(1S,16R)-9,21-dihydroxy-10,25-dimethoxy-15,15,30-trimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.118,22.027,31.016,34]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaen-15-ium pentahydrate chloride hydrochloride

• ChemBase ID: 136824
• Molecular Formular: C37H52Cl2N2O11
• Molecular Mass: 771.72158
• Monoisotopic Mass: 770.29481585
• SMILES: CN1CCc2cc(c3cc2[C@@H]1Cc1ccc(cc1)Oc1c2c(cc(c1O)OC)CC[N+]([C@@H]2Cc1ccc(c(c1)O3)O)(C)C)OC.O.O.O.O.O.Cl.[Cl-]
• Canonical SMILES: COc1cc2CCN([C@@H]3c2cc1Oc1cc(ccc1O)C[C@@H]1c2c(CC[N+]1(C)C)cc(c(c2Oc1ccc(C3)cc1)O)OC)C.O.O.O.O.O.Cl.[Cl-]
• InChI: InChI=1S/C37H40N2O6.2ClH.5H2O/c1-38-14-12-24-19-32(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-37-35-25(20-34(43-5)36(37)41)13-15-39(2,3)29(35)17-23-8-11-30(40)31(18-23)45-33;;;;;;;/h6-11,18-21,28-29H,12-17H2,1-5H3,(H-,40,41);2*1H;5*1H2/t28-,29+;;;;;;;/m0......./s1
• InChIKey: WMIZITXEJNQAQK-GGDSLZADSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,16R)-9,21-dihydroxy-10,25-dimethoxy-15,15,30-trimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^3,^6.1^8,^1^2.1^1^8,^2^2.0^2^7,^3^1.0^1^6,^3^4]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaen-15-ium pentahydrate chloride hydrochloride
• IUPAC Traditional name: (1S,16R)-9,21-dihydroxy-10,25-dimethoxy-15,15,30-trimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^3,^6.1^8,^1^2.1^1^8,^2^2.0^2^7,^3^1.0^1^6,^3^4]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaen-15-ium pentahydrate chloride hydrochloride
• Synonyms: (+)-Tubocurarine chloride pentahydrate; (+)-Tubocurarine hydrochloride; Tubocurarine hydrochloride pentahydrate

Database IDs

• CAS Number: 6989-98-6
• MDL Number: MFCD00150157
• Beilstein Number: 3896374
• PubChem SID: 24889925; 24900034; 24859074; 162231092
• PubChem CID: 23422

CALCULATED PROPERTIES

• Acid pKa: 8.585149
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.65644765
• LogD (pH = 7.4): 2.2013767
• Log P: 3.144135
• Molar Refractivity: 187.0636 cm^3
• Polarizability: 67.55122 Å^3
• Polar Surface Area: 80.62 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 275-280 °C (dec.)(lit.)
• Optical Rotation: [α]19/D +190°, c = 0.5 in H2O; [α]20/D +195±5°, c = 0.5% in H2O

Safety Information

• RTECS: YO5100000
• European Hazard Symbols: Toxic (T)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; 3
• Risk Statements: 25
• Safety Statements: 22-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 2; UN 1544 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97%; ≥97.0% (TLC); 97%
• Impurities: ~12% water
• Empirical Formula (Hill Notation): C37H41ClN2O6 · HCl · 5H2O; C37H42Cl2N2O6 · 5H2O

DETAILS

Sigma Aldrich - T2379

Biochem/physiol Actions
Muscle relaxant; nicotinic acetylcholine receptor antagonist; can induce neuromuscular paralysis.

Sigma Aldrich - 93750

Biochem/physiol Actions
Classical competitive antagonist of the nicotinic acetylcholine receptor1. Structure-activity relationships and conformational studies for tubocurarine binding at the nicotinic AChR.2
Packaging
1 g in poly tube
250 mg in poly bottle

Sigma Aldrich - 317330

Packaging
100 mg in glass bottle