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Metocurine Iodide

HCID 24244
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Basic information

CAS
7601-55-0
Standard SMILES
COc1ccc2cc1Oc1cc3c(cc1OC)CC[N+](C)(C)[C@H]3Cc1ccc(cc1)Oc1c(OC)c(OC)cc3c1[C@@H](C2)[N+](C)(C)CC3.[I-].[I-]
InChIKey
DIGFQJFCDPKEPF-OIUSMDOTSA-L
Molecular formula
C40H48I2N2O6
Average molar mass
906.6 g/mol
Monoisotopic mass
906.16018

Overview

Metocurine iodide is an aromatic ether.

Names & identifiers

Preferred name
Metocurine Iodide
IUPAC
(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
English name
Tetrandrini dimethiodidum
Molecular formula
C40H48I2N2O6
Molecular weight
906.63

Names & synonyms

METOCURINE IODIDEMetubine iodide7601-55-0Dimethylchondrocurarine iodideDimethyl tubocurarine iodideO,O'-Dimethylchondrocurarine diiodideDimethyltubocurarinium iodideDTXSID9022944Tubocuraranium, 6,6',7',12'-tetramethoxy-2,2,2',2'-tetramethyl-, diiodideO0U0E87X7FNSC-36388DTXCID802944
Show more names
metubineiodidemethyl-curarinmetocurineiodideTetrandrini dimethiodidumdimethyltubocurarineiodideDimethylchondrocurarineiodided-tubocurarineiodidedimethyletherdimethyletherofd-tubocurarineiodide(+)-o,o’-dimethylchondrocurarinediiodide
(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(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;diiodideRefChem:56447231-510-3NSC36388MetubineMetocurine iodide [USAN](+)-O,O'-Dimethylchondrocurarine diiodide

Properties

Computed structural properties

Topological polar surface area
55.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
8
Rotatable bonds
4
Heavy atoms
50
Formal charge
0
Complexity
1,060

Experimental & physicochemical properties

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point267-270

Physicochemical properties

alpha
22 · D22 +148 to +158° (c = 0.25)
EWG's Food Scores
1 · 1
FDA UNII
0 U0E87X7F · O0U0E87X7F
RIDADR
3249 · 3249
HazardClass
6.1 · 6.1(b)
PackingGroup
III

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

ridadr
3249
hazard_class
6.1(b)
packing_group
III

Chemistry & industry

Pharmacology

Protein Binding35% in plasma
Pharmacodynamics · 1 item

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.

Mechanism of Action · 1 item

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.

Biological Half-Life3 to 4 hours
MeSH Pharmacological Classification · 1 item

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.

Applications · 3 items

UsesMetocurine Iodide is used as Zika virus protease inhibitor.

UsesNeuromuscular blocking agent.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
7601-55-0
PubChem CID
24244
DTXSID
DTXSID9022944
ChEMBL
CHEMBL1739
ChEBI
CHEBI:6901
UNII
O0U0E87X7F
EC Number
231-510-3

General DescriptionMetocurine iodide, ( )-O,O -dimethylchondrocurarine diiodide (Metubine iodide),is prepared from natural crude curare by extracting the curarewith methanolic potassium hydroxide. When theextract is treated with an excess of methyl iodide, the ( )-tubocurarine is converted to the diquaternary dimethylether and crystallizes out as the iodide (see “TubocurarineChloride”). Other ethers besides the dimethyl ether havebeen made and tested. For example, the dibenzyl ether wasone third as active as tubocurarine chloride, and the diisopropylcompound had only one half the activity. For comparison,the dimethyl ether has approximately 4 times theactivity of tubocurarine chloride.The pharmacological action of this compound is the sameas that of tubocurarine chloride, namely, a nondepolarizingcompetitive blocking effect on the motor end plate of skeletalmuscles. It is considerably more potent than d-tubocurarine,however, and has the added advantage of exerting much lesseffect on respiration. The effect on respiration is not a significantfactor in therapeutic doses. Accidental overdosage iscounteracted best by forced respiration.

Upstream & downstream products

Upstream raw materials

IodomethaneCURARE

Additional notes

DefinitionChEBI: Metocurine iodide is an aromatic ether.