(7R)-10-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide; methanesulfonic acid

• ChemBase ID: 133025
• Molecular Formular: C33H44BrN5O8S
• Molecular Mass: 750.70016
• Monoisotopic Mass: 749.20939639
• SMILES: CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(N1C(=O)[C@](O2)(C(C)C)NC(=O)C1CN([C@@H]2Cc3c4c(cccc4[nH]c3Br)C2=C1)C)O.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.CC(C[C@H]1C(=O)N2CCC[C@H]2[C@]2(N1C(=O)[C@@](O2)(NC(=O)C1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c([nH]3)Br)C(C)C)O)C
• InChI: InChI=1S/C32H40BrN5O5.CH4O3S/c1-16(2)12-24-29(40)37-11-7-10-25(37)32(42)38(24)30(41)31(43-32,17(3)4)35-28(39)18-13-20-19-8-6-9-22-26(19)21(27(33)34-22)14-23(20)36(5)15-18;1-5(2,3)4/h6,8-9,13,16-18,23-25,34,42H,7,10-12,14-15H2,1-5H3,(H,35,39);1H3,(H,2,3,4)/t18?,23-,24+,25+,31-,32+;/m1./s1
• InChIKey: NOJMTMIRQRDZMT-NEKRQHSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7R)-10-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0^2,^6]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide; methanesulfonic acid
• IUPAC Traditional name: (7R)-10-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^2,^6]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide; methanesulfonic acid
• Synonyms: (+)-2-Bromo-12′-hydroxy-2′-(1-methylethyl)-5′-(2-methylpropyl)ergotaman-3′,6′-18-trione methanesulfonate salt; (+)-Bromocriptine methanesulfonate salt; Bromocriptine mesylate salt; 2-Bromo-α-ergocryptine methanesulfonate salt

Database IDs

• CAS Number: 22260-51-1
• EC Number: 244-881-1
• MDL Number: MFCD00069218
• Beilstein Number: 4115238
• PubChem SID: 162227302; 24277885
• PubChem CID: 16219016

CALCULATED PROPERTIES

• Acid pKa: 9.677615
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.6492515
• LogD (pH = 7.4): 3.8034801
• Log P: 3.8871677
• Molar Refractivity: 165.5124 cm^3
• Polarizability: 65.108116 Å^3
• Polar Surface Area: 118.21 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: soluble23 mg/mL; H2O: soluble0.8 mg/mL
• Apperance: white solid
• Optical Rotation: [α]20/D +95°, c = 1 in methanol: methylene chloride (1:1)(lit.)

Safety Information

• RTECS: KE1595000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... DRD2(1813), DRD3(1814), PRL(5617)

DETAILS

Sigma Aldrich - B2134

Biochem/physiol Actions
Agonist at D2 and D3 dopamine receptors; inhibits prolactin secretion.