Laudanosine

Source: Wikipedia, the free encyclopedia.
Laudanosine
Skeletal formula
Space-filling model
Names
Preferred IUPAC name
(1S)-1-[(3,4-Dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
Other names
N-Methyl-1,2,3,4-tetrahydropapaverine
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.018.412 Edit this at Wikidata
EC Number
  • 220-253-2
UNII
  • InChI=1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3/t17-/m0/s1 ☒N
    Key: KGPAYJZAMGEDIQ-KRWDZBQOSA-N ☒N
  • InChI=1/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3/t17-/m0/s1
    Key: KGPAYJZAMGEDIQ-KRWDZBQOBO
  • CN1CCc2cc(c(cc2[C@@H]1Cc3ccc(c(c3)OC)OC)OC)OC
Properties
C21H27NO4
Molar mass 357.450 g·mol−1
Melting point 89 °C (192 °F; 362 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Laudanosine or N-methyltetrahydropapaverine is a recognized metabolite

atracurium
.

Capsule of Papaver somniferum showing latex (opium) exuding from incision. Laudanosine occurs naturally in small amounts (0.1%) in opium.

Laudanosine also occurs naturally in minute amounts (0.1%) in opium, from which it was first isolated in 1871.[2] Partial dehydrogenation of laudanosine will lead to papaverine, the alkaloid found in the opium poppy plant (Papaver somniferum).

Laudanosine is a

muscarinic receptors, which are also involved in epilepsy and other types of seizures.[5]

References

  1. ^
    PMID 12113608
    .
  2. Google Book Search
    .
  3. S2CID 35031924
    .
  4. PMID 15980871
    .
  5. PMID 2536252
    .