Altoqualine

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Altoqualine
Altoqualine.svg
Names
Preferred IUPAC name
(3S)-7-Amino-4,5,6-triethoxy-3-[(1R)-6,7,8-trimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]-2-benzofuran-1(3H)-one
Other names
458 L
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C27H36N2O8/c1-8-34-24-18-17(19(28)25(35-9-2)26(24)36-10-3)27(30)37-22(18)20-16-14(11-12-29(20)4)13-15(31-5)21(32-6)23(16)33-7/h13,20,22H,8-12,28H2,1-7H3/t20-,22+/m1/s1
    Key: FPSZSEINEGCRIJ-IRLDBZIGSA-N
  • InChI=1/C27H36N2O8/c1-8-34-24-18-17(19(28)25(35-9-2)26(24)36-10-3)27(30)37-22(18)20-16-14(11-12-29(20)4)13-15(31-5)21(32-6)23(16)33-7/h13,20,22H,8-12,28H2,1-7H3/t20-,22+/m1/s1
    Key: FPSZSEINEGCRIJ-IRLDBZIGBP
  • CCOC1=C(C(=C(C2=C1[C@H](OC2=O)[C@H]3C4=C(C(=C(C=C4CCN3C)OC)OC)OC)N)OCC)OCC
Properties
C27H36N2O8
Molar mass 516.591 g·mol−1
Melting point 144 °C (291 °F; 417 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Altoqualine is an isoquinoline once studied for its potential use as an antihistamine and antiallergic, [1] [2] [3] but it was never a marketed drug. It is an inhibitor of histidine decarboxylase. [2] It was only tested in men, not women. [3]

References

  1. 1 2 C.R. Ganellin, David J. Triggle (Nov 21, 1996). Dictionary of Pharmacological Agents. Vol. 1–2. CRC Press. p. 58.
  2. 1 2 Lallouette P, Mordelet-Dambrine M, Treize G, N'Guyen VT, Dubois AM, Parrot JL (1981). "Pharmacological approach of a new isoquinoline derivative (458 L)". Agents and Actions. 11 (1–2): 41–43. doi:10.1007/BF01991453. PMID   7195643. S2CID   11961698.
  3. 1 2 Bargnoux H, Kantelip JP, Bastide M, Duchene-Marullaz P, Boyer R, Lallouette P, Petit J, Berger JA (1990). "Pharmacokinetic study of a new benzyl-1 isoquinoline derivative (458 L) after oral administration in men". Thérapie. 45 (1): 7–11. PMID   1971461.


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