CAS 57-95-4

(+)-Tubocurarine

Description:

(+)-Tubocurarine is a naturally occurring alkaloid derived from the bark of certain South American plants, notably Chondrodendron tomentosum. It is primarily known for its use as a neuromuscular blocking agent in anesthesia. This compound acts as a competitive antagonist at the neuromuscular junction, specifically blocking the action of acetylcholine at nicotinic receptors on the motor end plate, leading to muscle paralysis. (+)-Tubocurarine is characterized by its quaternary ammonium structure, which contributes to its pharmacological properties. It is typically administered intravenously due to its poor gastrointestinal absorption. The substance has a relatively low solubility in water and is sensitive to light and heat. Its effects can be reversed by the administration of cholinesterase inhibitors, such as neostigmine. While it has historical significance in medicine, its use has largely been supplanted by newer, more effective neuromuscular blockers with fewer side effects. Safety and dosage considerations are critical, as excessive doses can lead to respiratory failure and other serious complications.

Formula: C₃₇H₄₁N₂O₆

InChI: InChI=1S/C37H40N2O6/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)/p+1/t28-,29+/m0/s1

InChI key: InChIKey=JFJZZMVDLULRGK-URLMMPGGSA-O

SMILES: OC1=C2C=3[C@@](CC=4C=C(OC=5C=C6[C@](CC=7C=CC(O2)=CC7)(N(C)CCC6=CC5OC)[H])C(O)=CC4)([N+](C)(C)CCC3C=C1OC)[H]

Synonyms:

• (+)-Tubocurarine
• (13aR,25aS)-2,3,13a,14,15,16,25,25a-Octahydro-9,19-dihydroxy-18,29-dimethoxy-1,14,14-trimethyl-13H-4,6:21,24-dietheno-8,12-metheno-1H-pyrido[3′,2′:14,15][1,11]dioxacycloeicosino[2,3,4-ij]isoquinolinium
• 13H-4,6:21,24-Dietheno-8,12-metheno-1H-pyrido[3',2':14,15][1,11]dioxacycloeicosino[2,3,4-ij]isoquinolinium,2,3,13a,14,15,16,25,25a-octahydro-9,19-dihydroxy-18,29-dimethoxy-1,14,14-trimethyl-,[13aR-(13aR*,25aS*)]-
• 13H-4,6:21,24-Dietheno-8,12-metheno-1H-pyrido[3′,2′:14,15][1,11]dioxacycloeicosino[2,3,4-ij]isoquinolinium, 2,3,13a,14,15,16,25,25a-octahydro-9,19-dihydroxy-18,29-dimethoxy-1,14,14-trimethyl-, (13aR,25aS)-
• 13H-4,6:21,24-Dietheno-8,12-metheno-1H-pyrido[3′,2′:14,15][1,11]dioxacycloeicosino[2,3,4-ij]isoquinolinium, 2,3,13a,14,15,16,25,25a-octahydro-9,19-dihydroxy-18,29-dimethoxy-1,14,14-trimethyl-, [13aR-(13aR*,25aS*)]-
• Tubocuraranium, 7′,12′-dihydroxy-6,6′-dimethoxy-2,2′,2′-trimethyl-
• Tubocuraranium,7',12'-dihydroxy-6,6'-dimethoxy-2,2',2'-trimethyl-
• Tubocurarin
• Tubocurarine (8CI)
• d-Tubocurarine