18,19-Dehydrobuprenorphine

18,19-Dehydrobuprenorphine
Names
IUPAC name
17-Cyclopropylmethyl-4,5α-epoxy-6α,14α etheno-7α-(1-hydroxy-1,2,2-trimethylpropyl)-6β-methoxymorphinan-3-ol
Other names
HS 599
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
InChI
  • InChI=1S/C29H39NO4/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28/h8-11,17,20-21,24,31-32H,6-7,12-16H2,1-5H3/t20-,21-,24-,26+,27+,28+,29?/m1/s1
    Key: XXEUUFWMPBSHCE-NFCPXPRCSA-N
SMILES
  • C[C@]([C@H]1C[C@]23C=CC1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)(C(C)(C)C)O
Properties
Chemical formula
 C29H39NO4
Molar mass 465.634 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

18,19-Dehydrobuprenorphine (HS-599) is a didehydro derivative of buprenorphine. It has about twice the potency of buprenorphine. It has produced a long-lasting antinociceptive response in animal tests.[1]

18,19-Dehydrobuprenorphine never induced conditioned place-preference in test animals, unlike buprenorphine and morphine.[1]

18,19-Dehydrobuprenorphine has about three times higher affinity for the μ-opioid receptor but lower affinity for δ- and κ-opioid receptors when compared with buprenorphine.[1][2]

References

  1. 1 2 3 Lattanzi, R; Negri, L; Giannini, E; Schmidhammer, H; Schutz, J; Improta, G. "HS-599: a novel long acting opioid analgesic does not induce place-preference in rats". Br J Pharmacol. 134: 441–7. doi:10.1038/sj.bjp.0704280. PMC 1572965. PMID 11564664.
  2. ↑ SYNTHESIS AND PHARMACOLOGICAL EVALUATION OF18,19-DEHYDROBUPRENORPHINE Archive.org


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