151 (1979). Pharmacological evaluation as antiparkinson agent: W. C. Koller, Neuropharmacology 19, 831 (1980). Clinical study in galactorrhea: J. T. Callaghan et al., Life Sci. 28, 95 (1981); in hyperprolactinemia: S. Francks et al., Lancet 2, 659 (1981); in treatment of pituitary tumors secreting prolactin or growth hormone: D. L. Kleinberg et al., N. Engl. J. Med. 309, 704 (1983). Clinical studies in Parkinson's disease: J. Jankovic, J. Orman, Adv. Neurol. 45, 551 (1986); C. W. Olanow, M. J. Alberts, ibid. 555; in restless legs syndrome: C. Trenkwalder et al., Neurology 62, 1391 (2004). Comprehensive description: D. J. Sprankle, E. C. Jensen, Anal. Profiles Drug Subs. Excip. 21, 375-413 (1992). Review of clinical experience in Parkinson's disease: U. Bonuccelli et al., Clin. Neuropharmacol. 25, 1-10 (2002).
Properties: Solid, mp 217.5°.
Melting point: mp 217.5°
 
Derivative Type: Mesylate
CAS Registry Number: 66104-23-2
Manufacturers' Codes: LY-127809
Trademarks: Celance (Lilly); Permax (Lilly); Nopar (Lilly)
Molecular Formula: C19H26N2S.CH3SO3H
Molecular Weight: 410.59
Percent Composition: C 58.50%, H 7.36%, N 6.82%, S 15.62%, O 11.69%
Properties: Crystals, mp 258-260° (dec) (Sprankle, Jensen); also reported as mp 267.4° (Cabri). uv max (water): 279 nm (e 6385); (methanol): 280 nm (e 6980); (dehydrated ethanol): 281 nm (e 6993). aD20 between -18.0° and -23.0° (c = 10 mg/ml in DMF). pKa (66% DMF) 7.8. Sparingly sol in DMF, methanol; slightly sol in water, 0.01N HCl, chloroform, acetonitrile, dichloromethane, dehydrated ethanol; very slightly sol in acetone. Practically insol in 0.1N NaOH, 0.1N HCl, ether. Partition coefficient at 25° (chloroform/water): 6.14 (pH 2.19); 119.6 (pH 4.02).
Melting point: mp 258-260° (dec) (Sprankle, Jensen); mp 267.4° (Cabri)
pKa: pKa (66% DMF) 7.8
Optical Rotation: aD20 between -18.0° and -23.0° (c = 10 mg/ml in DMF)
Log P: Partition coefficient at 25° (chloroform/water): 6.14 (pH 2.19); 119.6 (pH 4.02)
Absorption maximum: uv max (water): 279 nm (e 6385); (methanol): 280 nm (e 6980); (dehydrated ethanol): 281 nm (e 6993)
 
Therap-Cat: Antiparkinsonian.
Keywords: Antiparkinsonian; Dopamine Receptor Agonist.