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Dimethyltubocurarine Iodide

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Chemistry

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Also known as: Metubine iodide, 7601-55-0, Dimethyl tubocurarine iodide, Metocurine iodide [usan], Dimethylchondrocurarine iodide, O,o'-dimethylchondrocurarine diiodide

Molecular Formula

C₄₀H₄₈I₂N₂O₆

Molecular Weight

906.6 g/mol

InChI Key

DIGFQJFCDPKEPF-OIUSMDOTSA-L

FDA UNII

O0U0E87X7F

Metocurine iodide is a benzylisoquinolinium competitive nondepolarizing neuromuscular blocking agent. It is used as an anesthesia adjunct to induce skeletal muscle relaxation and to reduce the intensity of muscle contractions in convulsive therapy Metocurine iodide has a moderate risk of inducing histamine release and has some ganglion blocking activity. Metocurine iodide can be used most advantageously if muscle twitch response to peripheral nerve stimulation is monitored to assess degree of muscle relaxation. Metocurine Iodide is no longer available on the US market.

1 2D Structure

Metocurine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,16R)-9,10,21,25-tetramethoxy-15,15,30,30-tetramethyl-7,23-dioxa-15,30-diazoniaheptacyclo[22.6.2.23,6.18,12.118,22.027,31.016,34]hexatriaconta-3(36),4,6(35),8(34),9,11,18(33),19,21,24,26,31-dodecaene;diiodide

2.1.2 InChI

InChI=1S/C40H48N2O6.2HI/c1-41(2)17-15-27-22-34(44-6)36-24-30(27)31(41)19-25-9-12-29(13-10-25)47-40-38-28(23-37(45-7)39(40)46-8)16-18-42(3,4)32(38)20-26-11-14-33(43-5)35(21-26)48-36;;/h9-14,21-24,31-32H,15-20H2,1-8H3;2*1H/q+2;;/p-2/t31-,32+;;/m0../s1

2.1.3 InChI Key

DIGFQJFCDPKEPF-OIUSMDOTSA-L

2.1.4 Canonical SMILES

C[N+]1(CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C6C(CC7=CC(=C(C=C7)OC)O3)[N+](CCC6=CC(=C5OC)OC)(C)C)OC)C.[I-].[I-]

2.1.5 Isomeric SMILES

C[N+]1(CCC2=CC(=C3C=C2[C@@H]1CC4=CC=C(C=C4)OC5=C6[C@@H](CC7=CC(=C(C=C7)OC)O3)[N+](CCC6=CC(=C5OC)OC)(C)C)OC)C.[I-].[I-]

2.2 Other Identifiers

2.2.1 UNII

O0U0E87X7F

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Dimethyl Dl-curine Dimethochloride

2. Dimethyl-l-curine Dimethochloride

3. Dimethyl-l-curine Dimethoiodide

4. Dimethylchondrocurarine

5. Dimethylcurarine Dimethochloride

6. Dimethylcurine

7. Dmcdm

8. Metocurine

9. Metocurine Dichloride

10. Metocurine Dichloride(1alpha)-isomer

11. Metocurine Dichloride, (1'alpha)-isomer

12. Metocurine Dichloride, (1beta)-(+-)-isomer

13. Metocurine Dihydroxide

14. Metocurine Diiodide

15. Metocurine Diiodide, (1beta)-(+-)-isomer

16. Metocurine Diiodide, (1beta)-isomer

17. Metocurine, (1'alpha)-isomer

18. Metocurine, (1beta)-isomer

19. Metubine

2.3.2 Depositor-Supplied Synonyms

1. Metubine Iodide

2. 7601-55-0

3. Dimethyl Tubocurarine Iodide

4. Metocurine Iodide [usan]

5. Dimethylchondrocurarine Iodide

6. O,o'-dimethylchondrocurarine Diiodide

7. Dimethyltubocurarinium Iodide

8. Tubocuraranium, 6,6',7',12'-tetramethoxy-2,2,2',2'-tetramethyl-, Diiodide

9. Tetrandrini Dimethiodidum

10. (+)-o,o'-dimethylchondrocurarine Diiodide

11. Metocurine Iodide (usan)

12. O0u0e87x7f

13. Metubine

14. Methyl-curarin

15. Dsstox_cid_2944

16. Dimethylether Of D-tubocurarine Iodide

17. Methyl-curarin [german]

18. Dsstox_rid_76799

19. Dsstox_gsid_22944

20. (1s,16r)-9,10,21,25-tetramethoxy-15,15,30,30-tetramethyl-7,23-dioxa-15,30-diazoniaheptacyclo[22.6.2.23,6.18,12.118,22.027,31.016,34]hexatriaconta-3(36),4,6(35),8(34),9,11,18(33),19,21,24,26,31-dodecaene;diiodide

