1-[(3,4-dimethoxyphenyl)methyl]-2-[3-({5-[(3-{1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium-2-yl}propanoyl)oxy]pentyl}oxy)-3-oxopropyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium dibenzenesulfonate

• ChemBase ID: 73279
• Molecular Formular: C65H82N2O18S2
• Molecular Mass: 1243.47918
• Monoisotopic Mass: 1242.50040579
• SMILES: c1(c(cc2c(c1)CC[N+](C2Cc1ccc(c(c1)OC)OC)(CCC(=O)OCCCCCOC(=O)CC[N+]1(C(c2cc(c(cc2CC1)OC)OC)Cc1ccc(c(c1)OC)OC)C)C)OC)OC.c1ccccc1S(=O)(=O)[O-].c1ccccc1S(=O)(=O)[O-]
• Canonical SMILES: [O-]S(=O)(=O)c1ccccc1.[O-]S(=O)(=O)c1ccccc1.COc1cc2c(cc1OC)CC[N+](C2Cc1ccc(c(c1)OC)OC)(C)CCC(=O)OCCCCCOC(=O)CC[N+]1(C)CCc2c(C1Cc1ccc(c(c1)OC)OC)cc(c(c2)OC)OC
• InChI: InChI=1S/C53H72N2O12.2C6H6O3S/c1-54(22-18-38-32-48(62-7)50(64-9)34-40(38)42(54)28-36-14-16-44(58-3)46(30-36)60-5)24-20-52(56)66-26-12-11-13-27-67-53(57)21-25-55(2)23-19-39-33-49(63-8)51(65-10)35-41(39)43(55)29-37-15-17-45(59-4)47(31-37)61-6;2*7-10(8,9)6-4-2-1-3-5-6/h14-17,30-35,42-43H,11-13,18-29H2,1-10H3;2*1-5H,(H,7,8,9)/q+2;;/p-2
• InChIKey: XXZSQOVSEBAPGS-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(3,4-dimethoxyphenyl)methyl]-2-[3-({5-[(3-{1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium-2-yl}propanoyl)oxy]pentyl}oxy)-3-oxopropyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium dibenzenesulfonate
• IUPAC Traditional name: atracurium dibenzenesulfonate
• Synonyms: Atracurium besylate; 2,2'-[1,5-Pentanediylbis[oxy(3-oxo-3,1-propanediyl)]]bis[1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinolinium Benzenesulfonate; Atracurium Dibesylate; BW 33A; Tracur; Wellcome 33A74; 2,2′-[1,5-Pentanediylbis[oxy(3-oxo-3,1-propanediyl)]]bis[1-[3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinolinium]dibenzenesulfonate; BW-33A; Tracrium; Atracurium besylate

Database IDs

• CAS Number: 64228-81-5
• EC Number: 264-743-4
• MDL Number: MFCD00797403
• PubChem SID: 162038199; 24724397
• PubChem CID: 47320

CALCULATED PROPERTIES

• Acid pKa: 19.016506
• H Acceptors: 10
• H Donor: 0
• LogD (pH = 5.5): -0.95903206
• LogD (pH = 7.4): -0.95903206
• Log P: -0.95903206
• Molar Refractivity: 280.6772 cm^3
• Polarizability: 100.60693 Å^3
• Polar Surface Area: 126.44 Å^2
• Rotatable Bonds: 28
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: ~27 mg/mL
• Apperance: white powder; White to Off-White Solid
• Melting Point: 85-90°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: besylate
• Empirical Formula (Hill Notation): C65H82N2O18S2

DETAILS

Selleck Chemicals - S1832

Research Area: Neurological Disease
Biological Activity:

Sigma Aldrich - A7604

Biochem/physiol Actions
Nicotinic acetylcholine receptor antagonist.

Toronto Research Chemicals - A794500

A neuromuscular blocking agent.

REFERENCES

• Hughes, R., et al.: Br. J. Anaesth., 53, 31 (1981)
• Basta, S.J., et al.: Anesth. Analog., 61, 723 (1981)
• Neill, E.A., et al.: Xenobiotica, 12, 203 (1981)