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18,19-Dehydrobuprenorphine

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.


Column 1Column 2
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
CAS Number.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}155203-05-7 Y
3D model (JSmol)Interactive image
ChemSpider110805155
PubChem CID101720618
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/s1Key: XXEUUFWMPBSHCE-NFCPXPRCSA-N
SMILES
CC@(C(C)(C)C)O
Chemical formulaC29H39NO4
Molar mass465.634 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.

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

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.

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