21. Cas-7601-55-0

22. Tubocurarine, O,o'-dimethyl-, Diiodide

23. Metubine Iodide (tn)

24. Nsc-36388

25. Einecs 231-510-3

26. Nsc 36388

27. Unii-o0u0e87x7f

28. Metocurine Iodide [usan:usp]

29. 6,6',7',12'-tetramethoxy-2,2,2',2'-tetramethyltubocuraranium Diiodide

30. Ncgc00181151-01

31. Chembl1739

32. 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-9,18,19,29-tetramethoxy-1,1,14,14-tetramethyl-, Diiodide, (13ar-(13ar*,25as*))-

33. Schembl415745

34. Metocurine Iodide [mi]

35. Chebi:6901

36. Dtxsid9022944

37. Metocurine Iodide [vandf]

38. Metocurine Iodide [mart.]

39. Tox21_112755

40. Tox21_112755_1

41. Db00416

42. Metocurine Iodide [orange Book]

43. 2,2,2',2'-tetramethyl-6,6',7',12'-tetrakis(methyloxy)tubocuraran-2,2'-diium Diiodide

44. Ncgc00263444-01

45. 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-9,18,19,29-tetramethoxy-1,1,14,14-tetramethyl-, Diiodide, (13ar,25as)-

46. Dimethyltubocurarinium Iodide [who-dd]

47. D00761

48. Q20817012

49. Tubocuraranium,6,6',7',12'-tetramethoxy-2,2,2',2'-tetramethyl-,diiodide

50. 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-9,18,19,29-tetramethoxy-1,1,14,14-tetramethyl-, Iodide (1:2), (13ar,25as)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₄₀H₄₈I₂N₂O₆
Molecular Weight	906.6 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Exact Mass	906.16018 g/mol
Monoisotopic Mass	906.16018 g/mol
Topological Polar Surface Area	55.4 Å²
Heavy Atom Count	50
Formal Charge	0
Complexity	1060
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Drug Indication

For use as an anesthesia adjunct to induce skeletal muscle relaxation and to reduce the intensity of muscle contractions in convulsive therapy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Metocurine iodide is a benzylisoquinolinium competitive nondepolarizing neuromuscular blocking agent. Metocurine iodide has a moderate risk of inducing histamine release and has some ganglion blocking activity. Metocurine iodide can be used most advantageously if muscle twitch response to peripheral nerve stimulation is monitored to assess degree of muscle relaxation. As with other nondepolarizing neuromuscular blockers, the time to onset of paralysis decreases and the duration of maximum effect increases with increasing doses of metocurine iodide. Repeated administration of maintenance doses of metocurine iodide has no cumulative effect on the duration of neuromuscular block if recovery is allowed to begin prior to repeat dosing. Moreover, the time needed to recover from repeat doses does not change with additional doses. Repeat doses can therefore be administered at relatively regular intervals with predictable results.

5.2 MeSH Pharmacological Classification

Neuromuscular Nondepolarizing Agents

Drugs that interrupt transmission at the skeletal neuromuscular junction without causing depolarization of the motor end plate. They prevent acetylcholine from triggering muscle contraction and are used as muscle relaxants during electroshock treatments, in convulsive states, and as anesthesia adjuvants. (See all compounds classified as Neuromuscular Nondepolarizing Agents.)

5.3 Biological Half-Life

3 to 4 hours

5.4 Mechanism of Action

Metocurine iodide antagonizes the neurotransmitter action of acetylcholine by binding competitively with cholinergic receptor sites on the motor end-plate. This antagonism is inhibited, and neuromuscular block reversed, by acetylcholinesterase inhibitors such as neostigmine, edrophonium, and pyridostigmine.

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