Clinical data
Identifiers
N-(Cyclobutylmethyl)-8β-methyl-6-methylenemorphinan-3-ol
PubChem CID
Chemical and physical data
C23H31NO
337.507 g·mol−1
3D model (JSmol)
C[C@H]1CC(=C)C[C@@]23[C@@H]1[C@@H](CC4=C2C=C(C=C4)O)N(CC3)CC5CCC5
InChI=1S/C23H31NO/c1-15-10-16(2)22-21-11-18-6-7-19(25)12-20(18)23(22,13-15)8-9-24(21)14-17-4-3-5-17/h6-7,12,16-17,21-22,25H,1,3-5,8-11,13-14H2,2H3/t16-,21+,22-,23+/m0/s1 N
Key:AZJPPZHRNFQRRE-AZIXLERZSA-N N
Xorphanol (INN) (developmental code name TR-5379orTR-5379M), also known as xorphanol mesylate (USAN), is an opioid analgesic of the morphinan family that was never marketed.[1][2][3]
Xorphanol is a mixed agonist–antagonistofopioid receptors,[4][5][6] acting preferentially as a high-efficacy partial agonist/near-full agonist of the κ-opioid receptor (Ki = 0.4 nM; EC50 = 3.3 nM; Imax = 49%; IA = 0.84)[7][8][9] and to a lesser extent as a partial agonist of the μ-opioid receptor (Ki = 0.25 nM; IC50 = 3.4 nM; Imax = 29%) with lower relative intrinsic activity and marked antagonistic potential (including the ability to antagonize morphine-induced effects and induce opioid withdrawalinopioid-dependent individuals).[3][10] The drug has also been found to act as an agonist of the δ-opioid receptor (Ki = 1.0 nM; IC50 = 8 nM; Imax = 76%).[11]
Xorphanol produces potent analgesia, and was originally claimed to possess a minimal potential for dependenceorabuse.[12][13][14] Moreover, side effectsinanimal studies were relatively mild, with only sedation and nausea being prominent, although it also produced convulsions at the highest dose tested.[15] However, human trials revealed additional side effects such as headaches and euphoria, and this was the subject of a lawsuit between the drug's inventors and the company to which they had licensed the marketing rights, which claimed that these side effects had not been revealed to them during the license negotiations.[16] As a result of this dispute, the drug was never marketed commercially.
Psychedelics
(5-HT2A
agonists)
25x-NB3OMe
25x-NB4OMe
25x-NBF
25x-NBMD
25x-NBOH
25x-NBOMe
Atypical structures
25x-NMx
3C-x
4C-x
HOT-x
Mescaline (subst.)
Others
x-DALT
x-DET
x-DiPT
x-DMT
x-DPT
Ibogaine-related
x-MET
x-MiPT
Others
Others
PCP-related
Others
Diarylethylamines
Others
Others
GABAA
enhancers
Others
μ-opioid
(MOR)
Antagonists
δ-opioid
(DOR)
Antagonists
κ-opioid
(KOR)
Antagonists
Nociceptin
(NOP)
Antagonists
Others