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	155203-05-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	110805155;
PubChem CID	101720618;
CompTox Dashboard (EPA)	DTXSID701103363 ;
	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

^ ^a ^b ^c Lattanzi, R; Negri, L; Giannini, E; Schmidhammer, H; Schutz, J; Improta, G (2001). "HS-599: a novel long acting opioid analgesic does not induce place-preference in rats". Br J Pharmacol. 134 (2): 441–7. doi:10.1038/sj.bjp.0704280. PMC 1572965. PMID 11564664.
^ SYNTHESIS AND PHARMACOLOGICAL EVALUATION OF18,19-DEHYDROBUPRENORPHINE Archive.org

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[PMC-1] Lattanzi, R; Negri, L; Giannini, E; Schmidhammer, H; Schutz, J; Improta, G (2001). "HS-599: a novel long acting opioid analgesic does not induce place-preference in rats". Br J Pharmacol. 134 (2): 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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