(2R,4R,7R)-4-[(methylsulfanyl)methyl]-6-propyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),9,12(16),13-tetraene; methanesulfonic acid

• ChemBase ID: 134052
• Molecular Formular: C20H30N2O3S2
• Molecular Mass: 410.5938
• Monoisotopic Mass: 410.16978483
• SMILES: CCCN1C[C@@H](C[C@H]2[C@H]1Cc1c[nH]c3c1c2ccc3)CSC.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.CCCN1C[C@H](CSC)C[C@H]2[C@H]1Cc1c[nH]c3c1c2ccc3
• InChI: InChI=1S/C19H26N2S.CH4O3S/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;1-5(2,3)4/h4-6,10,13,16,18,20H,3,7-9,11-12H2,1-2H3;1H3,(H,2,3,4)/t13-,16-,18-;/m1./s1
• InChIKey: UWCVGPLTGZWHGS-ZORIOUSZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,7R)-4-[(methylsulfanyl)methyl]-6-propyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),9,12(16),13-tetraene; methanesulfonic acid; (2R,4R,7R)-4-[(methylsulfanyl)methyl]-6-propyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraene; methanesulfonic acid
• IUPAC Traditional name: (2R,4R,7R)-4-[(methylsulfanyl)methyl]-6-propyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),9,12(16),13-tetraene; methanesulfonic acid; (2R,4R,7R)-4-[(methylsulfanyl)methyl]-6-propyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraene; methanesulfonic acid
• Synonyms: 8β-[(Methylthio)methyl]-6-propylergoline methanesulfonate salt; Pergolide methanesulfonate salt; Pergolide mesylate salt; Pergolida; Pergolidum; Permax; Pergotoliderived; Pergolide mesylate

Database IDs

• CAS Number: 66104-22-1; 66104-23-2
• MDL Number: MFCD00153859
• PubChem SID: 162228329; 24277927
• PubChem CID: 47812

CALCULATED PROPERTIES

• Acid pKa: 17.350344
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 0.84682393
• LogD (pH = 7.4): 2.1517017
• Log P: 4.22529
• Molar Refractivity: 97.0167 cm^3
• Polarizability: 38.847607 Å^3
• Polar Surface Area: 19.03 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble5.2 mg/mL; ethanol: soluble2 mg/mL; H2O: insoluble
• Apperance: white solid
• Optical Rotation: [α]20/D -35°, c = 0.2 in pyridine(lit.)

Safety Information

• RTECS: KE6345000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 2
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)
• Mechanism of Action: Agonist at the dopamine D2, D1 and serotonin 5-HT(1A), 5-HT(1B), 5-HT(2A), 5-HT(2B), and 5-HT(2C) receptors

Product Information

• Purity: ≥98%
• Salt Data: Mesylate
• Application(s): Also used for veterinary purposes.; Used to treat various conditions including Parkinson's disease, hyperprolactinemia, and restless leg syndrome.

DETAILS

Sigma Aldrich - P8828

Biochem/physiol Actions
Dopaminergic agonist; suppresses pituitary secretion of prolactin; anti-Parkinsonian agent.

REFERENCES

• Lemberger, L. et al., Science (Washington, D.C.), 1979
• Rubin, A. et al., Clin. Pharmacol. Ther. (St. Louis), 1981